[Carl] …biggest sleeper pick to breakout long term is George McCaskey.
July 30, 2025
[Carl] …biggest sleeper pick to breakout long term is George McCaskey.
26 comments
Can’t wait to see George get his flowers one day ✨
One time I was in an elevator at Soldier Field as a kid making fun of the Bears ownership, and George McCaskey was right behind me.
He did not say anything. Neither did my dad.
When I was younger, I was lucky to see a bears training camp and Mr. MCcaskey showed up and started chatting up everyone in line, riding his bicycle.
He was extremely nice and easy to talk to. I thought he was just a nice fan. Only later did I learn he was chairman for the bears.
I hope the bears future is great.
“Barstoolcarl” who hasn’t worked at barstool in months – maybe over a year? Lol
You can say a lot of things but you can’t say he doesn’t care.
My friend was on a flight with him and he was willing to speak with him about his concerns about the bears and the franchise in general. Didn’t get defensive. Heard him out. Chatted for about 20 mins. And was genuinely a great guy.
You could definitely do WAY worse for an owner, and it’s not that they don’t care about winning like others (Reinsdorf), they’re just pretty clueless about how to get it right. But I’m feeling optimistic they finally did this go round
As a fan of the White Sox and Bulls, it always annoyed me how much vitriol I’d hear about Bears ownership when Reinsdorf is an all time terrible, cheap, selfish owner in sports history. We’re talking Marge Schott territory.
Met George at the bears draft party a few years back. He was casually walking around the crowd and let us get a picture with him and chat a bit. Nice guy and I do feel like he cares about the team more than people give him credit.
I’m sure he’s nice and all even if I put aside the kind of weird vibes walking past him at training camp back in the day. I’ll give him credit for always being around the fans.
But I cannot think of many positives over his time in that position. The dude was handed that shit and has a laundry list of failures.
Jerry Reinsdorf is the scum of the earth and deserves to rot. I can’t say the same for George. He may be (boarder line incredibly) incompetent, and is the definition of nepotism. But he seems like a nice dude.
There. I did it. I said the nicest thing I could possibly say about him. And people said it couldn’t be done.
This man is why I will never have the moral dilemma of rooting for a bears team that employs deplorable human beings, like desaun watson or tyreek hill. I appreciate that
I saw him at training camp last week. He lives up to his reputation. He was there from when it started to when we left. It’s kinda wild how he greeted everyone and took any comments on the chin.
He,as a person, was never in question, it was his meddling in football operations that fans were upset about.
George McCaskey redemption arc would be sweet, and I’m rooting for the guy.
#BELIEVE
Yep
Great guy. Sell the team.
My guy Risabh!
The only complaint about George is his incompetence about picking gms/HCs. In terms of nfl owner could be a lot worse (Spanos or Snyder for example). My sleeper breakout pick this year is Kmet. 1K yards 10 TDS
I mean it is kind of an asshole move to raise prices 15-22% every season after the dumpster fire seasons we’ve seen lately. I mean where do they get off asking for 20% or more when the fans were chanting “sell the team” at the Seahawks game last season.
My prediction is that in 5 months everyone will be saying that he should be fired/the McCaskeys need to sell the team.
I’m sure George is a wonderful guy. I’d love to be a fan of his, but up until possibly now, he’s put a shit product on the field and has seemingly meddled in football operations.
Time will tell – if we start winning and George stays in his fucking lane, I will feel better about him. Currently, I’m still sour over the last decade of shit decisions.
He was out greeting fans for the majority of training camp today. No security just a girl that had staff written on her back. He would talk about anything you wanted.
George is a good dude. They just run the organization *too* much like a family.
Brought my 9 year old to his first game last year. We were throwing a football around in the lot and who came walking through?? George. He walked over to me and asked if he could give the kid something so I said sure. He handed my son a pack of Bears playing cards. It was a small gesture but it was the highlight of his day. He still has the glossy Keenan Allen card from that pack and talks about the time he met the Bears owner. I’ve complained about the owners plenty over the years, but he seems like a genuine guy and I’m here for the redemption arc!!!
Cue the music
Do do do do
Inspector gadget
The bears failures of last season certainly fall onto Poles, not the McCaskeys.
