Top 10 Biggest “What Ifs” in Chicago Cubs History! | CHGO Cubs Podcast
Coming up next on the CHGO Cubs podcast presented by Toyota and Bet 365. Today is rank week. We are ranking the top 10 whatifs in Chicago Cubs history. What? CHO Cubs next. Heat. Heat. Hey Chicago, what do you say? This is the CHGO Cubs podcast driven by Toyota. Let’s go places in bet 365. Whatever the moment, it’s never ordinary. Use the code CHGO365 at signup. Uh, hi everybody. Luke Stuckmire, Joey Castropolis. We have Sarah running the ones and twos. Uh, it’s the Stuck and Joey show today as we go through rank week. This is one of This is one of the slower weeks of the year uh to be factual. Summer’s in full swing. Nothing wrong with that. But rank week makes it tolerable because I like to think of things in numbers. I don’t like math, but I like to think of things in numbers. So, we’re going to start with number 10. It’s the whatifs, right? Biggest whatifs in Cubs history. We’ll start with 10 and we’ll work our way down to number one. If we have time, we’ll do some honorable mentions that maybe didn’t quite make our list, but you could certainly put in a list if you expand it out to 15 or more. All right, so number 10, 10th biggest what if in Cubs history from our perspective. What if Mark Cuban had purchased the Chicago Cubs? Luke, this is a great way to start the list. I love the fact uh that when uh when it comes to hypotheticals, you call me in from the bullpen on this one. Right. And if Mark Cuban had purchased the Chicago Cubs now, from what I understand, he put in a bidding for the team in 2007. Right. Rick Rickettts ends up purchasing the team in 2009. So, does a whole lot change in terms of them trying to push it forward to try and finally get that World Series? I don’t think it changes because I think Cuban would have been a very aggressive, ambitious owner. Uh, we all know with the Dallas Mavericks, their locker rooms would have been incredible. uh the renovations on the internal of the internal of Wrigley Wriggley would have been fantastic, but it does open up a can of worms of a lot of different questions of what would the new version of Wrigleyville actually looked like. I want to start there before we go to the team. What do you think the new version of Wrigleyville Shark Tank would have been live from the ballpark? That would have been the first thing. You know, people have been pitching their ideas to Mark Cuban. He wanted to buy the team for all the same reasons the Ricketts family did. some financial, some obviously more emotionally tied than that. He used to go when he went to Indiana, he would like to make road trips to Wrigleyfield. Loved Wrigleyfield and the vibe and all that stuff and knew that it was a hidden gem. I agree with you when I say the first part of Rickett’s ownership probably wouldn’t have been that much different than Cuban ownership. I don’t know how it could be any better. If you had any problems with the Ricketts family up to 2016, I’m not sure what they were. Maybe they were political or something like that. But if you’re talking strictly baseball and rebuilding Wrigley Field, they put all their money into rebuilding Wrigley Field. I assume Cuban would have done that, right? 100%. He would have done a lot of his pockets were deep. And I think in terms of the neighborhood, I think he would have had the same the same push to turn the neighborhood over the same way that the Ricketts family did. You know what would have been different? The flare, the eyeballs. Like the Ricketts didn’t do any of this with like fireworks and flare. Mark Cuban is a showman. If anything, right? If you’ve ever seen a Mavericks game when he was the owner of the Mavericks, it’s like they’ve miked up the ball hitting the rim so loud that when it goes bonk off the rim, you think like the buildings caving in and it’s like a rock concert in timeouts. like some of that charm maybe of Wrigley Field would have changed and some would say it already has under Ricketts, but I think as far as pouring money in, the Ricketts did every up to 2016. I don’t know too many people through the World Series that had problems with the Ricketts family. And I think that’s probably where the similarities end, right? Because then if you look a little bit forward, obviously um they did have some human resource uh problems with the Dallas Mavericks franchise while he was the owner of the owner of the Dallas Mavericks. We can’t get away from that. But if we move it a little bit closer before we just even get on the field, would have Mark Cuban have been like behind home plate screaming at the umpire every single home game the same way that he would attend his Dallas Mavericks games? What kind of an owner do you think he would have been as cuz he seems like a guy who likes to be a bit participatory? I’ll tell you who he would have been. He would have been he would have you remember when uh Theo sat in the outfield in the bleachers with the glasses on? We would have seen Cuban in the bleachers. Would Cuban and Panella gotten along? Uh, no. Uh, we would have seen Cuban in the by the by the on deck circle a lot more. We would have seen him doing a lot more stuff on uh than Comcast Sports Net, CSN, NBC Sports, Chicago, because he would have been purchasing part of that, too. Um, and I think all of those things would have had a little more flare. Now, he offered his bid was the highest bid, 1.3 billion, but it’s got to get cleared. Baseball ownership’s different. He’s got to get cleared by the commissioner and the owners. And the commissioner was Bud Celig. And he’s Jerry Reindorf’s best buddy. And if you think Jerry Rinddorf wanted Mark Cuban coming into the Cubs when he already felt like little brother, I can guarantee you that was Mark Cuban could have offered two billion and baseball would have said, “Uh-uh.” So the next question that I have in this what if scenario is as we all know Mark Cuban front-facing personality in many ways with the Dallas Mavericks enjoyed and reveled in perhaps being the face of the franchise when he had quite a more quiet go about his business star like Dirk Nitzky. My next question for you is would Mark Cuban have been able to land Theo Epstein? because I’m going to go out on a limb and I’m going to say no because I think the reason why Theo said yes to the Rickettts family wasn’t just money but Ricketts also said I’m getting out of the way. You are literally running the show and calling the shots. This is my checkbook and let’s talk again in six months. It’s tough. Uh Cuban’s a smart businessman and when you see somebody that can do something like that, we’ll never know the answer to that. Would Theo have come here? Would Madden have come here? Jed, all of them. Like we don’t know the answer. Do I think he would have saved Wrigley Field and rebuilt Wrigley Field? Yes. Would they have won the World Series? We’ll never know. We’ll never know. And so that’s that is why it is number 10 on our list. Number nine. What if Greg Maddox never left via free agency? Well, now this one hits to the core of my childhood. I was going to say you’re setting me up, but you take this one first. This one, uh, okay, he left as a 26-year-old Sai Young winner. He was he was really good when he broke