The AIG bailout (now up to about $182 billion) is the perfect case of what should never have happened.
AIG was essentially two companies under one roof: a giant boring insurance company that was quite solvent and a giant speculative hedge fund that lost hundreds of billions. The two should never have been allowed to coexist (we regulate insurance companies to make sure they don't blow all the premiums they're paid on stupid gambles) and once AIG became insolvent it was not necessary to bail out the hedge fund operation to keep the insurer going.
Being the biggest insurance company in the world, AIG collapsing would likely have caused a mass panic and set off a bad chain of events. The collapse of the hedge fund which made giant bets with other hedge funds and financial entities wouldn't have done so. It would have screwed over the fund's counterparties (a "counterparty" in this instance being who the hedge fund was making bets with), but it wouldn't have caused a massive chain reaction.
A lot of this is due to the kind of bets AIG's hedge fund was making. In many instances, it was taking relatively small amounts of money on the chance that very very large CDOs (collateralized debt obligations, the massive bundles of mortgages that set of the entire debt crisis) would stop paying off. In some cases this was billed as "insuring" the CDOs, but they were pretty much straight up bets since the people buying the "insurance" weren't the owners of those CDOs, they were just betting on them failing (kind of like taking out fire insurance on someone else's property then cheering for the arsonists).
Being willing to take these giant bets with a huge downside was mostly due to the way the hedge fund people were compensated. If they made a risky bet that was calculated to make money over an extended period of time (like taking huge bets on the health of poorly understood CDOs),
the hedge fund people got paid for the entire estimated profit right away. They didn't have to wait until the deal had run its course. They didn't even have to wait until the deal had made any money at all. They got paid right away. This obviously created a massive conflict of interest, giving the hedge fund guys
incentive to make any deal they could "estimate" would make money regardless of the risk.
When the CDOs started going under and AIG suddenly didn't have the money to pay off their bets; the Federal government didn't need to step in and start shoveling money into the furnace. The could have forced AIG into chapter 11, fired all the management, then spun off the giant insurance company we'd decided was essential to the global economy. The insolvent hedge fund could then have been wound down.
There would not have been enough money to pay off all the bets AIG had lost, but so what? It's not the taxpayers' responsibility to bail out every company that makes bad bets and goes under. And, as stated, in many cases the counterparties had only paid out relatively small amounts of money getting some truly sick odds on their bets (up to 100:1). However, between the money they did have, the bets they'd made that didn't actually lose, and any money they could've clawed back from what was paid to hedge fund guys based on phantom profits;
there likely would have been enough to pay back the money the counterparties had put up to make those bets. The counterparties wouldn't have been happy, but that's what happens when you make giants bets with a company that'll never be able to pay them off if they lose.
So, in the end, no one would have been out of pocket any money and the incompetents running AIG would have been out on the streets.
Instead, we spent billions bailing out not the insurance side (which was not insolvent) but the hedge fund side which never should have been bailed out.