Quite simply, a bank would have done a risk analysis and quickly pushed for a settlement, whereas Thiel was motivate by hatred, and the kind of entitlement which comes from power and wealth. He was to happy to carry all the risk and let Hogan reap the rewards give the reward to Hulk out of pure hatred for Nick Denton. Decision makers at banks always report to somebody. Thiel knows that being a billionaire means that he doesn't have to justify his actions to anybody.