onto the scene, but by 26 he by 26 years old, he’s the Sai Young winner. He’s already done the sliding across the tarp on the first ever night game. All of those things, it was the first of his four Sai Youngs. And then it got to the point where Larry, who was the GM, apparently made an offer, but he was offering more like money for a good pitcher, not a superstar pitcher. Well, we all know Greg Maddox. Some I personally consider him easily one of the five greatest pitchers of all time. Some some say maybe the greatest pitcher of all time because he did it by literally pitching, not throwing, pitching. And what he did was incredible. So, makes this offer and Maddox was looking for more money and wanted to stay here, but the Cubs weren’t interested in bucking up the big money back then. Sound familiar? Yeah. Yeah. So, I don’t know. I Well, he would have retired. He would have gone into the Hall of Fame as a cub. That’s the first thing. He would have been Ray Bourke is what would have happened. He’d be on year 20 or 21 and he’d be ring chasing because the great, wonderful Greg Maddox wouldn’t have a ring on his finger. And I’m with you, man. I think Greg Maddox and maybe Randy Johnson, I think, are the two greatest pitchers I’ve ever watched in my lifetime live. Right. And we’re all under the constraints of father time, so I can’t go that much farther back. But in my opinion, if Greg Maddox had never left the Cubs, I mean, this is like my formidable formidable years of being a Cubs fan, coming home from school, it’s the seventh or eighth inning, and Jim Bowlinger has given up the lead. Jos Guzman has given up the lead. Kevin Foster has given us all the hope in the world and not working out. I mean, I I don’t know. No, I guess like the other question would be if they had signed Greg Maddox, would they have been more open to signing other players other than Jeff Blowser in the ‘9s? And I don’t see it happening. So, I think Greg Maddox would have been an amazing pitcher on a terrible team. And I Well, I don’t know. Maybe we’d be better 98. Do we have a shot if if Greg Maddox is our pitcher in 98? I I agree that he would have still been a great pitcher because some people say, well, it’s the organization, it’s the manager, it’s the fit. He got to pitch with Smoltz. He got this, you know, all those great pitchers that the Braves had tulled of Leo Mazone, right? And he got to be there with Bobby Cox and yada yada yada. And would it have been different with the Cubs? He was the Sai Young. The question is how would he have impacted a young Carrie Wood even more? Yeah. Right. Like does Carrie Wood approach the game differently? Do other guys like he came back in 2004 and when he came back in 2004 it was too late. It was too late to write that wrong. Um, so Greg Maddox, what happens if he never leaves? That is number nine on our greatest what-ifs in Chicago Cubs history. Number eight, what if the 1969 Cubs didn’t collapse? Okay, so for those scoring at home, just really quick to add to add some context to this, right? Neither was I. Well, neither of us were alive, but uh here’s here’s what we have. We have uh in September the Cubs go nine and 17. They lose 11 of their they lose 11 of their first 12 games of the month. Can you imagine doing postgame pods going one and 11 to kick off September? Luke, we still we then would not be alive. Uh the Mets surge meanwhile they went 23 and seven in the month. Uh while the Cubs faltered, they blew a sevengame lead over the Mets. It completely evaporated. It ended up being eight games behind the Mets. So they went from seven up to eight back. Um, and I look, the only thing that I could probably say is for all the sad dads out there, uh, do we have happier dads and happier uncles and aunts and those people that had to live through that time and and and be branded, uh, with that type of trauma and scar? Would they feel that certain way if they don’t blow that lead in ‘ 69? This one has another like this has like um a little A and B next to it because it’s also like what if they weren’t put in the Eastern Division. This was the first year of divisional play in baseball. It was just National League American League and the Mets who were fairly new. I think this was like their eighth season in baseball had never finished higher than ninth place. So nobody expected the quote unquote miracle Mets to do this anyways. And of course, there’s the story about the Cubs actually playing the Mets and the Black Cat comes into the on deck circle. Now, if you want to believe in that sort of stuff and Billy Goats and all that, whatever. All I know is most people probably blame part of the collapse, at least on the Cub side, on Leo Dorcher, the manager, pushing his players too hard, playing them too much, and they were gassed and they ran out of gas. Sure, but the other team still has to be spectacular. And the Mets went 23 and seven. They won 38 of their four final 49 games. That’s a crazy run for a team that had never finished better than ninth. So I don’t know. Let’s say they they don’t collapse and they beat the Mets or they hold on just barely. Do they beat the Orioles in the World Series? Because the Mets beat the Orioles four games to one. The Orioles were the powerhouse team. That was the team everybody expected to win the World Series. I don’t know if everybody expected the Cubs to get there and beat them, but now considering this lucky run that the Mets went on and the Miracle Mets and all this stuff, you look at it and say maybe the Orioles were primed for a team like that. Maybe they were primed for a Cubs team with Ron Santo. All I know is if the Cubs don’t collapse in 69, Ron Santo has a lot less hate for the Mets the rest of his life. And I will also say there’s a lot more probably sons and daughters in our case uncles named Ron or Santo, right? I mean, he is a legend in this town. You can’t get around that one. And also that maybe opens up the door to maybe Ron San make the Hall of Fame a little bit sooner. Oo, if he’s becomes a World Series champion, win the World Series. That’s a good one. See, so now there’s A, B, and C. Maybe Santo is an earlier Hall of Famer, right? And the large part about thinking about these moments that I’m not a part of cuz I wasn’t breathing uh the oxygen in the air is if you go nine and 17 and let’s say you lose the World Series to the Orioles. I guess you have the penant. You take the penant off of this. And part of this exercise specifically for when we’re talking about this and you’re watching as Cubs fans is how do you take your trauma, right? Like these things, you know, the Black Cats, the Billy Goats, 69, we’re getting into a couple more of them as we move along this list here. Is like would you, now that we have a World Series title, would you trade it all? Would you trade some of this trauma and take some of it away and have them be more successful somehow? And I don’t know if I would. For me, I enjoyed the trauma that they they suffered in ‘ 69 because I wasn’t there. Yes. So, it only added to the lore of how great it became in 2016 was only bigger because of the black cat and the 69 Cubs. Sorry, Dad. We’ll go We’ll go next down the list. It’ll be another old one coming back that could have also impacted the Cubs in the 60s. But first, a word from our sponsors. Hey, whatever the moment, it’s never ordinary at Bet 365. New customers now get $150 in bonus bets when you bet $5, win or lose. Sign up. Use the code cho365. Deposit $10 and place a bet for $5. Get $150 in bonus bets if you bet w if your bet wins or loses. There’s also the MLB early payout offer. 