The Secrets of Their Successors

A nearly unthinkable twist of political fate could put three of the state's top elected offices up for grabs—a Hill-shaking scenario that already has would-be candidates plotting their ascent on the sly.

Illustration by Michael Witte

Illustration by Michael Witte

To get from Beacon Hill to Gatehouse Media’s community newspaper office in Needham, you have to strike out on the Mass. Pike, trundle south on I-95, then fight through the notorious Highland Avenue traffic, past the Petco and Staples stores. It’s a half-hour trip, which is fine if you’re in the market for some cat litter or a bulk supply of paper clips, but an indisputable hassle if you’re on your way to face a brigade of reporters assembled from Gatehouse’s collection of small weekly papers, which include the likes of the Needham Times, Newton Tab, and Wellesley Townsman. And if you’re coming from the State House, where ready-to-listen Globe and Herald scribes are always within spittle distance for Beacon Hill’s prodigious lip-flappers, schlepping so far to chat with the press seems a particular chore.

Nevertheless, there was state Treasurer Tim Cahill one sunny midsummer afternoon, sitting at the head of a dark table in an unadorned conference room. Dressed crisply in a white shirt with a yellow and black checked tie, he seemed positively enthusiastic as he fielded questions on the ins and outs of public school construction. (The topic has become a hobbyhorse for Cahill, who as part of his duties oversees all school building in the state.) Whenever he grew frustrated, he waved open palms in the air; when he wished to convey disappointment, he propped his elbows on the table and clasped his hands; and when he wanted to be emphatic, he executed a sort of air karate chop. Hands don’t talk like that unless you’re engaged, and Newton Tab editor Greg Reibman, for one, was impressed with Cahill’s performance. “I liked that when he didn’t know something, he told us he didn’t know it,” Reibman said. “Which is fairly refreshing.”

Between his constant gesticulating and his bright blond locks (always parted neatly on the right), Cahill comes off a bit like a grownup Dennis the Menace, if as Dennis reached maturity he hired a tailor and discovered the wonders of hair gel. Certainly, Cahill shares the cartoon character’s penchant for attention-grabbing mischief. Rather than quietly pushing from behind the scenes, the second-term treasurer has launched an unabashed crusade against ultradeluxe public schools, with the ostensible—and laudable—goal of saving taxpayer money. The other purpose of his efforts, of course, is to construct a reputation as a straight-talking, problem-solving knight in shining armor who’s looking out for your hard-earned money. More to the point, it’s to look like someone you’d want to vote for.

Cahill, a Quincy Democrat, worked his way up from city councilor and Norfolk County treasurer to his state treasurer’s post in 2003. Many say he’s long hoped for a higher office—and now it looks like he may have plenty of opportunity. If circumstances align, Massachusetts may be on the verge of an unprecedented political shakeup. This spring’s announcement of Senator Ted Kennedy’s brain cancer, combined with persistent rumors that Governor Deval Patrick and Senator John Kerry might take posts in a possible Obama administration (Patrick perhaps as attorney general and Kerry as a potential secretary of state), could mean as many as three vacancies atop the Massachusetts political ladder. It’s been over a century and a half since two Senate seats have had to be filled in the same year—the famed Daniel Webster and the not-so-famed John Davis both joined the chamber in 1845—but even then George Briggs was safely serving the second of his seven years as governor.

All this means that any politician with an eye on one of those spots had better be ready. The trick is not appearing to be too ready. It’d be bad enough to get caught plotting behind Kerry’s or Patrick’s back, but to come off as a vulture circling above Kennedy’s Senate seat would be the height of impropriety. Aside from angering Kennedy or turning off voters, that kind of overeagerness could alienate the assorted fundraisers, strategists, and kingmakers who inhabit the Massachusetts political apparatus. Lose them, and suddenly raising the cash and building the network necessary for a successful campaign becomes a lot more difficult.

Though the task before them is a thorny one, state officials able to kindle their political fires without giving off smoke stand to reap greater rewards than ever before. That’s largely because when the Democrats took control of the U.S. House of Representatives in 2006, our most powerful congressmen traded years of minority-party impotence for plum committee appointments, making them more influential in their current roles than they could be as newbie senators. Barney Frank, for instance, chairs the House Financial Services Committee (busy sorting out that little credit crisis) and Ed Markey heads up a new Select Committee on Energy Independence and Global Warming (also dealing with a few pressing matters). With those heavyweights likely—though, admittedly, not certainly—content to stay put, the door is open for relative newcomers like Cahill, Attorney General Martha Coakley, and Lieutenant Governor Tim Murray.

“None of these candidates have said to me, ‘This is what I’m thinking about doing,'” says Democratic fundraiser extraordinaire Steve Grossman. “But nevertheless, they are out there raising money, building a war chest, building relationships, appearing at events, staying in the mix.”

