We have to assume both sides are rational and pursue a strategy that yields the most $.
UConn: Not offering a settlement because they had cause to terminate (this has now been PROVEN) and they think they'll win arbitration and they think the odds + costs of losing a lawsuit are less than any viable settlement
Ollie: Here the calculus is rougher, he pursues lawsuits at no cost and that discipline is leading to legal strategies taxing the other side, pursuing throw ___ on a wall. Add the burden of Ollie's divorce settlement creating a deficit hole that only his old contract could have supported.
Ollie's choices & litigation indicate that Ollie knows the expected value of winning a portion of salary are greater than the ongoing damage he does to his reputation and hire-ability. The double edged sword of this is that means it is very likely the poor performance, violations and cause are so bad that he isn't getting a job anyway so he might as well burn every bridge to get any possible portion of his now long gone salary.
The situation is Ollie recognizes his poor performance means he'll never coach again, so there is nothing to lose by slinging mud. It is unfortunately indicative of how very bad he was at his job that his best chance of getting any future money from coaching is any and all litigation against his former employer.
Someone with nothing to lose can be dangerous, but UConn also has known this from the get-go and still pursues a no settlement strategy.
I think KO's optimization strategy would have been to portray himself as a good guy who got caught up in confusing NCAA rules. UConn likely would have written something in support of that, but stressed that compliance is important. His representation's scorched earth campaign was a tactical mistake in that:
1) It failed to get a desirable result for Kevin;
2) It severely damaged KO's public reputation among UConn fans;
3) It burned bridges with people who could have and would have helped him;
4) It will give employers pause in hiring him; and
5) It poisoned the negotiation well making a negotiated settlement unlikely.
As I've said handling the high profile client is different from handling a regular case. It seems as if his representation didn't grasp that. Of course it's possible that they did and KO instructed them them to pursue their scorched earth strategy.
I have a quibble or two in how UConn's representation handled this case but by and large they have made the right decisions and look to be about to prevail. There is a natural tendency to mistake false equivalency as being fair minded. "Well they are both at fault" sounds measured but isn't automatically correct. This is one of the times that it isn't.