By the way, I've heard this idea that you ask Phillips to step down as Team President, but keep him on as your main money man. That doesn't work.
I'm reminded of a story that was told by Adam Hoge and Adam Jahns on their Athletic podcast.
In 2001, the Bears had identified a guy coming out of college that they knew beyond a shadow of a doubt was going to be an amazing NFL player, possibly a Hall of Famer. This was back before salaries for draftees were slotted. You just signed your guy to however much money you agreed on, so high draft picks made A LOT of money (Sam Bradford was the last such guy).
Mark Hatley went to Ted Phillips and asked for the money to sign this player so that Hatley could trade up in the draft and get him. Hatley knew he could get a deal done to move up, but wanted to make sure the Bears brass were willing to pony up the money.
Phillips said no, it was just too much money. The Bears stood pat at #8 and drafted David Terrell.
The guy they were after went #5 to the Chargers, was a consummate All-Pro, and made the Hall of Fame.
That guy was LaDanian Tomlinson.
All because Teddy didn't want to put aside the cash.
Don't you think the Bears would've made some major bank if they had LaDanian Tomlinson in the backfield deking out defenders week after week at Soldier?
There are plenty of other stories like this.
This is the danger of keeping Phillips on as the money man.
Point being, no, don't be the Bulls, who keep shitty people around because they have a personal relationship with the brass, or brass doesn't have the balls to kick them to the curb. Sever the relationship, cut out the cancer. That may also include the McCaskeys, although I'd settle for starting with Phillips.