He's not required to take the first gig.
But he is required to search and find a job in "good faith." There's a bunch of case law in Indiana (and other states, but Indiana law applies to this contract) about what constitutes good faith. In short, Crean has to genuinely search for a job that isn't below his own market value.
A key element of this, though, is that IU pays the buyout monthly through June 30. 2020, and all of Crean's earnings in that time period are credited against the buyout. He must report all earnings to IU, and IU will deduct them from future payments. At the end of the contract period (i.e., on July 1, 2020), they will take an accounting, and if Crean's earnings PLUS what IU has paid him add up to more than the buyout, Crean has to return the difference to IU.
So, if he sits around for a year and collects money from IU, there is a chance he is collecting money he will one day have to return.
All of this, of course, simply points back to what a lot of people have been saying: if a divorce happens, it is in the best interests of all parties to agree to terms, and avoid five years worth of potential litigation over this stuff.
goat