Webb in 2012. (Photo by Katherine Frey/The Washington Post)

The on-paper version of former Virginia senator Jim Webb checks a lot of the boxes on the "Does this person look presidential?" checklist (available by the metric ton at any major news outlet). A decorated Vietnam veteran and secretary of the Navy under Ronald Reagan, Webb, as a Democrat, unseated an incumbent Republican senator in the swing state of Virginia. And he has a good head of hair and a charming touch of drawl in his voice as he announces his candidacy and pitches a return to the political center.

"Is it possible," he asks, "that our next President could actually lay out a vision for the country, and create an environment where leaders from both parties and from all philosophies would feel compelled to work together for the good of the country, despite all of the money and political pressure that now demands they disagree?" His answer, you will be surprised to learn, is: Yes.

Webb's got some bona fides on a "centrist" pitch. When he was in the Senate, according to analysis from GovTrack.us, he was among the Democrats furthest to the right ideologically in his Congress. The Democratic Party's newly embraced panic over the votes of working-class whites is a drum Webb began beating in 2010, as Bloomberg's Dave Weigel noted on Thursday.


But Webb is also much more inexperienced in electoral politics than you might think. All of the references above to his being a former senator skip over the fact that he served one term, from 2006 to 2012, choosing not to run again. And when he won in 2006, it was by the skin of his teeth; or, perhaps more accurately, by someone else's skin entirely. Sen. George Allen's weird reference to a Democratic tracker, who was an Indian American, was one of the first scandals to go Internet-video-viral. And yet Webb still only barely beat Allen (R-Va.), by just over 9,000 votes out of 2.3 million cast -- in 2006, a strong Democratic wave election. Democrats won the House by an eight-percentage-point margin. Webb couldn't manage a one-point margin against the "macaca" guy.

What's more, Webb actually underperformed with the constituencies that he was tut-tutting about in 2010, relative to the national totals. He won voters with incomes under $50,000 by eight points, according to exit polls; Democratic House candidates nationally won them by 12. Webb actually lost among voters who made less than $100,000 and won those making more, the inverse of the rest of his party. If Webb wants to argue that he knows how to lure working-class voters, he can't point to numbers to make that case.

Webb was a great candidate for Democrats in Virginia in 2006. The state was just transitioning from more-Republican to more-Democratic than the nation as a whole in presidential elections, meaning that it wasn't a sure thing for either party to win. Webb could critique George W. Bush on the unpopular Iraq War from the space of being a veteran and a former Reagan military official. (Regardless, he did worse than national Democrats among voters who thought Iraq was an important issue.) That was helpful in 2006. In 2016, it's not clear that his national security credentials will seem similarly useful, especially if he's going up against a former secretary of state named Hillary Clinton.

If nothing else, Webb's candidacy is evocative of another former presidential contender: Wesley Clark. Clark became a bit of a darling when a possible candidacy first emerged. A former Army general, he seemed well-poised to lead the party's efforts to position itself as able to fix the problems with the wars in Iraq and Afghanistan. He checked off a lot of boxes on that checklist, too, but his campaign never really got off the ground.

There are other reasons for skepticism -- that we assumed in September might prevent Webb from making this announcement at all. (The word "Confederacy" makes an appearance, which is not one of the things most Democrats look for in a candidate.)

We have come to the point at which we say, "you never know," which is the last box on the "How to write about 2016" checklist (also available in bulk). And you don't ever know. But maybe if we could look at more than one election that Webb barely won, we'd be able to know a bit better.