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We just had what if the old 69 Cubs hadn’t collapsed? It’s a big what if. I got another one that’s a little more our age. Joey number seven. What if the Cubs had acquired Justin Verlander instead of Joseé Kintana? This one I think is one of the biggest regrets of the Theo Epstein era. One of the most difficult things to digest about this was that Justin Verlander wanted to be a Cub. Yes, he was begging for it. Yes. So much so that he want the the Cubs got involved very late, but they didn’t have the money left. They didn’t have enough money left to do it is what Jed has said. He says, “Yes, we have regrets now.” Jed says, “Yeah, we have big regrets.” Verlander was hoping the Cubs could figure it out and waited until the last minute before he took that offer from Houston because he had to approve a trade. Yeah. And the most difficult part about it is for those that might not remember in 2017, uh, he went 5-0, 1.06 RA, 34 innings pitch. Uh, I’m seeing only four runs allowed, only 17 hits, uh, 43ks, and then obviously what he did in that playoffs. And this is one of now we’re really getting into kind of and maybe this cuz we live through it. We’re kind of getting into the meat now of the whatifs on this one because I find this one incredibly intriguing where if we all go back and think about the Cubs trying to defend their World Series title in 17. You know what was the prevailing narrative walking out of that is that they ran out of gas, right? That national series grinded them down into dust and they had nothing left when they took over took on the Dodgers who were good. They were great, right? But it’s a great what if of who’s on the mound. Is it John Lackey or is it Justin Verlander to kick off that series in Los Angeles. So when you look back at that one, I’m not going to say that I think the whites the Cubs would have gone like back to back, but I would like to think that the window would have stayed open a little bit longer. Listen, my buddy Cap always says that Kintana was the Buick. They thought they were getting a Maserati. Verlander is a Maserati, period. Some people thought he was running out of gas. He wasn’t running out of gas. His Hall of Fame career kept ripping right through his time in Houston. The Cubs not forget 2017 in reality. Like if you want to go beyond like what if they had Verlander instead of Kintana, lots of things changed. They never probably signed Darvish. No, they never even go the Darvish route. So that experiment doesn’t happen. You have Arietta, you have Lester, Hendris, and Verlander. with Dylan C’s still in your system too as well. We don’t know if he was they thought he might have been a bullpen guy, right? They never know if he would have been a front of the rotation guy, but he’s still in your system. The Astros gave up three of their top 11 prospects. I looked at the names. They’re nobodyies. So, you never know if the prospects you gave up. Now, maybe Eloy still would have been on there. Who knows? I don’t know what the names were. All I know is that when Jed Hoyer was asked, he honestly just said, “Yeah, we have regrets.” That’s that’s the big regret. How did we not get Verlander when he wanted to come here? It’s like they had made all these moves and they and they weren’t thinking ahead far enough to be like, “Oh, Verlander wants to be here.” Hey, it is one of it. This one is fun because it is a bit of one of those like pebbles that gets loose and then the dam sort of breaks open of then I’m with you. Did they sign U Darish? Did they sign Tyler Chatwood? Did they sign Brandon Moral? Does Theo Epstein really come to the conclusion that the offense is broken in 2018 if maybe a couple more of those games were two to one wins instead of three to2 losses? Does the narrative flip a little bit? I get that the offense needed a complexion change somewhere along those roads, but when you have a stud like Justin Verlander and a guy, you know, an ace, we’ve only seen so many aces in this town on the north side in the 21st century, right? Yeah. Wood Prior, John Lester, Jake Aretta, and that could have been Justin Verlander. And that’s what we’re always going to have to think about and deal with. I think they would have had a shot to beat the Dodgers in 2017 with Verniner. Obviously a better shot than they did with Kintana. I don’t know about beyond that. Obviously the pitching’s way better, but if the young guys still don’t develop the way the Cubs all thought they were, like if Chris Bryant’s back doesn’t start, that doesn’t impact Chris Bryant’s health. Yeah. That doesn’t impact Jav’s playing for is he gonna go down this path or is he gonna go down? It doesn’t impact Schwarber. It doesn’t impact Albert Elmore. It doesn’t like it doesn’t impact any of those guys. So, I’m not sure, but I think 2017 would have been a much better chance at a repeat. I think there’s a really good chance they went at least backtoback World Series. Maybe they don’t win the second one, but they’re there. And I certainly like the rotation a lot better with Justin Verlander than I do with Kintana. It’s just obvious. The final question I would have had with that would be if we had made that deal, how long would he have been able to stay in a Cubs uniform? I don’t know. Because eventually he would have been priced out, right? I mean, he ended up signing what, a $40 million a year deal with New York. I mean, so the window might have actually stayed in the same capacity of that 2017, 2018, 2019 window, but damn it, I would have liked to seen it. Sure. They tried and if you end up having to trade those guys because the young guys aren’t going. Imagine the hall you got back from Verlander, right? Would have been pretty good assets. All right, number six. What if Leon Durham fields the ball in 1984? Again, back to my childhood, but this one is a stake right through the heart. It’s It’s like Dracula standing right here and sucking the blood out of my neck. Dracula with those glasses on. Leon Durham. Bull Durham. Uh, seventh inning, game five, NLCS. Tim Flannry reaches base and they score the tying run to make it 3-3. The Cubs had a lead in the seventh inning of game five. Remember, these weren’t seven game series. This was it. This was the game to go to the World Series. They were on the verge of the World Series. All they had to do was get seventh inning, eighth inning, ninth inning, and he boots it. And then it should have been runner at third, two outs. Now, they still had Gwyn and Garvey coming up. So, I can’t say for sure the Cubs go on and win the game. But all those people that want to talk about the stuff in 03, to me, this is this is right there with it. And I know we’ll talk about 03, but I’m telling you, they were close. They were close. They had a lead in the seventh inning of game five. and they would have faced the Tigers who were a good team, like a 102- win team in the World Series. Man, I I’m ch I watched those I sat there as a kid in middle school. I watched those first two games at Wrigley Field. The Cubs crushed the Padres’s. They were going to be able to hang with the Tigers. It was not going to be the same World Series. Well, from what I remember was uh that that was the team with the mojo, right? I mean, they had Rick Suckliffe throwing with his hair on fire. I would have loved to have seen Rick Suckliffe, Jack Morris, game one of a World Series. That would have been amazing. U just real quick, is is that sports fan Luke Stuckers? Is that like top five darkest day? Is that is that the one that stays with you? Is that it? Yes. I remember like I was off working by the time 03 happened. I was off living in Texas. 