The Muckraker: Mr. Freeze

Tom Menino has long been known as a man you do not want to cross. Just ask Ray Flynn, who reportedly ran afoul of Menino back in 1993 while preparing to hand over the mayoralty to his longtime friend. It started right after the announcement that President Bill Clinton had tapped Flynn to become ambassador to the Vatican, a move that would elevate Menino, then city council president, to acting mayor.

An eager Menino had an aide clear out a room near Flynn's office to be used as his own temporary workspace. Flynn immediately ordered it returned to its former use. When Menino complained, Flynn shrugged him off—and, just like that, went from Menino ally to a member of what's known in local power circles as the mayor's enemies list.

To this day, Flynn claims, his notes to Menino go unacknowledged, his occasional advice pointedly ignored. “I really can't tell you what happened,” Flynn says. “I stopped trying to figure it out.”

Raybo, you're not alone. No one much bothers to analyze what makes Boston's mayor for life turn against someone, any more than we wonder why January is cold. In certain circles, it's simply a given that Menino bruises easily, broods eternally over real and perceived slights, and gets both mad and even. “Once you're out, you can never, never get back in,” says Maura Hennigan, who during her failed mayoral bid tried to use Menino's allegedly vindictive temperament as evidence he'd grown too insular and petty to govern effectively. In the local media, “thin-skinned” has been applied to Menino so often it's become a permanent tattoo.

Predictably, Menino says the conventional wisdom has him all wrong: “I'm not thin-skinned. I can't be—I'm open to people. I've worked with a lot of folks who I've had disagreements with. I don't shut my door to people.” Self-serving? To a point. But while it may surprise those who accept the stereotype of Menino as Captain Queeg in a Filene's Basement suit, it turns out there's more truth than spin in his denial. Interviews with Menino's friends as well as prominent figures on his supposed enemies list suggest that as the mayor begins his fourth term this month, it's time for a new appreciation of his hair-trigger temper: Rather than a sign of reflexive arrogance, it could well be the cultivated tool of a veteran politician who uses fear to instill obedience and respect.

After all, as one veteran politico puts it, “if you never screw with people, you'll never be a decent pol.”

At its most damning, the popular critique of Menino argues that his ego, when wounded, can ride roughshod over the interests of the city. As evidence, critics point to such things as the ugly row between the mayor and Firefighters Local 718. In January 2001, firefighters picketing the annual State of the City address reportedly spat at the mayor's wife, Angela, as she entered John Hancock Hall. (To make matters worse, says a source close to Menino, the mayor heard a heckling firefighter refer to Mrs. Menino with a vulgar term for a part of the female anatomy.) Later that year, union picketers got into an obscenity-laced exchange with Susan Menino Fenton, the mayor's daughter, within earshot of his three-year-old granddaughter, Giulia. The mayor was livid. “Mess with the daughter or the wife or the grandkids,” says an ally, “and it's lights out.” But Menino's rage, while understandable, did nothing to advance the public interest. When his stalemate with Local 718 finally ended, the firefighters got a contract that Menino's detractors contend failed to include significant benefits for the city.

Dysfunction is also said to mark Menino's relationships with local developers, most notably Frank McCourt. It's unclear why things went sour between Menino and McCourt, but there's no mistaking signs of a feud. Since buying the Los Angeles Dodgers in 2004, McCourt, who owns 24 prime acres on the Seaport frontier, has unflatteringly compared Boston City Hall with officials in L.A., a place where, he says, “things are happening, as opposed to where things are talked about happening.” The Menino camp, for its part, reportedly refers to McCourt as a “parking attendant.” Observers say each side has brusquely dismissed the other's attempts to reach détente. Meanwhile, McCourt's parcel sits undeveloped, leaving a big hole in Menino's long-stagnant plan for the waterfront.

