Today, it's increasingly likely Obama might have to make an eerily similar decision, with his administration apparently priming for some kind of action in Syria.
This time, though, would be different. The airstrikes would not be against the Syrian government, but rather against Islamist militants. The Islamic State militants (a.k.a. ISIS or ISIL) are the ones who murdered American journalist James Foley on video last week and have taken over significant portions of both Syria and neighboring Iraq.
The White House said its actions in Iraq were taken under Obama's authority as commander in chief rather than under the use-of-force resolution passed more than a decade ago for Iraq. So it's not clear whether it would again seek congressional approval for military force in Syria.
But some members are calling for Obama to do just that. They include Sen. Tim Kaine (D-Va.), who said Monday that "I do not believe that our expanded military operations against ISIL (another name for ISIS) are covered under existing authorizations from Congress." Translation: Get that use-of-force resolution before you do anything else.
But would Congress deliver it? And, more broadly, would the American people sign off on the decision, whether made with or without the approval of Congress?
Certainly, Obama's call for airstrikes last year was not met with approval; that much was abundantly clear. And it wasn't just from Congress; a Washington Post-ABC News poll at the time showed Americans opposed the airstrikes 64-30.
But now, the opposition is a terrorist group that Defense Secretary Chuck Hagel labels "beyond anything that we've seen" in terms of its wherewithal, and things could certainly change. In addition, the administration's airstrikes in Iraq have proven popular, with a Washington Post-ABC News poll showing Americans approved of them 54-39 (and other polls showing even more support).
But that was in Iraq -- a country in which Americans sacrificed thousands of lives and trillions of dollars over the past decade. Support was undoubtedly buoyed by that investment and the fear of losing hard-fought gains in that country.
In Syria, there is no such long-term investment. So basically, it comes down to whether Americans see ISIS as something worth stomping out.
The Syrian conflict isn't the only one in which Americans have been resistant to get involved. The American public has basically opposed every potential military action in recent years except the Iraq airstrikes. Without an obvious American interest in any of these conflicts -- whether in Egypt, Libya or Ukraine -- public opinion has resolutely stood in opposition to involvement.
Things could be different in Syria. After all, ISIS is the same group that's in Iraq and was just on video murdering an American journalist. Its reputation for brutality could also make it a more attractive target than was the Syrian government, which we're guessing Americans didn't see as a real direct threat to the United States homeland.
For now, it would make logical sense that support for airstrikes in Syria would be somewhere between where it was last time (30 percent) and where it is today on airstrikes in Iraq (54 percent).
But that's a pretty broad range. And in any case, it would be a dicey political decision -- and potentially a pretty unpopular one.
This is the political backdrop on which the White House is making its decision.