LAS VEGAS — Back in December of 2011, the Cincinnati Reds pushed their chips in for the following season. To land a frontline piece, the Reds dealt three future All-Stars (Yonder Alonso, Yasmani Grandal and Brad Boxberger, plus durable starter Edinson Volquez) for starting pitcher Mat Latos.
The 2012 Reds became the organization’s best team of the last 25 years. Latos posted a WAR of 3.4 in that season, made 33 regular season starts and was a key part of the Reds’ playoff rotation. That season ended when the Reds blew a two-game lead in the first round of the playoffs against the Giants. The following year, the Reds lost the NL Wild Card Game to the Pirates.
Then between 2014 and 2019, the Reds were bad. They needed impact young players like the ones that they traded away for Latos, and they didn’t have them. Was the Latos trade worth it? There’s no right answer. It’s a matter of opinion, and you’ll hear different ones around baseball.
Fifteen years later, the Reds have another young team that looks ready to take the next step. Heading into 2012, the Reds had Joey Votto, Jay Bruce, Brandon Phillips, Johnny Cueto and Homer Bailey. Now, the Reds have a strong young core that includes Elly De La Cruz, Hunter Greene, Andrew Abbott, Matt McLain, Spencer Steer and several others.
Is it time for the Reds to push their chips in? Is it time for them to make another deal like the Latos move where they trade their top prospects for an impact piece that would elevate the 2026 Reds? Or is the long-term value of those players too important to the sustainability of the organization, and would trading some of those players risk another half-decade of irrelevance down the road like the one the Reds faced between 2014 and 2019?
In reality, you never really know when it’s the right time for the big move. It’s a leap of faith. Survey 30 GMs about when it’s time to go all-in, and you’ll get 30 answers on how and when you should go for it.
“Some of it just depends on your objectives,” said Cardinals GM Chaim Bloom, who previously ran the Red Sox front office. “You may want to do this steadier to where you’re giving yourself a lot of bites at the apple. You may decide to push. It’s so individual to the organization and all the way up to ownership and the preferred style for that organization.”
Every organization is different. Because of the payrolls that teams like the Dodgers, Mets and Yankees have, they can afford to be aggressive every year. They can outspend their mistakes.
“It comes down to your feelings and trusting your feelings,” said Phillies GM Dave Dombrowski, who has also run the Red Sox, Tigers, Marlins and Expos. “That’s what I’ve always done. It’s important that you’re realistic with yourself. When it comes down to the nitty-gritty and there are all types of opinions and thought processes and suggestions, you listen to all of them and it’s important. First and foremost, you have to be realistic with yourself for the good of the organization. Realistically, do we have an opportunity or too many question marks to do so?”
Asking GMs around the league, the role of ownership consistently comes up in this conversation.
“Some of that is the desire of the organization (to make a big move),” Cubs GM Jed Hoyer said. “When you do that, by definition, you’re leaving yourself exposed to the future. There’s no full-proof way. You can’t leverage the present without exposing the future. A lot of it comes down to the desires of ownership and if that’s what they want.”
Some teams are more comfortable pushing as many chips as they can in on their big league club and leaving themselves more vulnerable down the road.
Dombrowski ran the Tigers from 2002-2015, and Detroit operated as one of those teams.
“I would not publicly have said this at the time, but we (the Tigers) were investing a lot more in our current players and not worrying as much about the future,” Dombrowski said. “You knew at some point this was going to be trouble. That was more an organizational philosophy of where are you going to spend dollars. It starts with ownership on down.”
Between 2015 and 2023, the Tigers finished seasons with 74 wins, 86 wins, 64 wins, 64 wins, 47 wins, 23 wins (64 wins in the COVID shortened 2020 season), 77 wins, 66 wins and 78 wins. The Tigers overhauled their baseball operations leadership heading into 2023, and now they’re back on the right track with a more sustainable model.
Now with the Phillies, Dombrowski and Philadelphia’s ownership have a different philosophy.
“With our club (the Phillies), I’ve heard our window is closing,” Dombrowski said. “Well, we’ve won more games over the last four years and been in the playoffs four years in a row. I don’t think all of the same players are going to be back with us because we just can’t afford to bring them all back and there are some other guys who are free agents. But by bringing in young players and supplementing, you can keep your window of the organization open. I look at it two different ways. There’s that group (of older players), but the window of the organization might be larger.”
The Brewers, the best small market team in baseball in the 2020s, consistently disappoint their fans with the moves they make. They haven’t executed that big all-in trade. They’ve even dealt cornerstone pieces like Corbin Burnes, Josh Hader and Devin Williams. Ace Freddy Peralta is a hot name in trade rumors this winter even after the Brewers had the best record in baseball last season.
Brewers GM Matt Arnold has had to make unpopular decisions. Most of them have worked, and the Brewers keep winning.
“If you haven’t made a bad trade, you haven’t made enough trades,” Arnold said. “We’re certainly going to make mistakes on those. At the same time, we’ve had success with trades as well. Those are tough. Any time you’re taking away value from your Major League team, that’s going to sting. You have to be ready for the next man up.”
The Brewers have made the playoffs in seven of the last eight years, and they’ve reinvented themselves several times along the course of that run.
“There are horizons to that and things we need to keep in mind when we’re acquiring players, but our focus throughout the season is win the game tonight,” Arnold said. “We spend a lot of minutes on scouting and player development. That’s a huge part of it. Our coaches at the big league level get the most out of our players. It’s a great team effort. Our ownership supports us in a way that we don’t have to operate like the smallest market in the league, which we are. We get great support from ownership. We work our tails off internationally to sign good players there. We work really hard in the draft. It’s a great team effort.”
On the other side of the coin is Hoyer and the Cubs. Heading into 2025, they executed one of the most aggressive trades in MLB when they dealt a top prospect plus their third baseman for a star in Kyle Tucker who was on an expiring contract. With Tucker, the 2025 Cubs won 92 games as well as the Wild Card Round series before losing to the Brewers in the next round.
This winter, the Cubs will likely be in the market to make another splash.
“If you’re set up for the long run, you might want to go for sustained success,” Hoyer said. “If you feel like contractually you have a reason that now is the moment, that makes sense if your best players are coming off the books or whatever. All of those things factor in.”
He said that while there are times to really push your chips in, there are different levels of aggression.
“It doesn’t have to be throwing your watch and keys on the table,” Hoyer said. “There are ways to do it. But there are seasons you’re more likely to win than others. Sometimes you want to maximize your chances in a given year.”
Diamondbacks GM Mike Hazen runs a team that played in the World Series in 2023 won 89 games in 2024 but took a step back in 2025. They were sellers at the deadline last July. Now, Hazen is looking to get the Diamondbacks back into contention in the NL West.
“I’d like to (push my chips in) every year if I had the opportunity to do it,” Hazen said. “Being competitive is one of the most important things we can do. Knowing when to actually push your chips in, it’s more about what’s the answer. What does that mean? Trading all of your prospects? Maxing out your payroll? I don’t really know what pushing all of your chips in really means. We try to be as competitive as possible every single year.”
As you can see, every GM has a different answer.
There’s one thing that they all seem to agree on.
You have to have the right pulse of your team.
“No. 1, you have to really take an unemotional look at your roster and your organization and make sure there’s enough objective markers and make sure you’re not deluding yourself in terms of your readiness for that,” Bloom said. “Then there’s a bit of a feel for when it’s time to push. And, how you do that. There are a lot of different ways you can do that. The most important part is to understand where you are and act accordingly. The worst things happen with organization planning when you behave in a way that’s not reflective of where you actually are. That’s when you really get off course.”
2025 WXIX