I think the thing is that he knows this is the beginning of many more seizures for him. Much like Lehman failing triggered a huge chain of events (to take the guy's own analogies).
So for him, he's looking to save his business. Doesn't mean we should bail the guy out, but the situation might be much graver than that 87 number might imply.
Yep. I suspect he is way over-leveraged, and losing the income stream from those 87 medallions will prevent him from servicing the debt on his other medallion loans. Could set off a chain reaction that wipes out everything he has (not that this means we should bail him out).
You, a billionaire, own 1000+ medallions, and you can't pay for 87 more because you can't secure the money?
You made an investment, and it failed. Time to move on.