Future Mayor Tommy Wells? Photo by Amber Wilkie

We’re approaching the halfway point of 2012 and Mayor Vince Gray is looking more and more vulnerable by the day. That can only mean one thing—it’s time to speculate as to who could challenge or replace him come 2014.

Over the weekend the Post kicked off the speculation and rumor-mongering with an article that identified three current members of the D.C. Council that might be looking at taking Gray’s seat: Jack Evans (D-Ward 2), Muriel Bowser (D-Ward 4) and Tommy Wells (D-Ward 6). The three have been meeting with key political players, burnishing their resumes and started to draft their pitches to a citywide audience.

Of course, it’s not just the three of them that are looking to move up in the city’s small political world:

Other D.C. Council members have an eye on higher office, but they have not moved as conspicuously as Bowser, Evans and Wells. They include at-large members Michael A. Brown (I), David A. Catania (I), Phil Mendelson (D) and Vincent B. Orange (D).

In light of the appeal of an outsider in a political crisis, speculation has also emerged about potential wild-card candidates such as Police Chief Cathy L. Lanier, U.S. Attorney Ronald C. Machen Jr. and Machen’s top assistant, Vincent H. Cohen Jr.

This is all fine and good, but it seems to ignore the awkward political realities that any mayoral hopeful may have to face over the next few months—especially if Gray resigns or is forced to step down. If that happens, D.C. Council Chair Kwame Brown would become mayor until a special election could be scheduled. Brown, though, is himself the subject of a federal investigation, though, so there’s a chance he could go too.

If that were the case, the four at-large councilmembers—Mendelson, Brown, Orange and Catania—would have to decide among themselves who would be elevated to the level of mayor until a special election and who would become chair. (As the City Paper has noted, Mendelson could well be elevated.)

After that, true mayoral contenders would have to decide whether they’d want to risk it with a special election to fill what’s left of Gray’s term or just wait until the April 2014 primary and go all in.

The usual caveats of course apply. Evans has always had citywide ambitions, but there’s still little evidence that he has the needed citywide appeal. Wells is a progressive standard-bearer, but 2014 may be one election cycle too early for a white mayor. Bowser—whose name has been floated before—comes from vote-rich Ward 4 and can present herself as a second-coming of Adrian Fenty, though it’s unclear that that appeal is enough to outweigh perceived connections to troublesome old school D.C. power-brokers. As for Machen and Lanier, well, it’s probably way more fun being popular bosses of their respective domains than elected officeholders. (On NewsTalk with Bruce DePuyt today, Lanier waived away any political speculation: “I just signed a five-year contract,” she said. “I have a job.”)

There’s also the distant possibility that Gray will emerge unscathed from the current scandal and run again. Crazier things have happened in D.C., after all. (See Barry, Marion.)