84 was like the height of my Cubs fandom as a kid. Right. Yeah. My dad didn’t speak for like 10 days after that game. And my dad is my dad was not like this emotional like, you know, super hyper crazy Cubs fan. I love it. Dad was the house was quiet for 10 days. Yeah. That was the first time in my life I knew the Cubs could even be good was 84. And then for it to see that, for that to be the way the season ended was just like, oh man, maybe there is something to this black cat. Maybe they’re not meant to win. Maybe it’s never going to happen. Maybe it’s never going to happen. I grew up with that in my life that you know what? Maybe it’s never going to happen. Silver lining about 84 though, really quick. It did make me a better baseball player as a little league player because I tell you, every single coach that I ever had told me not to be Leon Durham. Keep your glove on the ground and keep it on the ground until that ball gets into your glove and you throw to first base. So, shout out shout out to that. At least it made me a better ball player. But man, that’s um that that one’s tough. Yeah, Buckner and Durham so close together. 8 84 was a tough year in Cub fandom, let me tell you, cuz they were electric. All right, number five on our biggest what-ifs in Cubs history, rank week here at CHGO. What if the Cubs never traded Hall of Famer Lou Brock? Well, the E. Okay, first of all, it was a sixplayer deal for Ernie Brolio. Yeah, exactly. Brock immediately becomes a super St. Louis. He hits 348 that rest of the season and he leads the Cardinals of all teams to a World Series title. Okay, that was June of 64 when they traded him. The word was like for people that aren’t sure about this trade, Lou Brock was one of the greatest base runners of all time. And from what I again not alive in 64, but from what I was told from people that were around, Cubs fans will say, you know what, I don’t know if Lub Brock would have been exactly the same player with the Cubs because they didn’t necessarily embrace his bold base running. The Cardinals did and they encouraged it and he blossomed into this player. Now, that’s that’s a pretty quick turnaround to be hitting 348 the rest of the season with 33 stolen bases after June. So, I’m going to say he would have been that player anyways. And if you’re asking me really, what if they didn’t trade Lou Brock? Well, the Cubs added Fergie Jenkins two years later. So, take Brolio out of the rotation. Put Lou B. Put Fergie Jenkins in there. When you have already Banks and Santo and Williams, you realize what you have there. That’s three Hall of Famers. It’s a pretty good team. You add a fourth Hall of Famer to the team and and and Fergie is five. You’re telling me they wouldn’t have figured it out? The 60s would have been a lot better as a Cubs fan. again wasn’t around for him, but those mid60s would have been a lot better than they were with Lou Brock. Yeah, that’s the the one that I think about now just in 2025 is when you go down to Gallagher Way would be, “Hey honey, can I get a picture next to the Samberg? Can I get a picture next to the Banks?” Yeah. Oh, yeah. Can I get a picture next to the Brock? That’s probably the one that I that I think about a little bit. And the Fergie and would his number be on a flag somewhere up on a foul pole. The other one too as well, and this one is great right now because the trade deadline’s right around the corner. Um, this is is this like ground zero for never trade in your division. Is this one of those great tall tales? No. No, it’s not. But you know what really bothers me even more about it? Again, wasn’t alive for it. Shouldn’t bother me. The Cardinals won the World Series with the guy and he had a great career with them. Not only does Lou Brock stay with the Cubs in a in our scenario and join Banks and Santo and Williams in a lineup, he’s not on the Cardinals. Yes. They’re not winning the World Series in 64. Mhm. So, you’re taking away from your hated rival and you’re putting this great player. It hurts. It hurts. It’s a bad trade. It’s a bad one. It’s it most people consider it the worst trade in Cubs history. Uh thankfully, what was it in 1982? They did trade what Ivon De Jesus for a certain guy named Ryan Samberg, which is a good one, right? We like to tip our cap to that one. It’s either that or the Arietta trade. Best trades in Cubs history. For me, the Arietta trade gets us a World Series. So, and I I love Rhino, don’t get me wrong. Like childhood hero, one of the great 23s in Chicago history. Um, but yeah, you know, when we’re throwing that stuff out there, too of Yeah, just go ahead and trade soand so for Sunny Gray or is Freddy Peralta available and Mitch Keller right now. I know, Joey. Can never happen again. Yeah, we we have more coming up in our whatif list, but uh and we will get to the top five. I’m telling you, some of these are going to just rip your heart out. There’s no question about it. But first, a word from our great sponsors. Hey, I got to talk to you guys about Sunnyside Cannabis Dispensary. It’s your home for judgment free cannabis shopping. A place where all kinds of visitors are welcome to explore, discover, and purchase a wide array of high quality products. Sunnyside, they’ve got everything you need to elevate your summer. What are some of the amazing features that makes the brand or product awesome? Well, it’s a one-stop shop for all your cannabis needs. 