Maybe Tom O’Brien’s brother, BC head football coach Bill O’Brien, could defeat Mayor Wu. He’s got decent name recognition. But Tom? Not so much. O’Brien, the former city development czar who plans to announce next week that he’s running for mayor, may be well known within business circles and parts of East Boston, where his investment company has been redeveloping the old Suffolk Downs site. But he’s a non-entity to the vast majority of voters in Boston. The best he can do, I figure, is squeeze past the other mayoral challenger in the race, Josh Kraft, for a head-to-head contest against Wu in November. And then she beats him. …  

A quick aside: Boston’s business community must really be in a lather these days. O’Brien is the second candidate, after Kraft, to emerge from the general business/establishment world to challenge Wu. Those in the business community talk amongst themselves. They gripe amongst themselves. They reinforce each other’s negative opinions that Wu is a disaster for the business community. They assume everyone else is unhappy with her too. And so … you get candidates like O’Brien and Kraft.