Why did Tom O’Brien decide not to run for mayor against Wu, Kraft?

If you’re going to take a shot at the queen, you’d better not miss.So what does that mean for Tom O’Brien? That’s a head-scratching predicament for one of Boston’s biggest real estate developers, and mayoral-hopeful-for-a-minute.Related: In reversal, developer Thomas O’Brien says he won’t challenge Mayor Wu after allYou may remember how just a week ago this town was abuzz over another challenger wanting to unseat Boston Mayor Michelle Wu in this fall’s election. O’Brien, who long ago served as planning chief under Mayor Tom Menino, would have joined New England Patriots family scion Josh Kraft as a third major candidate for two spots in the November runoff. O’Brien’s primary beef with Wu: She has been hostile to development.O’Brien had planned his campaign launch this week in East Boston, and his imminent entry was front page news on Saturday’s Globe. But by Monday, O’Brien had changed his mind, leaving the rest of us wondering what just happened.Get Starting PointA guide through the most important stories of the morning, delivered Monday through Friday.Enter EmailSign UpMore importantly for O’Brien’s future as a developer in this town, will the mayor forgive and forget? Or will she view his almost-candidacy the same as taking a shot at her? Boston mayors, Wu included, famously love to hold grudges against those who cross them.AdvertisementTongues are also wagging because O’Brien dropping out has to be a sigh of relief for both Kraft and Wu, albeit for different reasons. To Kraft, O’Brien would been fighting for the same disaffected and anyone-but-Wu voters and courting similar donors in the business community.My sense is that O’Brien was contemplating jumping in so late because he has been unimpressed with Kraft, who is running for office for the first time. Of course, O’Brien is also a political neophyte, but some view him as a more charismatic option with deep roots in community and who might have a better shot at beating Wu.AdvertisementFor Wu, O’Brien would have been another well-funded candidate to fend off, one who’s not tied to a famous billionaire who stirs mixed emotions in Boston. She also couldn’t have liked the prospect of two opponents hammering away at her perceived weaknesses: higher residential property taxes, budget challenges, the inability to build more housing, and her struggle to fix Boston Public Schools.So if both Kraft and Wu had something to gain by O’Brien staying out of the race, did either camp strike a deal to keep him on the sidelines?Mayoral candidate Josh Kraft greets Mayor Michelle Wu before he speaks at the annual St. Patrick’s Day Breakfast in Boston on March 16.

Mayoral candidate Josh Kraft greets Mayor Michelle Wu

a decommissioned power plant in Everett. They’ll need help developing it. O’Brien’s HYM Investment Group specializes in complex projects like redeveloping Suffolk Downs and partnering with New Balance on its Boston Landing campus in Allston-Brighton.I know you’re thinking what I’m thinking: So did Robert Kraft give O’Brien a wink and a nod: “Drop out, and I’ll take care of you?”Let’s just say both O’Brien and Kraft camps couldn’t respond fast enough when I asked that question. O’Brien, in a statement, said “no conversations directly or indirectly” have taken place and “nothing like that was a factor in my decision at all.” A Kraft family spokesperson in a statement noted: “Robert Kraft has had no contact with Tom O’Brien in over a decade and has had nothing to do with Tom’s decision to drop out of the Boston mayoral race.”AdvertisementNow the notion that Wu would cut a deal with any developer may seem preposterous, given her track record. But it is worth noting that O’Brien has supported one of her more controversial plans — her bid to increase commercial property taxes. That had some speculating that O’Brien might have jumped in the race to help her, by knocking out Kraft.So why the about-face by O’Brien? After all, he’d begun telling friends he was running before abruptly changing his mind.I have to think after he became front page news, reality caught up fast, and someone delivered him the unvarnished truth: His path to victory would be narrow against an incumbent and a billionaire’s son. One has a track record of whipping up votes in every corner of the city, while the other has access to unlimited funding.And if, as seems likely, O’Brien didn’t win the whole thing, he would be in the unenviable position of angering the current mayor or a future mayor. And in his line of work — where developers need the blessing of the mayor and their appointees for their projects to move forward — being on the wrong side of the mayor can ice you out of City Hall. Just ask Don Chiofaro.My best guess is O’Brien’s investors talked him out of running. O’Brien is inextricably linked to HYM, and a failed mayoral bid could have left the firm branded as a pariah in the city. If the risk was his alone to take, it’s quite likely O’Brien would still be in the race. But I have to think the potential financial fallout to investors, partners, and employees outweighed his own political ambitions.AdvertisementO’Brien still wasn’t ready to jump on the phone with me this week, but in a statement he said his decision “boiled down to the simple fact that the time was not right.”More than anything, O’Brien couldn’t afford to take a shot at the queen and miss. Better to walk away now than lose it all later.Shirley Leung is a Business columnist.