For Cahill, staying in the mix has meant mixing it up, but truth is, there are plenty of ways to skin this cat—and the strategies of his most active rivals in this not-yet-a-campaign hint not only at how they’ll present themselves to voters when the time comes, but also where battle lines will be drawn when the skirmishing breaks out into the open.


The Pit Bull

Cahill—a frequent breakfast and lunch partner of Grossman’s—has been by far the most aggressive in prepping for future office. First, he’s padded his campaign coffers with more than $3 million, $100,000 of which he raised between April and July. Law dictates that money collected by state officers can only be used in state campaigns (not federal ones), so that cash only helps Cahill if he opts to run for governor. But in a state where Republicans are more of a rumor than an actual presence, even more important than the dollars he’s raked in has been Cahill’s ability to use his position as treasurer to become a kind of one-man opposition party.

“Treasurers don’t generally move up to higher office, particularly governor or senator,” Grossman says. “They get pigeonholed as the keepers of financial resources, but not people who can represent the people of Massachusetts on the full range of issues.” Cahill is counteracting that assumption by essentially making like a glutton at a Bickford’s breakfast buffet: He’s taking bites out of anything that looks good. Since few people even know what it is, exactly, a treasurer does, Cahill has enjoyed the latitude to go after what he wants, making the job work for him.

Among many other things, that’s included dismissing the governor’s plan to bail the beleaguered Turnpike Authority out of debt as financially “reckless.” For his next course, he blocked Patrick’s proposal to draw $50 million from state pension funds to help out college students struggling to find loans—a shrewd move that allowed Cahill to paint himself as a responsible steward of retirement nest eggs while casting Patrick as a naive ideas man. More-cynical observers might note that it also gave him the chance to pander to seniors, who are known to show up on Election Day in far greater numbers than cash-strapped college kids. “He’s run a brilliant strategy,” says one veteran Democratic observer. “Whether or not it’s a winning one, it’s a hand he can play.”
The risk lies in this simple fact: Making your bones by making enemies is a dangerou
s game. A lot of people in state government, especially in the governor’s office, flat-out don’t like Cahill. “They hate him,” says that same well-connected observer. “He’s playing them, and I think they take that personally.”

Cahill has already felt the backlash of party bigwigs. In May, when state Democrats voted on whom to include in the 40-member delegation they’d be sending to their national convention, they passed over Cahill, choosing instead a little-known party member named Arthur Powell, who spends his days working as a credit manager at a Waltham biotech. The embarrassing defeat left Cahill as the only major Massachusetts political figure without a ticket to Denver.

So the question for Cahill becomes, Has he gambled too much in taking on the state’s Democratic establishment? Republican strategist Dan Winslow, for one, thinks Cahill has already burned too much of the left to survive a primary fight. The treasurer, he says, would be better off dropping out of his party and styling himself as a moderate Republican à la Bill Weld or Paul Celucci or even Mitt Romney (before his views “evolved”). While that’s not likely to happen, the suggestion ought to be worrisome for the confrontational Cahill, who makes himself a bigger target every time he fires off a new round. “When you set yourself up that way, you have to be very careful about your own record,” a Patrick administration insider told me in August. “It sometimes sets you up for charges of being hypocritical.” Incidentally, less than a week later, a story landed on the Globe‘s front page alleging the treasurer played favorites by kicking a scratch-ticket contract to a company that had brought on his friend (and, ahem, fundraiser) Thomas Kelly as a consultant. Given the article’s level of detail and random timing, someone had quite clearly tipped off the reporter—and it’d hardly be surprising if the dime dropped out of the governor’s office.


The Cause Célèbre

While Cahill has had to work hard to build a watchdog image, Attorney General Martha Coakley benefits from a job that naturally positions her in that role. In more than 20 years as a prosecutor, she has taken on a flurry of high-profile cases—she won prosecutions against the infamous British au pair Louise Woodward and several Catholic priests charged with sexual abuse—and become a familiar face for Massachusetts residents. In a recent Channel 7/Suffolk University poll, only 14 percent of respondents said they’d never heard of Coakley, while 48 percent said they had a positive view of her. By contrast, nearly twice as many people had never heard of Cahill and only roughly one in three said that they viewed him favorably.

If anything, the biggest knock on the AG might be that she’s not been more politically opportunistic. In that way, she’s the anti-Cahill: Her business-first attitude has earned her wide respect, but she lacks flash. Fortunately for her, Coakley’s got supporters eager to join in the dance she’s content to sit out.
Along with Bingham McCutchen partner and Coakley confidant Beth Boland, top-tier fundraiser Barbara Lee will cohost an October 21 fundraiser for the AG at the Liberty Hotel. Boland, who served as Coakley’s finance chair during her run for attorney general, says the event will feature the city’s “top businesswomen,” many of whom were key in Hillary Clinton’s primary win in Massachusetts. Maybe even more important than the money it’ll generate, the soiree will be a show of political strength for women still smarting from Clinton’s close nomination loss.

