Clean Sweep

In the world of Massachusetts politics, Doug Rubin has quietly become the man to see. Deval Patrick, Elizabeth Warren, Joe Kennedy III, and a parade of other new-generation progressives have all sought out the unassuming strategist to guide them into office. But can Rubin—known for his willingness to do the unglamorous work that’s required to win—build the state’s next great Democratic dynasty?

By Adam Reilly | Boston Magazine |
doug rubin

Photograph by Scott M. Lacey

It’s May 1, the morning after the primaries in the race for John Kerry’s old Senate seat, and the lobby of the Omni Parker House is packed with sleep-deprived, overeager Massachusetts Democrats. Ed Markey just topped his fellow congressman Stephen Lynch in a race filled with questionably sincere professions of admiration and respect between the candidates. Now, in a hallowed ritual, the Democratic establishment has turned out to show, with extra-wide smiles and extra-loud greetings, that any intramural bad blood is already forgotten.

The function room next door to the lobby is a welcome sanctuary from the forced cheeriness. In a few minutes, Markey, Lynch, and other Democratic bigwigs will take the stage, but for now, the floor is nearly empty. There are a handful of journalists milling about, along with a few antisocial Democrats—and, unexpectedly, consultant Doug Rubin, who is the closest thing Massachusetts Democrats have right now to an indispensable man.

Rubin’s ascendance began in 2002, when he mapped out a path for Tim Cahill, a former Quincy café owner, to become state treasurer. A few years later, he helped launch the political career of Deval Patrick and became his right-hand man. Last fall, he reached new heights, shepherding Joe Kennedy III, the Kennedy clan’s political heir apparent, into Congress while also calling the shots for Elizabeth Warren as she drummed Scott Brown out of the Senate.

At this moment, though, Rubin doesn’t look the part of kingmaker. As the keyed-up crowd drifts in from next door, the 45-year-old hovers on the margins, his expression inscrutable. With his perennial tan, slicked-back gray hair, and angular face, he’s a striking physical presence—but he carries himself with a gentleness that’s almost delicate. The best-known political consultants seem to swagger through the world: Think of the dandyish Democrat Bob Shrum, or the insufferably cocky Romneyite Stuart Stevens. Here, Rubin looks genuinely introverted—like he’s hoping no one notices him at all.

Then John Marttila, Markey’s longtime adviser, approaches and murmurs in Rubin’s ear—and Rubin’s whole affect changes. Smiling broadly, he places himself at Marttila’s service. “You tell us—whatever you need!” Rubin says. “Licking envelopes—whatever you need.”

Of course, as everyone in the room knows, the remark is absurd—Rubin’s envelope-stuffing days are clearly gone for good. Yet there’s something apt about his offer, because he knows firsthand how important every facet of a campaign is. Whether it’s dispatching volunteers to a particular neighborhood, or keeping the media at bay until the right moment, or distilling a candidate’s message into one memorable phrase, he’s become a master of playing the right key. But Rubin has another set of strengths, more subtle and psychological, that are just as valuable to his candidates. His method defies easy description, but it works. And we’d better understand it, since it’s shaping the future of Massachusetts politics.

FIND SOMEONE WHO’S crossed paths with Rubin over his 20-plus years in politics, and they’re likely to lavish him with praise. Governor Patrick describes his relationship with Rubin as a “blessing.” Cahill insists that if Rubin had run Ohio for Kerry in 2004, Kerry would have become president. Even Peter Flaherty, the Republican consultant who’s played key roles in the campaigns of Mitt Romney and Scott Brown, dubs Rubin a “good man.” And David Axelrod—whom Rubin hired to run Patrick’s media operation in ’06, back before Barack Obama’s two presidential victories made Axelrod a household name—calls him “incredibly shrewd and insightful.”

But Rubin doesn’t enjoy talking about himself. This spring, after reluctantly agreeing to be interviewed for this piece, he escorted me through the spacious new Government Center offices of his consulting firm, Northwind Strategies. Rubin’s political success has attracted a bevy of deep-pocketed private-sector clients, including the Boston Beer Company, Deepwater Wind, the Massachusetts Association of Health Plans, and the gaming company Gtech. “Just so you know, this is the first time I’ve done this, so…” Rubin said, wincing, as we reached his office. “I’ve steadfastly tried to avoid this throughout my career.”

