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.