Bobby Valentine Managed the Mets. Running for Mayor Should Be a Cakewalk

“Do we have time to swing by my old house?” he asks his campaign manager, Dan Miller, who’s behind the wheel. Not really, says Miller, 41, a slender finance executive who was Bobby V’s neighbor for a time and has taken on his mayoral campaign as an unpaid side hustle. We’re due down at the waterfront in 15 minutes, near Bobby’s favorite diving rock from back in the day, to join the 9:30 a.m. sharing circle at a summer program for local kids, mostly Hispanic, mostly first-generation, who catch up on school in the morning and learn to sail in the afternoon. Valentine’s old house isn’t on the way, but it’s not not on the way. Miller steers the BMW off course, and Bobby V starts tour-guiding.

We pass St. Clement’s Church, where he took confirmation and where the boys got into fistfights in the parking lot. We pass the elementary school where the boys got into fistfights in the parking lot. We pass his ex-girlfriend’s house. We pass his big brother Joe’s machine shop. We pass his big brother Joe. (“Hey, ya jerk, stop blocking the road!”) We pass Rippowam High, where he was a teenage phenom. We skip Stamford High, Rippowam’s mortal enemy. Finally, we roll to a stop in front of an ugly abandoned concrete lump with a faded sign that reads “PLASMA AIR INTERNATIONAL.”

Bobby V laughs. “And that’s where my house used to be.”

Everywhere he goes, Valentine knows everybody, plus at least one member of their extended family. In the parking lot of Beldotti Bakery (“best Italian bakery in Stamford”) he kibitzes with some rabbis from the neighborhood about how he was here just yesterday, kibitzing in the parking lot with some priests from the neighborhood. “What an ecumenical bakery!” he declares. At Twin Rinks across town, where kids from the local Boys and Girls Club camp are trying out ice skating for the first time, Valentine gets a bear-hug from the camp’s director, Ashton Dominique, who’s known Bobby V for 16 years. “You can count on him,” Dominique says over the din of stumbling kids. He only told Bobby about this event a few days ago, “and boom—he’s here.” Before the kids hit the ice, he asks Bobby V to offer a few words of encouragement, then stands aside as Valentine spins an elegant, on-the-fly metaphor about how learning to skate is a lot like life: You get out there, you wobble, you fall, you get back up, you try again, and before you know it you’re flying.

If you ask Bobby V, there is no finer place in America than Stamford, Connecticut, but he also doesn’t harbor any illusions about its relative majesty. It’s not Waikiki. It’s not even Westport. It’s a Metro North stop on the New Haven line, 59 minutes via express train from Grand Central. It’s a stretch of freeway exits on the way to Boston. It’s a finance outpost of 130,000 with the charmless office towers to match. “I mean, it’s not the dirt, you know? It’s the people,” he says. “The community, my entire life, took care of me.” So yes, of course Bobby V wants to be the mayor of Stamford. Of course he thinks he’s the obvious choice. He may not have the job yet, but in all kinds of ways, he’s already been the mayor of Stamford for years.

“I’m gonna get killed for saying this, but I’m gonna say it anyway.”

Yes. That’s more like it. Bobby V—back in the saddle! If someone attempted to capture the essence of Bobby Valentine in a single Bobby Valentine quote, it’d be hard to do better than I’m gonna get killed for saying this, but I’m gonna say it anyway. It’s lunchtime in downtown Stamford and all the patios are packed. In 1980, after his playing career ended, Bobby V opened Bobby Valentine’s Sports Gallery Cafe around the corner from here at 225 Main Street. He ran it for 37 years, through his entire managerial career, then relocated to a 20,000-foot wood-panelled fortress two blocks away at 268 Atlantic Street, which he rechristened Bobby V’s Restaurant and Sports Bar. Great potato skins. This Italian spot is right in between. His campaign staffers—young, diverse, new at this—sit in silence, loins girded.

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