Plenty of other local players claim to have learned that messing with Tommy Menino can be bad for business. Hennigan says one of her supporters, a local fashion designer, was punished by having her application for small-business assistance rejected by a City Hall staffer, who, Hennigan says, “even told her how much money she had given me.” Prominent public relations executive Larry Rasky notoriously paid the price for squaring off against Menino during the 1980s. At the time, City Councilor Menino was refusing to play ball on a measure concerning Cablevision, where Rasky was director of government relations. Rasky told a reporter that he could have won Menino's support if he'd been willing to give him free cable service. “He said Tommy could be bought for nine bucks a month, ” recalls a Menino friend. “That was completely unacceptable.” A source close to the situation says the mayor has since badmouthed Rasky to current or potential clients, at times using a 12-letter pejorative explicitly banned by the FCC.

Striking fear in subordinates is a standard management tactic. But for a mayor occasionally portrayed as having a less than formidable intellect (and who certainly lacks a motivational speaker's persuasive diction), being seen as touchy and prone to hold grudges may be an especially effective tool.

Sometimes the very thought of angering the boss can help keep the troops in line, as Menino demonstrated last year when city council candidate Sam Yoon showed up at a news conference to receive an endorsement from the Black Political Task Force. Yoon discovered to his dismay that the event was also a Hennigan rally, sending his campaign scrambling to explain that he was neutral in the mayoral race and hadn't known what he was walking into. Yoon's discomfort was minor, however, compared with that of City Councilor Paul Scapicchio, who had just endorsed Yoon. Scapicchio denies reports that Menino chewed him out about the Yoon-Hennigan photo op. But he as much as admits to being hypersensitive to risking the mayor's wrath.

“I told (Yoon), 'I'm supporting Menino, tell me you're running your own race,'” says Scapicchio. “To then see him onstage with Hennigan's arms around him, it just sat really badly with me.” The mere threat of a mayoral hissy fit was enough to send a potent caution signal to a council ally and provide a graphic peek at how things work in City Hall for a newcomer of uncertain allegiance.

If Menino's short fuse were paired with a Nixonian relish for everlasting spite, the mayor might risk breeding the deep resentment that can undermine a political agenda. But those who've clashed with Menino have often found him willing to quietly forgive, or at least forget. “We've had occasional moments, but we make up the way all Italian men do: We go out, we eat,” says Boston Herald deputy managing editor Joe Sciacca. “He's open about what he doesn't like, but I've never found him to be personally vindictive.” Indeed, despite all the elbows Menino has exchanged with the press, he remains the state's most accessible major public figure. Herald columnist Howie Carr, an unrelenting chronicler of Menino's malapropisms, says, “I don't think I'm his enemy. I just enjoy making sport of the guy.” One of Menino's oldest friends agrees. “Howie calls him 'Mumbles.' That is not breaking Menino's balls. He knows he can't talk straight. He makes fun of it in his own ads.”

Those who blame Menino's alleged tiff with McCourt for gridlocked Seaport development should note how the mayor leaned on the Pritzker family last summer to sell their dormant property on Fan Pier to Boston developer Joseph Fallon. “I put a hard fastball under his chin,” Menino himself says of the move, which could lead to McCourt's finally reaping a windfall from his parcel—not a poor outcome for someone on Menino's bad side. And despite his well-documented animus toward Rasky, Menino has stopped far short of trying to destroy him. “This is something both the mayor and I have long put behind us,” says Rasky, whose PR business, tellingly, has flourished during Menino's reign. Rasky represents the Red Sox, who rely heavily on Menino's good graces to operate their various enterprises, observes one mayoral ally. “Do you really think he'd still be there if Menino wanted him gone?”

While running for an at-large council seat last summer, Ray Flynn's son, Ed, had reason to be apprehensive toward the mayor. But Menino treated him with a graciousness that heartened the elder Flynn. “I was very pleased with the friendly and respectful demeanor he extended to [Ed] whenever he saw him during the campaign,” Ray Flynn says, adding, “If there's something there that Tom Menino doesn't necessarily agree with me on in the past, it certainly doesn't extend to my son.”

It remains to be seen whether this marks the beginning of a thaw in Menino's frigid relationship with Flynn. Either way, Flynn is willing to concede the merits of his successor's approach.

“I woke up every day thinking of how I could be kind to people,” Flynn says of his own time as mayor. “But you don't get the best out of people by consistently telling them how wonderful they are. Menino's style may be right. If I had to judge which of the two styles works better, I'd have to say his does.”