King Sal

In 1976, a 31-year-old DiMasi lost his first race for state representative. He was challenging an incumbent, and came up 140 votes short in a four-way contest. Two years later, the seat opened up, and he won it in a tight seven-way race. He wasted little time establishing a reputation for being willing to take swings at heavyweights. In 1981, Kevin White, the most powerful mayor Boston had ever seen, pressed the State House to pass a $75 million budget bailout, claiming he needed the money to hire cops. DiMasi intimated that White might just funnel the money back into his sprawling political machine, and called for restrictions on how the funds could be spent. White responded by calling DiMasi a quisling in the papers, and took out a billboard against the young rep that essentially said if residents called 9-1-1 and nobody showed up, it was this guy’s fault. Boston cops began ticketing and towing the cars of DiMasi’s campaign contributors. And through it all, DiMasi basked in the limelight the conflict brought. He gave a television interview and said, “The mayor is harassing people in my neighborhood to extort my vote. I said, ‘People in my community voted for me to be in office so that I would do the right thing, and that’s what I’m gonna do.'” In the end, the bailout went through, with the restrictions.

Four years later, DiMasi would be presented with the opportunity to take a whack at another giant when he and his buddy Tom Finneran (the two sat next to each other as freshmen reps) put themselves on the track to leadership by helping overthrow Tom McGee, the autocratic House boss from Lynn. “He was a strong, do-as-I-say speaker, and he wouldn’t leave,” DiMasi recalls. “Even though his time had come.” The last House revolt, 20 years earlier, had failed, and the retribution that followed shattered careers. This time, however, the rebellion, led by Everett’s George Keverian, succeeded. DiMasi and Finneran both netted chairmanships; just over a year later, DiMasi was heading the influential Judiciary Committee. However bold the move appears in retrospect, the pair likely wouldn’t have risked angering McGee if the speaker had had the votes to hold on to his post. But they read the political winds correctly, broke in front of them, and profited handsomely.

Photograph by John Goodman

During his 30 years in the legislature, DiMasi has come to deeply respect the House’s role in shaping state affairs, as he’ll tell you, repeatedly. He has also seen how well-intentioned but myopic policy can have disastrous consequences for the chamber’s standing (not to mention its members’ reelection campaigns), such as when, back in 1988, Governor Michael Dukakis pushed through a bill mandating universal healthcare. The business community had opposed the legislation fiercely, and after the bill was passed against their wishes, they rallied and managed to get it repealed before it was ever implemented. The lesson was that big legislation has to be consensus legislation, or else it won’t survive.

Things would get worse in the years that followed, as the state suffered through a fiscal crisis brought on by chronic overspending. With the economy crippled, social programs had to be cut, and Speaker Keverian found himself in the unenviable position of having to enlist support for a multibillion-dollar tax increase. Twenty-five representatives and state senators lost their seats in the aftermath, and another 32 chose not to seek reelection. DiMasi, though, was spared: He was home recuperating from a minor cardiac episode. Keverian had called him up and asked if he was well enough to come to Beacon Hill and help vote through the hike. DiMasi’s response prefigured his dealings with Deval Patrick: “Mr. Speaker,” he said, “with all due respect, I’m home recovering from a heart attack, not a lobotomy.”

It is lines like that that make it hard for a lot of people to get past DiMasi the wiseass. In public life, especially in Boston, humor gets you easy press, but it also can prompt others to dismiss you as little more than a funny guy—and DiMasi certainly is a funny guy. During an Ireland-Italy soccer match in 1992, he got former Mayor Ray Flynn to close down Hanover Street. Before the game, DiMasi addressed the crowd, floating a wager with Flynn: free dinner for the winner in the loser’s neighborhood. Then he had second thoughts. “I said, ‘What am I talking about? Dinner in South Boston? I lose either way!'” In 2004, when Representative Reed Hillman’s farewell speech to the House consisted of saying, “Thanks,” DiMasi dubbed it “his best speech yet.” Former Governor Paul Cellucci recalls when, during his own tenure in the House, he would be haranguing the Democratic leadership, and “Sal used to come up and whisper in our ears, ‘Why are you wasting our time? You’re Republicans. In Massachusetts. You’ll never amount to anything!'” After hugging Mitt Romney in 2004, DiMasi told the press that the only thing he got out of it was “frostbite.”

The breezy punch lines, however, obscure a formidable intellect. “I used to tell him, ‘Sal, people don’t realize how smart you are,'” says Arline Isaacson, cochair of the Massachusetts Gay and Lesbian Political Caucus and a longtime fixture in the halls of the State House. “People just don’t see it coming.” That’s probably no accident. Jack Connors says DiMasi has “one of the greatest minds I’ve ever seen,” but notes that “he doesn’t lead with the smart. And I think that disarms a lot of people.”