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This gets real now. Some of it’s painful. Yeah, frankly, most of it’s painful. Possibly all of it will be painful. Number 10 was what if Cuban had purchased the Cubs? What if Number nine, what if Greg Maddox never left? Number eight, what if the 69 Cubs don’t collapse? Number seven, what if the Cubs got Verlander instead of Jose Kintana? Number six, what if Leon Durham doesn’t boot the ball in 84? Number five. What if the Cubs never traded Lou Brock? Do you see a theme there, Joey? Um, I do. Pain. Pain. Mr. T used to say pain. That’s what this is. It’s all pain. Well, an hour of pain. After this next one, we got a couple doozies for you. So, uh, take your take your ibuprofen now or your sunny side. Get ready. All right. Number four, our fourth biggest what if in Chicago Cubs history. I love to do this. Sammy kiss at the end of every show. What if the Sammy Sosa trade with the White Socks never happened in March of 1992? A young Luke Stucker sitting at Valparezo University in his dorm room and he hears of this trade while listening to sports radio sitting on the floor and he says, “Man, I like George Bell. I don’t know if Sammy Sosa is this good.” Well, it worked out. You want to talk about great trades in Cubs history? We mentioned Sanberg and Arietta. Sammy and 92 is a pretty good one. Uh if we also remember this was a perm for a perm tray. Remember they both had beautiful, wonderful perms back then. Uh I also remember this. I was sitting on a recliner chair at my aunt’s house. She had just gotten a water bed, so it was pretty rad at the time. And I remember like Sammy was the original Panther on the Southside and they traded him over. And I remember also watching his very first game. I believe he was playing center field at the time. And what did Sammy do? Oh, did he miss the cut off man and he just sailed the ball right to the back to the back fence. And he was young, he was wiry, he was fast. Uh he eventually developed a little bit of power. The other one that I like a little bit, just a little bit. The other one I like to think about too is remember he got hit on the hand. He was sitting at 40 home runs. Got hit on the wrist. I think that was 96 or 97 before the 98 year. Um I, you know, I’m kind of ready for my first hot take on this one. If the Cubs never trade for Sammy Sosa, I don’t think we have a World Series title. I don’t think it happens. Why? Because Sammy, he wasn’t around for it. I understand. But Sammy was the catalyst that created the momentum that eventually pushed them to the edge of not only selling the team to the Ricketts, but also creating this the lovable loser thing was something that was embraced. And then in 98 it was celebrated in a strange way that maybe this is their way out of it. He was a part of the 2003 team. And after the 2003 collapse, him being a part of it and one of the key cogs in that offensive lineup. Two or three years later, what do they do? They’re reloading the chamber and trying to do it again with L Panella in 0708. Then they sell the team in09. I just don’t know what does Wrigleyville look like if Sammy 98 doesn’t matter. Two two things changed Wrigleyville. Sammy Sosa and Harry Kerry 100% and together right together. What’s that famous Sports Illustrated uh cover article that like the party’s here or something like that and it was a loaded wriggly field and that was when the kind of the national the conventional wisdom of like the Cubs are never going to world win the World Series. After 98, I think we started having those conversations of could they possibly one day win the World Series. And I think Sammy is a huge part of that. And I just I I don’t know what Cubs Wrigleyville what the organization the franchise looks like if he never plays and doesn’t hit what you have here 545 home runs in a Cubs uniform. Yeah. Well, I think I think the story is different for a lot of people, right? like we just we we glossed over the fact of he was wiry. He was wiry at the time. That’s right. Um things would have been different for the Cubs. Would the home run chase have been different if he’s doing it in a White Sox uniform against Mark Magguire and a Cardinal? Part of the charm of that was arch rivals literally playing in the same game. That’s a great point. Trading bombs every day. You’re not division. You’re not going to see that if he’s on the White Socks. Some would argue if a tree falls in the woods but nobody’s there to see it, did it actually happen? I don’t know. I don’t know if it would have happened. Like, would Sammy have been the same on the south side? Would he been would he have been enough to turn the socks into what the Cubs are now? Uh, I don’t know about that, but it’s not inconceivable. Imagine Frank Thomas and Sammy Sosa in the same lineup for the primes of their career. Yeah. Like they played together very briefly, very briefly at the beginning, but remember Sammy was wiry and just this kind of freegoing guy. Frank Thomas is one of the greatest hitters in the history of the game. And does Sammy get away with some of his stuff as a member of the White Socks if he that he got away with the Cubs? Now, finally, it caught up to him. They smashed his boom box and they had enough and all that stuff and he’s apologized for some of it. But I got to tell you, I don’t know. Sammy admits to mistakes. He hasn’t said the sword yet. Yes. But he’s now admitted to mistakes. Said a bunch of other letters of I did whatever I can to play. I’ve had conversations. I know one guy that’s mad about the steroids era and his name is Frank Thomas. Big Frank doesn’t like that he lost an MVP to somebody that was doing steroids. So I wonder how is it different if Sammy gets in finds out about this steroid thing in the socks clubhouse with big Frank because Sammy didn’t want to be challenged. But let me tell you, Sammy, even in his biggest form, isn’t the size of Frank Thomas. No. And it’s curious, too. I mean, you know, I know we’re talking Cubs here, but if you think about the Southside back at that time, they had Tim Reigns in left field. They had Robin Ventura at third base. They had Julio Franco at DH, and they were kind of rotating right fielders for a long time between Ellis Burks and Danny Tardal during that time. So, Sammy would have fit right in in that right field area. But yeah, the the socks might have won a World Series sooner than they did with with Frank and Sammy in the same lineup. That’s all I’m suggesting. Yeah. How would it have changed the Cubs greatly? Wriggley Wrigleyville probably is a different look. Heck, baseball might be different. That was They were the two guys that saved baseball. I don’t know if it’s the same. So, that’s a huge what if. That’s why it is number four on our list. All right, number three. Oh, boy. All right, let’s I need to stretch. This one hurts again. I don’t even know. This is mine. This is your You’re 84. This is mine. This is a list that I don’t know when we put it together, the bosses said, “Let’s do a what if list for rank week.” Were they trying to make me weep? Because most of Cub’s history is weeping. You know, only recently was it good. There was a there was the the golden era, but most of my life was weeping. I need a bib for this one. Number three. Mhm. What if Mark Prior and Carrie Wood stayed healthy? Oh, the dynamic duo. What we had going like we want to talk about what if Maddox stayed and stuck around and they had Maddox in his prime and all those things. You had two of the best young pitchers in all of baseball. Maybe you had your Maddox and your Glavin, but they could not stay healthy. Prior’s career ended at age 25. I covered I covered those early those those teams in like 0405. Like I saw Mark Prior doing the towel drill more than I saw him pitching in games. Right. I read that so many times in 03. They were both so good and even though it got away from the Cubs as we know and we will talk about the future was so bright with these two guys that you thought they were going to mow down batters for the next decade together and it didn’t happen. And it was the first lesson in my life that taught me, boy, pitchers can get hurt. And that’s a problem. And it hasn’t changed in baseball yet. No, it hasn’t. No, it hasn’t. And we’re not exactly doing the pitch