I’m trying to define exactly what it is about Obama I’m finding so dissatisfying. It’s not necessarily his politics. He’s more or less center, I’m center-left on most things. We’re not that far apart. It’s not his pragmatism. I’m a pragmatist, too. God knows we could use more of that in our politics now. No, I think what it is is how he seems to get his ass handed to him so often.

Compare and contrast with Bill Clinton, the Great Triangulator. Clinton often didn’t seem to stand for anything, but in retrospect, I was more consistently happy with his tenure while it was happening than I am with Obama’s. After the mid-terms of 1994 culminating with the federal government shut-downs of 1995 and 1996, you could always see what Clinton got as part of any deal. He didn’t get everything he wanted, but he got something. As hard as the right tried to minimize him and hand him defeat, he always seemed to come out the other side with at least a partial victory. At least, that’s how I remember it.

These days, Obama talks a good game, but he doesn’t seem comfortable in his presidential skin. There are flashes of presidential behavior (Bin Laden), but for the most part he seems like one of those overly obsequious parents who never stops negotiating with a willful child and, ultimately, never seems to make any headway in stemming their willfulness. For someone who ran such a masterful campaign to win the Presidency, he seems to have no idea what Americans think makes a successful president.

A classic example is the 14th amendment option (the one that says the debt of the United States will not be called into question). At a very early point in the debate, Obama said he would not exercise it. No, it had never been done before and, yes, had he done so, it would have likely ended up in court, but it was an option. It was a negotiation ploy. It was a freakin’ stick! Instead, he got all professorial and appealed to his opposition’s better angels. Guess what? They don’t have any. At least not when dealing with him. They know better by now. In any event, Clinton’s position on the 14th was that hell yes he’d use it “without hesitation, and force the courts to stop me.” See?! Sounds like a president to me.

Three times he put the extinguishing of tax breaks for the wealthy out there as his objective towards reaching a more equitable solution to our budget imbalances. Three times he kicked the can down the alley until next time. What happens when there are no more next times? Clinton understood far better (and sooner) than Obama that in order to lead you have to look like you’re winning every once in a while. Obama never seems to win. Health care reform, for example, was so watered down and limp as to have seemed hollow at best.

Even when he wins, it smells like a defeat.