Sunday, November 30, 2025

George McCaskey Savagely Burned Eagles Fan On Flight To Philadelphia

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Chicago Bears fans know George McCaskey well by this point. He is now the principal owner of the franchise following the death of his mother, Virginia. His reputation is that of a well-meaning family man who tries to do right by the franchise but has a tendency to make poor decisions. The past decade provides a wealth of evidence to support this. Chicago has endure four head coach and three GM changes since he took over in 2011. The Bears just achieved their third winning record in that span on Friday.

Fans have a complicated relationship with McCaskey. Still, he’s never come across as anything but determined to make the fan experience great. That approach has made it easy to overlook the somewhat cheekier side. McCaskey isn’t known for outlandish quotes, but it appears he finds a way to let fans of opposing teams have it when the situation arises. Apparently, the Bears’ owner got into a bit of a debate on a flight to Philadelphia with an Eagles fan and her husband.

McCaskey gave her a souvenir.

George McCaskey is a master of the subtle burns.

Calling somebody delusional or stupid is all fine and good. For some reason, little digs like that sting even more. If nothing else, you have to love George McCaskey being a good sport about it. Most owners wouldn’t even bother riding in the same plane with fans. They’d just have their own private plane. McCaskey is a man of the people. No owner is more involved with folks on the ground than he is. He regularly walks through tailgates, greeting fans and speaking to them. His charity work is highly-regarded. Say what you want about his football decisions, you can’t say he’s not committed.

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This was a rare moment for him to have some fun. The Bears have been bad for a long time. Now that they’re good, he was able to puff out his chest a little bit. It didn’t look like a bad move either, as his team went on to crush the Eagles 24-15 later that day.

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Krisanthony
Krisanthony
Nov 30, 2025 9:05 pm

@jmscooby. Ok, I respect that. But let’s not forget that it took 7 years even with Roseman. It was also a type of move the “old Bears” would never have made. Hiring a 35 yo GM. The only thing they knew was hiring a head hunting firm to show them that they should hire who they already employed before (Jerry Angelo) They were also an organization with no connections to the rest of the league outside of their family friends in New Your Giants family and the Rooney family in Pittsburgh. I would guess they didn’t know who Roseman was… Read more »

jmscooby
Nov 30, 2025 1:20 pm

@Krisanthony Like I said, I liked what Philly’s front office was doing as far as adding talented players, so I went through their front office looking at the young candidates to bring over to Chicago, and Howie happened to be the guy. Then he got the Eagles gig, then lost power to Chip Kelly briefly. I do give Andy Reid a lot of credit because I think he prioritizes the CB position the way it should be. I also think if we had a coach like Ben J., we could have won a SB with Rex. He needed someone to… Read more »

katherinne
katherinne
Nov 30, 2025 1:06 pm

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Krisanthony
Krisanthony
Nov 30, 2025 12:42 pm

@jmscooby, in 2010 you wanted the Eagles EVP? How did you know about him and what part of his work as Andy Reid’s 2nd stood out to you? Not questioning your claim but what of Rosemans one year as the EVP stood out? Andy Reid was the GM and that was taken away from him in a very public way in 2010 when they promoted Roseman to take over. Would the Bears even have had the chance based on the timeline? Looking at Eagles first 7 seasons under Roseman, they had a 56-56 record. Then we know how successful they’ve… Read more »

Last edited 8 hours ago by Krisanthony
jmscooby
Nov 30, 2025 4:39 am

George seems like a nice enough guy, and it’s nice to see him show a sense of pride in the team instead of considering it a Ted Phillips run business. With major decisions made by former Colts head honchos. I do blame ownership complacency on our team being a cesspool for the last 2+ decades. I’ve said it before, but I wanted to fire Angelo 3 years earlier and hire Howie Roseman away from Philly when he was a VP. The Eagles are just one of those teams that has it together and know what they want to do, unlike… Read more »

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