counts that we used to uh back in the day either. Uh, you know, you mentioned you mentioned Maddox and and in many ways the way Prior’s at times people thought were flawless mechanics. Yeah. and his control was very Maddox like and Carrie Wood very much was of the Ilen generation of the Roger Clemens and Nolan Ryan’s that I grew up on and what did Nolan Ryan do? He pitched till he was 45 and Roger Clemens another guy with a different story altogether also pitched deep into his career. I’d love to even boil it down even more. What if Mark Prior doesn’t run into Marcus Giles heading into second base and I just wonder what would happen with that 2004 season? But that is part of that that is part of staying healthy. I don’t know. Like that was a that was a big deal in 04. Prior did have some mechanics problem. Like everybody thought it was perfect but it wasn’t. Yep. Carrie Wood when he throws his strikeout game at Wrigley Field. Could somebody envision boy this guy might have this? This is so incredible. How is his arm going to hang on? He had all kinds of weird stuff, right? Yeah. like he had he had just weird injuries and and then he ended up going to the bullpen and he plays with other teams. This was a dynamic duo and I know most people I I don’t want to say most people there is a large section of Cubs fans that put 100% blame on Dusty Baker because there were times where these guy you mentioned pitch counts. Mhm. There were games where some of these guy these guys were throwing 130 140 something you would never game two of the NLCS right aren’t we up we’re up 8-1 and we still have Prior going out there pitching and I think that’s the big one that they talk about preservation and pitch counts things are a little bit different today I don’t know if it’s a real thing if it’s factual in this case whatever happened to Prior and Wood it changed the future for a long time. Yeah. See, I I can’t like buy into that personally because then that opens up the sliding doors of what if John Lester came in in relief in game seven, you lose game seven, then John Lester gets hurt for the rest of his, you know, you can play that game with a lot of different kinds of scenarios. It’s the whole show. No, get ready. That’s number one. That’s number one coming up. Uh, and the other part I think about too is that what if just one of them has stayed healthy? Yeah. What if just one of them would have been a front of the rotation guy as Carlos Sbrano was coming up. Um, and we were having that is he an ace type of conversation. Zimbrano and Prior pushing forward. You could still go out and get Maddox. You still would have had one more year of Matt Clement. When we talk about Prior and Wood staying healthy because Wood ended up coming back and you’re correct, he was a closer for a couple years and contributed and Prior just never came back. I I just wonder if just one of them if just one of them was able to come back and would Mark Prior be a pitching coach today because he had to go through all different kinds of trials and tribulations, right? Well, I mean, if you want to expand that far, you can look at it and say, “What if they stayed healthy?” Well, if they both stayed healthy, you’re looking at potentially two Hall of Famers. That’s the type of talent they had. And would the Cubs have signed them? Well, that I I don’t know. I don’t know what the answer to that is, but Prior and Woods health um was a big part of the collapse for the Cubs for a while, and it it looked like it was going to be the glory days. Yes, it really did because that pitching staff when Zimbrano came along it was like wow they they have so much young pitching that’s elite that they don’t know what to do with it and then all of a sudden it was Zimbrano. Yep. Not that there’s anything wrong with that, but it became a problem. All right, so we’re down to our final two and maybe a little bit extra as well. But first, a word from our great sponsors here at CHGO. Ray Chevrolet in Fox Lake kicking off summer with big savings all month. Go in today to shop their summer sales event and drive home with $10,000 off MSRP on new Chevy models. Check out their selection of over 125 vehicles priced under 20 grand. And one of the area’s largest inventories of Chevys, you’re sure to find the perfect vehicle for you. Plus, Raised Price Promise lets you shop confidently because the price you see is the price you pay. Don’t miss out on their summer sales event going on all month long. For $10,000 off MSRP on new Chevy models, shop Ray Chevrolet in Fox Lake or at ray chevrolet.com. They’ve been serving the community since 1963. Together, let’s drive. I could go for a nice Chevy right now. Yeah, nice one with a little air conditioning right now. It’s been a little muggy out. You know what I could go for? You know what I could go for? We’re doing this what if episode right now. And let me ask you a question. What if you didn’t lose your sunglasses 30 days after you purchase them? Yeah. What if you were like me and you stopped buying $5 pairs of sunglasses cuz you know you’re going to lose them and you look like an idiot and you actually want to get into style. I could have invested the money I I saved. Yeah, exactly. Put it lose them on the roof of your car, lose them at a gas station. We’ve all been there before. And that’s when I found Shady Rays. And people, trust me, it has completely changed the game. These sunglasses are made for real life. Seriously good-looking, polarized, durable, and not stupidly expensive. And here is the wildest part. If you lose or break them even on day one, which I would probably do, Shady Rays will send you a brand new pair. So now I actually can wear my sunglasses stylishly without fear. So here’s what you got to do. We’ve teamed up with Shady Rays to bring you an exclusive offer. Head to shadyrays.com and use code chio for 35% off polarized sunglasses. Try for yourself the shades rated five stars by over 300,000 people. This is what we like to call rank week here at CHO. And we’re all ranking each team is doing it. So if you’re a fan of some of the other teams, the Bulls, the Blackhawks, the Bears, they got a rank week, too, full of whatifs. There’s a guy named Dererick Rose that played in this town. Maybe that will end up in the episode. There are some that are probably uh just as sad as the Cubs. Here we go. But I don’t know if any stack up to exactly what the Cubs are. So, number two on our greatest whatifs in Chicago Cubs history. Number two, what if the Cubs beat the Marlins in 2003? Let it soak in for a second. This one hurts again for me. Not as bad as 84, but it hurts. They had a chance. Tuesday, October 14th, 2003. That’s the game we all know. There’s the popup. Moyes Saloo goes over and Cubs think it’s fan interference. Some poor man, Steve Bartman, is shunned for the Yeah. Just enjoying the game and he gets blamed for the rest of his life. unfair because they still had a chance to win that game. They still had a chance to field the ground ball. They still had a chance to win game seven. So, I don’t know why we even call it what we call it, which I’m not going to call it anymore. What if they beat the Marlins in 03? All I know is after that game in game six, the Cubs actually admitted to us that