If you think the bailout compares to a "loan", I can see why you find the analogy inapt. I would compare the requisite bailout magnitude to paying off your friend's mortgage, his friend's mortgages, and their student loan debt... In which case, send me those passwords.

Like most "loans" to friends, this one isn't being paid back, no. "Loan" is the word friends use for gifts to try and make it more palatable, but if you're charging interest and expecting prompt repayment they aren't your friend, and if you aren't it's not a loan.

But:

Either give him the money or tell him to fuck off. Those are the only realistic options. If you think he's going to spend it on drugs and he's sitting there promising that no, he'll use it to cover his rent, honest, and you don't believe him then don't give him the money. There's no moral option where you say yes, then lock him in your basement; believe it or not that's actually quite illegal.