City Councilor Tito Jackson is making all the moves of a person who is preparing to launch a campaign. Whatever one makes of his chances — which, on paper, look rather slim — his candidacy would be a jolt for the city.

The answer, by law, is yes. But the real question is whether Mayor Martin J. Walsh is going to face serious competition. The increasingly likely answer to that question is also yes.

Jackson, who has represented Roxbury on the council since he succeeded Chuck Turner in 2011, has had a very interesting 2016. He emerged as a high-profile voice in the battle against the ballot question that would have lifted the cap on charter schools. The “No on 2” campaign won a resounding victory despite being heavily outspent, and despite the fact that Governor Charlie Baker was on the other side of the issue.

The “No on 2” folks ran an outstanding campaign in general, and Jackson’s performance in particular was eye-catching.


At the same time, he has emerged as a thorn in the side of his sometimes-friend Walsh, whom he endorsed four years ago. On education and public safety issues, Jackson has become a regular critic of the mayor.

He has been coy about his election plans. Jackson has stepped up his fund-raising, and has done nothing to discourage any speculation that he’s running. But he’s also resisted answering direct questions about his plans. (He declined to return calls for this column.) Maybe he simply hasn’t made up his mind yet.

For many reasons, Jackson faces a serious uphill battle. For one thing, running for mayor costs a lot of money, and Jackson doesn’t have a lot of money. The $32,000 in campaign cash listed on his latest state filing would barely run a mayoral campaign for a month. He has hired a national fund-raising firm to help raise money, even as he declines to say what office he is running for.


Jackson’s cash problem isn’t going to go away. Traditionally, donors are deeply reluctant to give to opponents of a sitting mayor. There’s no good reason to make an enemy of the mayor unless you believe his opponent can really win. Given that a sitting Boston mayor hasn’t lost since 1949, that is a hard leap to get donors to make.

Walsh has not displayed the hardball spirit of his predecessor, Thomas Menino, in punishing opponents. Then again, he hasn’t faced an opponent as mayor yet. The people writing checks for Jackson will face a harder decision if he announces he’s running against Walsh.

“When you give money to an opponent, no matter who it is, that’s a statement that someone other than Marty should be running the city,” a politically active businessman said last week.

Walsh is not invulnerable. His name continues to surface in a federal investigation that has led to the indictment of two City Hall aides. The racial quagmire at Boston Latin continues to inflame his critics. But the economy is thriving, and Bostonians continue to perceive the mayor as a deeply decent person, and generally effective leader. There isn’t an obvious, glaring issue to use against him. It certainly won’t be charter schools; he and Jackson were on the same side of that fight.


None of this is to say that Jackson shouldn’t run. Menino coasted to his second term unopposed in 1997. He never had to defend his accomplishments, or explain where he hoped to guide the city. The term that followed was perhaps his least focused, and I’ve always believed his unopposed reelection had a lot to do with that. The city would have benefited from a race.

If Jackson does run, he will be counting on heavy support from those who currently feel alienated from City Hall. Walsh believes that his administration has been the most inclusive ever. A Walsh-Jackson race would likely put that belief to the test.

Adrian Walker is a Globe columnist. He can be reached at adrian.walker@globe.com. Follow him on Twitter @Adrian_Walker.