I feel the McCaskey family are honestly trying to win, and they are unwilling to change with the modern NFL. Plus they are just not very good at picking the people to trust (Accorsi). .
the shoopster agrees with you, Md. He believes George especially is genuine in his desire to turn the Bears into winners FOR THE FANS. There's a good reason why he christened him the complimentary "King" George (in contrast to the also apropos "Curious (Looking)" George, which was also in the running for his sobriquet). George may be the only McCaskey who really wants to see the Bears win not for the money, but simply for the joy of winning.
Contrast this with Michael, who wanted the Bears to win for vanity reasons. Desperate to wrestle the legacy of the franchise away from Mike Ditka, who was BECOMING the Bears (hell, Ditka was so symbolic of the franchise that national broadcasters on Monday Night Football once seriously discussed their observation that Ditka and the Bear in the Bear logo had the same facial structure), Michael sought to claim the franchise not only from Ditka but also Halas by firing Ditka (Halas's last handpicked Head Coach) and splitting General Manager duties with Dave Wannstedt in order to rebuild the Bears - he hoped - as Jerry Jones later built the Cowboys, a prescient bit of ego-mongering by Michael in which he sought to encourage the attention and adulation befitting an NFL vision if not visionary in much the same way Jones has. It had nothing to do with winning and everything to do with Michael McCaskey.
George isn't that guy. He just wants to yell down from the press box as a Bear receiver breaks away for a touchdown, or a defensive end swoops in for a crucial sack. He loves the game.
And the recent reports about how he spent nearly two straight days in the hospital with Zack Miller after his gruesome knee injury shows his character. Above all, he's a good man. There's a lot to like about the guy.
Perhaps it's that good nature, that innocence and belief and faith in what's good, that leads him to put his trust in men like Accorsi and Ted Phillips, lifelong users who prey on soft-hearted fools like the Kingster for their own egomaniacal and financial gain. He just can't imagine someone like Phillips prioritizing a need for personal accolades over the joy of a successful football team. To George, the Sweatster's belief that if he can't succeed, all around him must fail makes so little sense, he can't even be on guard to recognize it when it's happening right in front of him
"Uncle" Ernie Accorsi is the worst of the evils a man like the Kingster must guard against, a mercenary who waits yearly for teams and owners in dire straits to come calling on his "expertise" so he can shoehorn undeserving associates like John Fox into multi-million dollar pay days. The recent reports that Accorsi may have sold the woebegone New York Giants on hiring has-been Fox as their Head Coach after he's presided over a 14-and-34 three-year debacle with the Bears elicits first chuckles, then outrage over Accorsi's hubris. There oughta be a law against what this guy does, and did to the Bears.
In the end, though, George has to be be held responsible for refusing to put his child-like indulgence in the joy of the game in proper perspective in order to protect the Bears from the abuses of such vultures. He's a nice guy who's thus far a disaster as a football executive.
Oh, and one more thing - he's a mama's boy. It's Virginia who insists on keeping Phillips around and indulging him like a smaller, swarthier son in return for "Sweaty" Teddy extricating Michael and the family from a very embarrassing situation with the Soldier Field renovation in the late-nineties. George needs to stand up to her, too, instead of putting importance and emphasis on reporting "Virginia's pissed" at pressers, as if somebody's supposed to care. The fact that he does calls into question his makeup as the right guy for the job at hand.