He never understood it. He didn't want to pay MJ and famously said he would probably regret those deals. JR is all about maximizing his and investors pockets. Stupidly not realizing that if you spend money, you can truly make a ton more.
The fact that JR is finding out that Chicago is not going to bend over backwards on the new stadium is why I believe JR will sell the team. He is going to let the new owner fight the battle.