I think 100% Jerry sells. This is a man staring at his power diminishing. What is this info we are going off of? 1983, 2008, ptthp. He's 86 now.
2005 was the height of his powers. He brought a team to the world series with his preferred way of team building. Not overpaying for stars, not giving a bunch of money to young players that weren't yet productive. His team gettin ga world series while the 200 million yankees didn't. He ebbed to his white sox team building for the bulls, bringing back a former player to focus on getting college stars and no more high school guys, and voila, suddenly in the playoffs.
By 2012, he had essentially won all CBA things he has fought for. So much of team building largely has fixed costs, INTL: Draft, there is a real luxury cap ceiling.
Jerry was no longer a power broker in the latest CBA. He couldn't fight to keep steve cohen out. His basketball team withered to mediocrity with his team building style, finally accepting a resignation from Paxson and ceding all power to his son.
Now with the sox, he accepts a rebuild. The team is a winner, what's his last wish? To see TLR lead his team to a World Series. The best manager he's ever seen.
TLR is absolute garbage, widely ridiculed and panned, team underachieving. Another L for Reinsdorf.
Selling the team would give one last area where Reinsdorf can feel powerful and in control. He has uber leverage, he can wheel and deal to get a maximal return. It will be his last stand.
I don't think he gives up that last bit of fun to an estate lawyer. Especially with the chance to look at some other new-money finance billionaire in the eye and tell him to kick sand.