Rubin’s early years offered scant hint of his future vocation. He was raised in Natick and attended high school there, playing goalie on the soccer team and doing well enough academically to get into the University of Pennsylvania. His family was an established force in the spirits business: For four generations, the Rubins have owned and operated Ruby Wines, one of New England’s major liquor distributors. When Rubin graduated from Penn, where he’d majored in political science and economics, in 1990, it was expected that he’d work in the family business.

Rubin had other ideas, but they weren’t especially focused. “I really was not sure what I wanted to do,” he said. “I had no idea to go into politics.”

So he launched a somewhat aimless job search—and lucked into a volunteer job working on Joe Kennedy II’s 1990 Congressional campaign.

“They were very welcoming, giving somebody who was brand new all this time and attention,” Rubin says, adding that he “literally did anything they asked me to do. I got to go to a lot of the events, and see some of the really good people in this business—how they conduct themselves, and how the congressman conducted himself. Learned about advance and field and about how the candidate moves around—all those things that are really part of a modern campaign.”

Rubin was hooked, and just a year out of college began running a campaign on his own, helping Cambridge City Councilor Jon Myers win reelection in a tough race in 1991. In 1992, when Dianne Wilkerson prevailed in an epic state Senate primary, Rubin was her field director, mobilizing her voters in inner-city neighborhoods that weren’t much like Natick at all. But Rubin says his background never became an issue. Instead, he learned that voters don’t want to be taken for granted, regardless of race or class—and that courting them in person is incredibly effective. “It was really the first time I had seen kind of a real massive grassroots ­operation,” Rubin recalls. “I remember specifically the number of people who said, ‘You know, nobody ever asks me to get involved and vote anymore.’”

After Wilkerson won the general, becoming the state’s first female African-American senator, Rubin joined her as a legislative aide. But he left after several months—the State House, he says, “never felt that comfortable.” Around this time, he worked briefly at Ruby Wines, and crossed the family business off his list of options once and for all. Then Rubin took a major leap: He moved to San Diego to do field work with Richard Ybarra, a political consultant and community organizer. Ybarra was involved in everything from Democratic electoral politics to organizing farm workers. He recalls Rubin as quiet and industrious, a hard worker who, perplexingly, didn’t like guacamole. For his part, Rubin remembers brutally long hours—and an epiphany about what politics could be.

“The Wilkerson campaign was grassroots organizing for a campaign to win an election,” Rubin explains. “The work with Richard out in San Diego was grassroots organizing to improve people’s lives…. It really showed me that the stuff that I do in politics can have a real impact on people, and really kind of made me feel good about what I was doing.”

Within a year, Rubin returned to ­Massachusetts and continued to establish himself, professionally and personally. Just before leaving for California, he’d started dating a girl named Stacy Kaufman—they had met on a blind date arranged by their mothers—and the pair married in 1995. (They now have three daughters: Jordan, 14, Skylar, 12, and Olivia, 8.) Soon after, Rubin got a master’s in public policy at Harvard’s Kennedy School, where his thesis, on electing minority candidates in majority-white districts, won an award.

As the ’90s progressed, Rubin racked up some impressive victories as a political consultant. One client, Paul Tavares, became Rhode Island treasurer, the first Latino elected statewide there. But there were big losses, too. He fell short in the 2001 Ninth Congressional District primary, watching his client, Brian Joyce, lose to Stephen Lynch. And in the 2001 Boston mayor’s race, Rubin worked for challenger Peggy Davis-Mullen as she was crushed by incumbent Tom Menino.

A decade into his political career, Rubin looked, if anything, like a midlevel player in Massachusetts politics—effective enough, but not destined for greatness. Then he met Tim Cahill.

 

DURING OUR INTERVIEW at Northwind, Rubin described himself as a communications middleman—someone who figures out what the public’s concerns really are and helps his clients address them with maximum efficacy. But according to Cahill, when he ran for the treasurer’s job in 2002 there was much more to it than that.

For the past decade, Cahill’s election in that race has been widely viewed as a fluke. It was driven, skeptics claim, by a ­notoriously cheery ad in which Cahill’s then-10-year-old daughter, Kendra, chirped, “Vote Tim for Treasurer!” If Kendra hadn’t concocted that line one day while doing her homework at campaign headquarters, the thinking goes, Cahill probably would have lost.

