Running into trouble?

Or the quirky 11th-hour alliance between the second- and third-place primary finishers, who believed that united they could topple the longest-serving mayor in city history.

Quirky might be good, but it didn’t turn out to be better, at least not in the minds of Boston voters. They sent Michael F. Flaherty to a hard-fought but sound defeat in the 2009 mayor’s race. True, Flaherty came closer than any Menino challenger ever had, but that isn’t really saying much. Menino garnered 57 percent of the vote, cruising to a 15-point win.

It was Flaherty’s classic, coulda-been-a-contender moment. And since then, his challenge has been to craft an encore. For months now, he has been semipublicly mulling a run for the City Council and is said to be close to announcing a decision, maybe as soon as next week.

For many of us, returning to a job we held for 10 years wouldn’t hold much appeal. But Flaherty, who didn’t return a call for this column, has told fellow politicians that he misses the job, especially the exposure, which is hard to generate from a downtown law practice. Goodness knows he isn’t the first former pol to miss being close to the action. Also, he has never made any secret of his desire to run for mayor again, but it turns out that four years is a long time to try to stay viable. He believes he can finish first on the ticket this year, setting himself up as the heir apparent to Menino.

Flaherty lost his bid for mayor for a lot of reasons, but one was overriding: Voters didn’t really buy him, the scion of an old-school South Boston political family, as the face of the “new Boston.’’ Despite a solid record of service, he lost heavily outside South Boston. And that is where this supposed return to glory begins to run aground.

The current councilors at large, in case you have trouble remembering, are Stephen Murphy, John Connolly, Felix Arroyo, and Ayanna Pressley. All of them are running for reelection, which means that Flaherty would have knock off one of them to reclaim his old seat. Arroyo and Pressley happen to have finished third and fourth two years ago.

Pressley is the first woman of color on the council. Arroyo is its lone Latino. Though both have turned in impressive first terms, the politics of an off-year race, in which liberals and voters of color usually turn out in far smaller numbers, would probably favor Flaherty. But does knocking one of them out of office really help his chances of becoming the next mayor?

Sure, Flaherty would have a great chance of winning, and perhaps of finishing first, which is no small matter. Even with South Boston for a base, he wouldn’t be a lock to sail past Connolly and Murphy, and alienating a big chunk of voters could make his a Pyrrhic victory.

There’s no clear blueprint for becoming mayor. Kevin White never spent a day on the City Council, though he served as Massachusetts secretary of state. Raymond Flynn topped the City Council ticket in 1981, then won the mayor’s race in 1983. Menino, then a district councilor, was a little-known quantity to many voters until he became acting mayor in July 1993, then won election easily.

Still, Flaherty’s big problem in the last campaign — how to position himself as a voice for the city’s future — hasn’t gone away.

And it will be a major issue in a race that would pit him, essentially, against two people of color. Flaherty wants to be the future, but the present keeps standing in his way.

Adrian Walker is a Globe columnist. He can be reached at walker@globe.com.