![[Carl] ...biggest sleeper pick to breakout long term is George McCaskey.](https://www.rawchili.com/wp-content/uploads/2025/07/cn3tponjcxff1-1080x1024.png)
26 comments
Can’t wait to see George get his flowers one day ✨
One time I was in an elevator at Soldier Field as a kid making fun of the Bears ownership, and George McCaskey was right behind me.
He did not say anything. Neither did my dad.
When I was younger, I was lucky to see a bears training camp and Mr. MCcaskey showed up and started chatting up everyone in line, riding his bicycle.
He was extremely nice and easy to talk to. I thought he was just a nice fan. Only later did I learn he was chairman for the bears.
I hope the bears future is great.
“Barstoolcarl” who hasn’t worked at barstool in months – maybe over a year? Lol
You can say a lot of things but you can’t say he doesn’t care.
My friend was on a flight with him and he was willing to speak with him about his concerns about the bears and the franchise in general. Didn’t get defensive. Heard him out. Chatted for about 20 mins. And was genuinely a great guy.
You could definitely do WAY worse for an owner, and it’s not that they don’t care about winning like others (Reinsdorf), they’re just pretty clueless about how to get it right. But I’m feeling optimistic they finally did this go round
As a fan of the White Sox and Bulls, it always annoyed me how much vitriol I’d hear about Bears ownership when Reinsdorf is an all time terrible, cheap, selfish owner in sports history. We’re talking Marge Schott territory.
Met George at the bears draft party a few years back. He was casually walking around the crowd and let us get a picture with him and chat a bit. Nice guy and I do feel like he cares about the team more than people give him credit.
I’m sure he’s nice and all even if I put aside the kind of weird vibes walking past him at training camp back in the day. I’ll give him credit for always being around the fans.
But I cannot think of many positives over his time in that position. The dude was handed that shit and has a laundry list of failures.
Jerry Reinsdorf is the scum of the earth and deserves to rot. I can’t say the same for George. He may be (boarder line incredibly) incompetent, and is the definition of nepotism. But he seems like a nice dude.
There. I did it. I said the nicest thing I could possibly say about him. And people said it couldn’t be done.
This man is why I will never have the moral dilemma of rooting for a bears team that employs deplorable human beings, like desaun watson or tyreek hill. I appreciate that
I saw him at training camp last week. He lives up to his reputation. He was there from when it started to when we left. It’s kinda wild how he greeted everyone and took any comments on the chin.
He,as a person, was never in question, it was his meddling in football operations that fans were upset about.
George McCaskey redemption arc would be sweet, and I’m rooting for the guy.
#BELIEVE
Yep
Great guy. Sell the team.
My guy Risabh!
The only complaint about George is his incompetence about picking gms/HCs. In terms of nfl owner could be a lot worse (Spanos or Snyder for example). My sleeper breakout pick this year is Kmet. 1K yards 10 TDS
I mean it is kind of an asshole move to raise prices 15-22% every season after the dumpster fire seasons we’ve seen lately. I mean where do they get off asking for 20% or more when the fans were chanting “sell the team” at the Seahawks game last season.
My prediction is that in 5 months everyone will be saying that he should be fired/the McCaskeys need to sell the team.
I’m sure George is a wonderful guy. I’d love to be a fan of his, but up until possibly now, he’s put a shit product on the field and has seemingly meddled in football operations.
Time will tell – if we start winning and George stays in his fucking lane, I will feel better about him. Currently, I’m still sour over the last decade of shit decisions.
Well that’s a take. How’s his route running?
https://preview.redd.it/3oa8bj9zwxff1.jpeg?width=3072&format=pjpg&auto=webp&s=350dc7be3231711fd79d9fe6f71ba0778b2b6732
He was out greeting fans for the majority of training camp today. No security just a girl that had staff written on her back. He would talk about anything you wanted.
George is a good dude. They just run the organization *too* much like a family.
Brought my 9 year old to his first game last year. We were throwing a football around in the lot and who came walking through?? George. He walked over to me and asked if he could give the kid something so I said sure. He handed my son a pack of Bears playing cards. It was a small gesture but it was the highlight of his day. He still has the glossy Keenan Allen card from that pack and talks about the time he met the Bears owner. I’ve complained about the owners plenty over the years, but he seems like a genuine guy and I’m here for the redemption arc!!!
Cue the music
Do do do do
Inspector gadget
The bears failures of last season certainly fall onto Poles, not the McCaskeys.