But Cahill suggests that his victory had as much to do with his bond with Rubin. As he tells it, he ran for treasurer with a hefty chip on his shoulder. There were two better-known, better-­connected candidates in the race, and Cahill felt the establishment had written him off. Rubin, Cahill tells me, felt the same way.

“Nobody wanted either one of us back then,” Cahill says. “Nobody thought I had a chance, and he was coming off a little bit of a down run. It was like two abandoned puppies that meet on a street corner and say, ‘I don’t have a family. You don’t have a family. Let’s make ourselves a family!’ And we did.”

That connection made Cahill especially receptive to Rubin’s tactical insights. Channeling his experience from the Wilkerson campaign, Rubin pushed Cahill to canvass relentlessly at obscure Democratic shindigs across the state. Sometimes Cahill felt certain stops were a waste, but he went anyway.

What’s more, Rubin distilled the essence of Cahill’s candidacy into one obnoxiously effective earworm of a phrase. He wasn’t just Tim for Treasurer, but, “A proven treasurer for treasurer: Tim for Treasurer.” Eight words, gratingly easy to remember, but also making a legitimate point: As Norfolk County treasurer, Cahill had a qualification his opponents lacked. “One of his skills,” Cahill says of Rubin, “is maybe not creating the language—but making sure you simplify it. And then repeat it, over and over.”

And that ad that helped Cahill win? It was almost wasted. Heading into the campaign’s home stretch, Cahill was short on cash and knew the ad wasn’t getting enough airtime. To buy Kendra’s spot the broadcast time Rubin said it needed, Cahill would have to dip into a $75,000 home-equity loan he’d taken out when his first daughter started college. He hated the idea—but he knew the ad was polling well. And early on, Rubin had convinced him that TV would propel him to victory.

“I was eyeing that $75,000 the whole month of August,” Cahill recalls. “I kept promising Doug, ‘We’ll have it!’ I didn’t have the guts to tell him we didn’t have it, and I didn’t have the guts to tell my wife we wanted the money.”

Rubin, Cahill says, didn’t push him. “Doug was good,” he says. “Some consultants will tell you to mortgage your house and put the money in, because then they get paid. To his credit, Doug didn’t.”

And then, with his candidacy hanging in the balance, Cahill made the tough choice he knew his newfound brother in arms wanted him to make. The most impressive part? Rubin didn’t even
have to ask.

Subsequently, Rubin took a job as Cahill’s number two at the treasurer’s office, but again grew restless. In 2004, Rubin took leaves to work for Kerry’s presidential campaign in Iowa and Ohio. After returning to the State House, though, his itch for the campaign trail didn’t abate. In 2005, Rubin went to his boss and said he wanted to do some work for another candidate. It was some guy, Cahill says, “that we’d never heard of.” His name was Deval Patrick.

doug rubin

Photograph by Scott M. Lacey

THE FIRST TIME he met Patrick, Rubin says, he was intrigued, but not quite smitten. The two spoke for a couple of hours one Sunday afternoon in the spring of 2005, as Patrick weighed a seemingly quixotic challenge to Tom Reilly, the attorney general and presumptive nominee for governor. Patrick, Rubin recalls, wasn’t interested in technical considerations, like whether he could raise enough cash to compete. His concerns were loftier: which issues really mattered to voters, say, or what the experience of running for governor would actually be like. ­Interesting guy, Rubin thought afterward. But he probably doesn’t have a chance.

A few weeks later, Patrick asked Rubin to join him on a drive to New York State, where he was giving a speech at a military base in honor of the Buffalo Soldiers. En route, Rubin was impressed yet again by Patrick’s highbrow take on the race. After they reached their destination, he watched with mounting awe as Patrick silenced a noisy room with his trademark rhetorical skill.

“He had that room mesmerized,” Rubin says. “I remember walking out of there thinking, Wow. I mean, this is something special. We drove back, and I got back to Cahill’s office that next week, and I was thinking, Man, I could be totally nuts, but I really think there’s something to this.”

But when Patrick asked Rubin to be his campaign manager, he declined, citing his father’s battle with leukemia. Patrick hired instead a grassroots maestro named John Walsh, though Rubin and the candidate agreed to stay in touch.