For a number of them, that disappointment has hardened their support for Coakley, who, no matter which contest she enters, is likely to be the only woman in the field. “What I really sense and feel is such a great sense of passion, frustration, resolve coming out of the presidential election,” says Boland, who cochaired the New England Lawyers for Hillary group. “We’re going to circle the wagons around our gal.”

Feminists like Lee—who says she’s ready “to go to bat” for Coakley—have long aspired to raise the profile of female politicians in a state that has yet to elect a woman governor or senator. And after suffering through Jane Swift’s helicopter-marred stand-in as governor and the tortured gubernatorial candidacies of Democrat Shannon O’Brien and Republican Kerry Healey, in Coakley, they just might have their standard-bearer. Coakley herself has much to gain from the relationship, since, as one analyst pointed out to me, she is much more a prosecutor than a politician—a polite way of saying she’s not great at raising money. While there aren’t exactly cobwebs growing inside Coakley’s war chest, her $600,000 is paltry in comparison with Cahill’s seven-figure stockpile.

The AG’s union with jilted Clinton backers is good for more than just get-togethers at fancy hotels. Being able to use Clinton’s organizational infrastructure could give Coakley an enormous advantage should she wind up seeking a Senate seat rather than the governor’s chair—which, as it happens, is the office she seems best poised to pursue. Here’s why: When a Senate seat opens midterm, a special election must be held between 145 and 160 days after it’s vacated, with a primary coming six weeks before that. With only three months to get a campaign up and running (and bankrolled), having access to Clinton’s well-oiled machine could be a big boost. If Coakley’s so inclined, the Liberty event could be the perfect chance to start galvanizing the troops.


The Opportunist

No doubt Tim Murray remembers what he saw in 2006, when the strength of his boss’s carefully cultivated grassroots networks pushed them both into office. That in mind, the lieutenant governor has been pressing the flesh everywhere this year—shooting bull at a clambake in Agawam, touring a school in Fall River, chewing the fat at a diner in Acushnet, and meeting with fishermen in Chatham, to name just a few stops.

“The guy is all over the place,” Boston City Councilor John Tobin says. “He’s doing his job as lieutenant governor, but Deval Patrick has let him be more of a partner than a guy who cuts ribbons.” Murray wasn’t just in Chatham to glad-hand, it turns out, but because Patrick has charged him with developing the state’s seaport economies. He’s taken lead roles on issues like affordable medication for seniors and has been the state’s point man in its contentious dispute over railroad track space with freight company CSX. And tellingly, all these places he visited are beyond the Boston power corridor. As the former mayor of Worcester, Murray understands the value of cultivating the outside-128 set.

At the same time, Murray has also become a practiced Beacon Hill operator. When Cahill ripped the administration’s debt-bailout plan for the Turnpike Authority, Murray was the one who fired back in the press, lobbing what was essentially his first salvo in what many see as an impending battle of the Tims. “When Cahill takes on the administration, what this really is is the Democratic primary fight,” says one operative. “In that respect, [Cahill’s] helping the lieutenant governor, too, because who would know the lieutenant governor if he wasn’t fighting with the treasurer?”

As for which primary he’ll be fighting in, Murray can keep his options open, much more so than Cahill and Coakley. Whereas the treasurer and the attorney general must always at least appear to be primarily focused on their job, nobody’s going to fault the presumed heir apparent to the governorship for gazing up a bit. Which is why the easy play for Murray—who could move up right away if the governor were to depart for Washington—would seem to be to bide his time and wait for Patrick to move on, whenever that might be. But the allure of the Senate is strong, and, as two sources close
to the Patrick administration pointed out to me recently, John Kerry was lieutenant governor when he embarked on his first senatorial campaign. Consider, too, that later this month Murray will lead a trade mission to Ireland, affixing to his résumé valuable international experience. What’s more, even if he were to run and fail in a Senate special election, he’d be able to return to his current role as if nothing happened.

The lieutenant governor is clearly preparing as if both roads are open to him. Over the summer, Murray raised a half-million dollars’ worth of eyebrows when it was reported that, through July, he’d pulled in $545,000 in state campaign dollars—$200,000 more than Patrick and almost $300,000 more than he had received during the same time period last year. He could use that money to fund his own corner-office campaign, or, as he’s been selling it to donors, funnel the cash into the Patrick-Murray reelection ticket in 2010. Of course, he has to position it that way. Even for him, it’d be imprudent to appear too eager.