they booked their flights home. They still had a game to play with Carrie Wood on the mound who hadn’t lost at Wrigley Field in six weeks. And we had two homers in the game in game. We had players on that team booking their flights home. This is mine. You know, 84 is yours. I know. Yeah. 03. This one’s mine. Uh, I’m a freshman in college. Uh, you know how you said your dad didn’t talk for several days afterwards? I didn’t go to class for a week. Sorry, Columbia College. It had nothing to do with baseball, but you didn’t go for a week. Had something to do with physical recovery, mental anguish. Um, what is it? You see those things where you go into the woods and you guttily scream? Uh, that’s what I feel like I did for for a week after this one. Yeah, man. This one’s really tough to take. What if the Cubs beat the Marlins in 2003? I think they beat the Yankees in that World Series. Um, I think they had the horses. I think they had the starting rotation. Again, I always think about everyone focuses on game six. Um, and that inning. I focus in on game seven to be honest with you because Moyes still hits a bomb deep into the night for a two-run bomb. Carrie Wood goes deep. We had that lead and I’ll never forget I was kind of like in uh I was in Lake View and after Carrie Wood hits that bomb I’m like I got to get down to Wrigley as quick as I can and I’ll never it was it was great in 2003 you’re walking and from house to house people are in their front yards back when a lot more people lived around there. But each television was on and from each house I went down Kyle Kyle Farnsworth was blowing the lead each house I walked down further down there. Um, and man, this one this one hurts. 53 and we’re doing this list. You grow up your whole life with trading Lou Brock and the Billy Goat and the Black Cat in 1969 and Leon Durham and Will Clark in 1989 and Carrie would blowing out his arm and and this one for me was just, man, maybe this will never happen. Maybe this isn’t in the cards. Maybe the Cubs will never win the World Series. But I think if they beat the Marlins, I do think they go on to win that World Series in 2003. Listen, the minute Aloo makes the reaction that he makes, I thought to myself, they are cursed. This is never happening and they’re about to collapse. To which they did, so I’m not sure. Then they were down three runs in game seven and Carrie Wood hits that home run and Aloo hits it and you think to yourself, wait a minute, this could still happen, right? You have that hope. But I sort of wonder that even if the Cubs won that series against the Marlins and they came back and they fought through that, if they were so mentally fragile that they let that popup down the left field line then influence a booted ball and then influence guys going to buy their plane tickets home for the next day. If they were that mentally fragile and there was so much weight for all the years of Cubs losing, Cubby occurrences Lou used to call them. Y that they might have had something like that happen against the Yankees anyway. Do they beat Jeter? I don’t know. Yeah. Yeah. Yeah. I don’t know because Jeter wasn’t thinking that way. Jeter wasn’t booking flights. Yeah. My my only my only push back on that one is just that, you know, the Marlins had Josh Beckett in that series who was amazing against the Yankees in that World Series. And I would have I would have gathered and guessed that Carrie Wood and Mark Prior were on the heaters that they were on and they would have been able to put together some some pretty great performances in that. Again, we’ll never know. I mean, the Marlins swept the Yankees. Yeah. I mean, they swept them right out of town. It wasn’t even really that competitive, you know what I mean? When we talk about Jeter and the Dynasty and all that stuff, but no, I think that’s a great point and and it is funny the the mental psych of not just players in series like that, the mental psych that we learn about later on. Yeah. But also the burden that they were under and the weight that that it all started to carry as they got closer and closer and closer. And in the end, we blame a guy with headphones on his head. Not me. I don’t. But people do. But there are plenty of players and moments and situations and lack of execution that uh that made me miss a whole week of school and eat $30 of McDonald’s that night. And so, you know, yeah, it’s a it’s a sad one. That’s my darkest day as a Cubs fan. and all the future Cubs that were on that team. Juan Pierre, Todd Hollinssworth, who put the Marlins ahead for good, Derek Lee. Yeah. Unbelievable. But it’s what makes the 2016 Cubs so remarkable. So, here you go. Biggest whatifs in Chicago Cubs history. If you haven’t figured this one out, you’re not watching Cubs baseball and you’re not a fan. The number one biggest what if in Cubs history. What if it never rained in Cleveland during game seven of the World Series? Obvious shirts has the shirt, right? Yep. What if I told you 17 minutes of rain would wash away 108 years of tears. I’ve got the shirt. I think it’s my favorite obvious shirt. I was there. I don’t know the answer. I don’t know the answer. I watched the champagne go from the by that point I was in the tunnel for the home run. Mhm. I watched the home run on a tiny TV hanging in that Cleveland stadium, not even a flat screen. Hanging down there and I’m sitting there with all the media. We’re watching it. Carrie Wood standing off to the side with his family. The home run and the building starts rocking cuz we’re on a delay. We hear the rocking and we’re like, “Huh? What?” Look up. They wheel all the champagne out of the Cubs clubhouse and all of it into the Cleveland clubhouse. Then the rain delay hits and you’re just you’re not sure what to make of it. I still think that’s it. They’re done. But what makes the 2016 Cubs different than the 2003 Cubs who when they faced the adversity of something silly like a popup down the left field line, the Cubs started booking flights home. The 2016 Cubs went in and listened to Jason Hayward’s speech. It’s the difference, right? I don’t know what happens if it doesn’t rain. Cleveland had all the momentum. There were many times I thought the Cubs are going to blow this and the weight’s going to be too much. And even Joe Madden can’t pull him out of this with his rahrah speeches and the team and all that. Jason Hayward speech. We’re the best team in baseball. We’re the best team in baseball for a reason. Now we’re going to go show it. We’re going to play like the score is nothing. Nothing. You got to stay positive. Fight for your brothers. Stick together and we’re going to win this game. That’s the opposite of booking a flight home. That is the opposite of one 123 Cancun 100%. So I don’t I don’t know what would have happened. My gut feeling is if it doesn’t rain, the Cubs lose the World Series. So I I got to ask you cuz you’re you’re you’re in it. You you were in the tunnel of that game. So from when David Ross hits the home run up to the Rajie Davis home run, is it is it pins and needles? You mentioned the champagne starts rolling in. it start does it start to formulate in your head that I have to get ready for the Cubs World Series? Sort of surreal. My seat is in the right field