Early on, Patrick’s campaign put a premium on courting the Democratic grassroots. But it was also spending money at a brisk clip, and struggling to gain traction in the polls. With critics questioning the campaign’s viability, as summer turned to fall Walsh suggested bringing in someone to size up the operation—and Patrick chose Rubin.

After ranging freely through Patrick headquarters over several days, Rubin gave Patrick his assessment. More fiscal discipline was needed. So was a shift in media strategy, with less focus on the Boston market and more on regional outlets that could help build grassroots enthusiasm statewide. But Rubin’s overall prognosis was favorable: If Patrick was patient, he could win.

A few weeks later, Rubin made his connection to Patrick ­official, leaving the treasurer’s office and signing on as Patrick’s senior strategist. “Most people thought I was crazy,” Rubin says now. Of course, Rubin had insider knowledge they lacked—which made his move shrewd, as well as bold.

With Rubin onboard, Patrick gained momentum, crushing Reilly and businessman Chris Gabrieli in the primary and Republican Kerry Healey in the general election. Today, the governor says that Rubin’s biggest contribution to that first campaign wasn’t any single tactic or strategy—it was psychological.

“He understood that I didn’t want to be made into something I wasn’t,” Patrick says. “I wanted to run based on my own convictions, and the case that I wanted to make, and I wanted to build a campaign around that. And I have come to learn it’s unusual for political consultants to work with campaigns that way.”

With Patrick elected, Rubin planned to return to political consulting. But soon his friend was calling again for help. Patrick was off to a disastrous start as governor, being ripped publicly for his seemingly lavish tastes while also grappling privately with his wife’s depression. Three and a half months into Patrick’s term, Rubin agreed to join the administration as the new chief of staff—and while the self-inflicted wounds didn’t cease altogether, they became far less frequent.

When I pressed Patrick for key insights or advice he received from Rubin, I thought he might mention those rough first few months. Instead, he flashed back to a mid-2009 fight with the legislature. Patrick was battling to win major reforms on several huge issues: ethics, pensions, and transportation. He also wanted a hike in the gas tax. The legislature, meanwhile, pushed back on that reform agenda while staunchly opposing a gas-tax increase, preferring to raise the sales tax instead.

When he suggested he might be open to some horse-trading, Patrick told me, Rubin played Cassandra, telling Patrick he’d fail to get his reforms and imperil his reelection bid. In the end, Patrick ignored the advice and struck a deal with the ­legislature, ­effectively agreeing to a sales-tax hike (instead of gas) in ­exchange for two of the three reforms he wanted. The governor emerged politically unscathed. In other words, Rubin was wrong. So how is this an example of Rubin’s efficacy, exactly?

“I think it’s to the point about Doug letting me be me,” Patrick said. “He’s very, very good about laying out the options—in campaigns, in particular—and the probable political consequences of those options, but never saying, ‘This is what it takes to get elected.’ It’s always about what feels right, and what doesn’t feel right. And that’s made a huge difference for me.”

While Patrick prepared for his reelection run, Rubin took some time in the private sector, working for the private-equity firm Fireman Capital Partners. He also made a rare political misstep. In the 2009 Democratic primary fight to replace Ted Kennedy, ­Rubin’s chosen client, venture capitalist and ­Celtics co-owner Steve ­Pagliuca, finished last. Critics wondered if Rubin had taken on the political neophyte (and one-time Mitt Romney contributor) just for some quick cash, a claim Rubin fervently denies. But Patrick’s 2010 campaign provided a chance for immediate redemption.

With Rubin back as senior strategist, the governor coasted by Republican Charlie Baker, who was supposed to give him a tough fight. Along the way, Patrick turned Rubin’s former boss Cahill—who was running as an independent, and polled well early on—into a nonfactor. Cahill still marvels, with a mix of bitterness and admiration, at Patrick’s decision to lavish him with praise while Republican surrogates for Baker ripped him in TV ads. By taking the high road, Cahill says, Patrick looked likable—while Baker came off as the bad guy and saw his poll numbers drop. “I know that was coming from Doug,” Cahill says. “And it was brilliant.”

 

RUBIN HAS LEVERAGED Patrick’s two wins expertly. And while Rubin says Northwind Strategies’ focus is becoming more corporate, Rubin himself remains the hottest political consultant in Massachusetts. Exhibit A, of course, is Senator Elizabeth Warren. When Warren was first weighing a challenge to Scott Brown, she told me, she was deeply anxious about entrusting her campaign to someone who might, as she put it, “lead me in the wrong direction.”