Certainly, he’s been smart enough to know how to get what he wants. DiMasi was in his fourth year as House majority leader when Speaker Tom Finneran became embattled by allegations of perjury and found himself the principal target of Mitt Romney’s bitter 2004 bid to elect Republicans to the legislature. Finneran parachuted into a high-paying job atop the Massachusetts Biotechnology Council, and then into a federal plea on felony obstruction of justice. (His predecessor, Charlie Flaherty, succumbed to federal tax-evasion charges. His predecessor, Keverian, is known to joke that he’s the only speaker in the past two decades not to become a federal felon, adding that, since DiMasi is from the North End, his streak should be safe.) During the ensuing skirmish for the speakership, DiMasi was confronted by a strong challenge from Ways and Means chair John Rogers. He overcame it with a tactic that took finesse for him, as a former Finneran henchman, to pull off: reaching out to the same liberals Finneran had run roughshod over during his tenure.

After DiMasi won the speaker’s post, the media predicted that if the jokester’s House didn’t just drift around, rudderless, it would swing wildly to the left—something that initially worried the business community, which had preferred Rogers. DiMasi still bristles at those early predictions. If anything, he’s been a hands-on speaker who takes great pleasure in playing around in policy minutiae. Ideologically speaking, he’s taken complex (or nuanced, or slippery, depending on your mood) positions, and it’s been difficult to gauge where his leadership team will fall on a given issue—a dramatic departure from the way the House ran under Finneran. Members also haven’t complained about the lawmaking process as vociferously, or as often, or as publicly as they did under “King Tom,” largely because DiMasi has taken pains to keep reps from both ends of the political spectrum happy. While centrists hold the House’s key leadership posts, DiMasi has continued to empower—co-opt, critics might say—the leftist opposition that nipped at his predecessor’s ankles. Social progressives chair several committees, and their bills now at least come up for a vote, which is far more than they used to get. Meanwhile, the House’s conservative ranks are mollified by the speaker’s hawkish fiscal policies. DiMasi has managed, for the moment, to be all things to all people—or at least most things to the people you most need to keep happy. And because of that, he can get away with wrapping himself in teary-eyed concern for the poor at the same time he’s fighting tooth and nail to hold the line on spending. “The House traditionally has been the steady hand of the budget,” he says, invoking the lessons learned in his decades on the House floor. Of the fiscal crisis of the late ’80s, he adds, puffing out his chest slightly, “We’d never want that to happen again. I’ve always been fiscally responsible. If people understood what was going on at the State House, they’d understand [that].”

If Finneran ruled by fiat, DiMasi crafts legislation largely by the Socratic method. When he meets with his leadership team, he seldom hands down edicts, or even takes a stance on the issue up for debate. He prefers asking questions, poking holes in positions, and forcing his deputies to defend the choices they’ve made. “They learn quickly that they’ve gotta be prepared to answer questions when they come in,” he says. Representative Paul Donato, one of the speaker’s closest House confidants, says members know that if they disagree with a bill, they’re welcome to visit DiMasi’s office to air their concerns. But while DiMasi has made good on his promise that his post-Finneran House would engender more openness, that openness, it appears, is a relative thing. In DiMasi’s system, all the talking that happens as members mull legislation and House leaders strive for consensus tends to happen behind closed office doors, far away from reporters’—and occasionally his own legislative colleagues’—prying ears. Representative Frank Smizik, one of the liberals who suffered under Finneran and who is prospering under DiMasi, praises the speaker for being “more willing to let something come to the floor” than Finneran (who, to cite just one example, routinely stonewalled every environmental bill in committee). But he bemoans the fact that most heavy lifting happens “behind the scenes,” outside the House chamber proper. When a piece of legislation finally emerges from those backroom sessions, that means it’s been fully subjected to DiMasi’s rigorous vetting, and therefore should be considered a finished product, not to be tampered with.

For DiMasi, keeping deliberations private helps minimize public conflict, and allows him and his House to speak with a more-or-less-united voice. That’s a striking stylistic contrast to Patrick, who doesn’t float trial balloons so much as trial zeppelins, issuing flurries of press releases addressing some problem or other, and then hoping the proposals, backed by his sweeping oratory, will win over the legislature—about as far from Sal’s way as he could possibly be.

During the run-up to last summer’s vote on a constitutional amendment banning gay marriage, DiMasi and Arline Isaacson would sit together, scrutinizing lists of House members’ names and how they were likely to vote. The speaker would summon legislators to his office, and they’d talk. “Most people assumed he’d threatened them,” Isaacson says. “Truthfully, I wanted him to. He wouldn’t. He went through painfully long conversations, one after the other, to get them to vote the right way.” Some legislators did try to cut deals. By every indication, DiMasi refused to bargain with them, and most wound up voting against him. “The gay-marriage vote was huge,” says Representative Brian Wallace, one of the late converts who helped sink the amendment. “And Sal never pressured me. He’s never twisted my arm on one vote.” The same was true of the state’s landmark 2006 healthcare reform bill, which hovered near death on many occasions as DiMasi wrangled diametrically opposed interest groups and gradually talked them into agreeing with each other. Rick Lord, president of Associated Industries of Massachusetts, worked closely with DiMasi on the bill. “The speaker would only pass this when we had broad consensus, and he pushed really hard” to get all the parties there, says Lord. Now, thinking of how Romney has traveled the country touting his healthcare bill, DiMasi chortles. One Time article called healthcare “Mitt Romney’s defining moment.” The article “gave Romney an awful lot of credit,” he says. “It’s easy to make Power-Point presentations without specifics.”