corner. Yeah. With the media. And I just started I did what I do. I went to the concession stand and I started binge eating. I was eating dogs. I was eating dogs with chili hot dogs with chili and cheese on them. I was just eating. And I’m watching these Cleveland fans just in their sorrow and I’m like, I can’t believe this is happening. This is what I dreamed of covering the Cubs in the world. This is all I ever wanted in TV. And I here I am and right now I think it’s going to happen. The only thing I can do to make it happen is just to eat. And I ate and I ate and I ate. So when I got down there in the tunnel and Rajie Davis hits that home run, I not only felt like I got kicked in the stomach, I had a stomach ache. Yeah. So, it was I thought they were done for. I thought they were done for. And the look on I’ll tell you this, the look on Carrie Wood’s face, he thought they were done for. I don’t want to put words in his mouth. He thought they were done for. But no, it was it was a giant here we go again. I will tell you. So, I I was living um I was living in Los Angeles at the time. I took a one-way ticket and I flew home for the World Series because there’s no way I was going to be in the city that I grew up in and love and not be there. Uh, game seven, I’m at Holiday Club at Irving Park in Sheridan. I convinced my parents who hate coming into the city to come down and watch the game with me. They’re all with me. The Raj Davis home run hits. And honestly, the thing that happened was I stepped outside with my buddy Domini and it’s raining out and I’ll never forget, we looked at each other and it was almost we knew the exact thing and I honestly thought that the Cubs were going to play like a 22 in game. I literally thought it was I couldn’t have taken that cuz I’d have been watching it on this little TV and like I’m covered in plastic wear. I thought it was going to be one of those we’re the sun is going to come up and the Cubs will win the World Series. One of these weird crazy moments and as a fan we kind of locked in and said, “Well, here we go. Let’s do it.” Um I don’t know if the Cubs would have won the World Series if there was a rain delay because I’d never seen him do it before. But God bless that it happened. Amen. That cloud. Oh my god. Partly cloudy skies, scattered thunderstorms. I mean, Tom Skilling, what did you do that night? There was a thought that it was going to rain all night long, right? That was that was a thought. And it was raining in Chicago when the game started, I mean, everyone was waiting outside the bar and it was raining and no one cared. By the time I got out of that clubhouse, I will just tell you that the pictures that I took with people and, you know, we’re we’re just having fun at that point. We got champagne bottles and stuff cuz our work is done. It was still pouring. Yeah. and that field was soaked. So, the crazy thing is even after they come back and win it, like what if they weren’t even able to restart that game? Like there was a window to play the game. What if there wasn’t that window? It was storm. Yep. 17 minutes later, they’re back on the field. They finish it and it unleashes a storm after that for hours. Yeah. I mean, I got one more what if for you because I think about this all the time. This isn’t on the list though, is It’s not on the list, but it’s part of this game though. Is that if if the if the weather doesn’t come in and out the way it does, does it change the wind trajectory? And does KB’s ball go out? Oh, now you’re going deep. Instead of it dying at the track and Albert Mora tags up from first base, does that go out and we win the World Series because CB hits a home run. It’s the It’s the biggest what if it might be the biggest one of the biggest whatifs, if not the biggest in all of baseball history, sports history, because it was the Cubs against Cleveland and all of this drought and these two teams and whoever lost was going to be cursed for the rest of their life. And if you remember 69 and you remember 03 and you remember 84, if it had happened again in game seven after having this lead in 2016, I don’t I think we’re still sitting here and they haven’t won a World Series. Oh my gosh. I really do. Yeah. No, it’s it’s 100% possible. And maybe my final one for you is when they make the movie about the Chicago Cubs and Jason Hayward makes a speech or they make a series out of it and it goes on Netflix, who’s playing Luke Stuckmire? Who do you want? I mean, is Brad Pitt still alive? Yes. This is a what if? Of course. If Brad Pitt still liveswhere, it’s got to be Brad Pitt, you know. Yeah. With the Fight Club abs most likely. Do we have time for anything? Do we have an honorable mention? Can I throw an honorable mention? We don’t have time. What if the Cubs didn’t have lights in 84? What? No. Yeah. The whole 84 lights thing was the reason they played two at home and then three in San Diego is they didn’t have lights. Yeah. So, it would have been a different scenario. Also, the World Series would have been a different scenario. It all would have been crazy. Do you take any uh credence or or currency in them playing the day games and I don’t know. Yeah. Yeah. Yeah. I don’t know. I don’t know. I that that’s easily the best one. What if Theo turns down the job at Starbucks? O. Oh my gosh. Well, we’re sort of living that scenario right now. Then we’re overpaying for Mike Rizzo in 2013, 2014 or Dave Dumbrossski or I don’t know. Yeah, I don’t know. I guess we’ll never know. But the Theo one’s a good one. What if he goes to What if he goes to Starbucks, they get his order wrong and he’s like, “Ah, I’m out of here.” Which has never happened before. Kid at Starbucks writes the wrong name. They write Jed on it instead and he’s like, “What? I’m not Jed.” Thor Epstein. It’s not It’s not meant to be. I’m going back to Boston. I don’t like to think about that one. Now, that’s a ridiculous one. Keeps me up at night. But the rain one still keeps me up at night. I still have a stomach ache every time I think about it. Oh, it’s one of the best nights. It was a great night. I ran to Grace and I got stopped by people on horses cuz no one was getting I hope they were police. They were police. Oh, okay. Otherwise, it was just people riding random pour a shot from a second floor apartment and I tried to You know what I mean? Because who cares? All right, thanks for checking out the uh CHGO Cubs podcast. Rank Week, the biggest what-ifs in Cubs history. Don’t forget, we’ve got one for each of our teams. So, make sure you check out the one from our Bulls guys, Blackhawks, Bears, White Socks. We got a lot of whatifs in this city and you’re about to hear about them like the mayor.
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What if the Cubs never traded Kris Bryant or Anthony Rizzo? What if Sammy Sosa stayed a Cub — or Alex Gonzalez made the play in 2003? In this episode of the CHGO Cubs Podcast, we rank the Top 10 biggest “What Ifs” in Chicago Cubs history — from the collapse of the 1969 Cubs to moments that nearly derailed (or could’ve extended) the 2016 championship run. These are the franchise-altering twists that could have changed everything at Wrigley Field.
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