Warren was referred to Rubin by Axelrod, who endorsed him as a “good man” (there’s that phrase again). After they spoke by phone, Rubin flew down to Washington, DC, to meet with Warren and her husband at their apartment—at which point, she says, she decided she would run only if Rubin agreed to work for her.

That’s quite a decision to make based on two conversations. But given Warren’s fear that politics might force her to be someone she wasn’t, it makes perfect sense. As with Patrick, Rubin convinced Warren that she could run, and win, without betraying her core beliefs. Even better, he promised that those beliefs wouldn’t be relegated to the margins. Instead, they’d drive her campaign.

“It was a perfect match,” Warren says. “This wasn’t about, ‘You’ll do X in the gateway cities, and Y in western Mass.’ It was about what the Senate race would fundamentally be about—and it would be about a choice between my values and Scott Brown’s. And that would be, for me, the only reason I’d get in this race.”

Naturally, Rubin offered tactical insights as well. Warren’s reliance on a few simple catch phrases—“The middle class is getting hammered!” and “Whose side are you on?”—evoked the linguistic discipline he foisted on Cahill in ’02. What’s more, early in her run, Warren kept the frustrated Boston media at bay while relentlessly wooing the Democratic grassroots. That approach echoed the communications strategy Rubin had developed for Patrick in ’06—and according to Walsh, who is stepping down this month as head of the Massachusetts Democratic Party, it was brilliant.

“While all you guys were bitching,” Walsh says of the media, Warren was courting activists “in their living rooms.” The message, Walsh says: “She cares about me.”

“And they loved her,” he continues. “To this day, they’d run through a fire for her. And Doug was getting this stuff.”

When I asked Rubin about the great failure of Warren’s campaign—her inability to dispel the festering controversy over her claims of Native American ancestry—he acknowledges he could have handled it better. Through it all, though, Warren recalls Rubin’s laughably repetitious advice as being key to helping her persevere. Be yourself, he told her—again and again and again.

“After a while,” Warren says, “I’d say, ‘Jeez. C’mon, Doug, you got any advice?’” She pauses. “That was a joke,” she adds. “But it was literally the same advice all the time. He said, ‘Go be who you are, and if people know who you are, then they can make the right decision,’” Warren recalls. “And he was right.”

IT’S A SWELTERING SUNDAY in June, and Felix Arroyo is standing near the entrance to Villa Victoria, the South End housing project where he grew up. Dressed in a shirt and tie despite the heat, Arroyo is sweaty and exultant. He’s just finished his official campaign kickoff, and hundreds of his supporters are still basking in the afterglow, exhilarated at the prospect of electing Boston’s first Latino mayor.

Arroyo still has miles to go before he can get there, but he’s already won at least one contest: the so-called Northwind Primary. Rubin is so in demand that close to half of Boston’s 12 mayoral candidates tried to enlist the help of him and his team. Arroyo is the lucky winner. Watching him at Villa Victoria, it’s easy to see why: Arroyo is charismatic and, thanks to his years as an organizer for SEIU Local 615, adept at grassroots politics. Like Warren and Patrick before him, he’s a progressive candidate who should thrive electorally in communities of color.

Of course, Arroyo is hardly a shoo-in. As one of 12 candidates, he faces dauntingly long odds—and there’s doubt that he can raise enough money. As ever, though, Rubin’s decision to join Arroyo’s campaign was shrewd: If he wins, Rubin will look like a genius. But if he doesn’t, defeat in such a big field will be relatively easy to explain away.

Rubin’s decision to shake up the 2014 governor’s race carries bigger risks. Many people had assumed he would follow ­political-consultant protocol and work with state Treasurer Steve Grossman, who hired Rubin for his successful 2010 campaign and has coveted the corner office for years. But now Rubin and Grossman have parted ways in what Rubin insists was an amicable split. “Both he and I just kind of decided that it was better for him to move in a different direction,” Rubin says.

And, perhaps, better for Rubin as well. Over the summer, rumors swirled among Boston’s political set that Rubin would work for the gubernatorial campaign of Dan Wolf, the state senator and Cape Air founder and CEO. In a field of prospective candidates that’s packed with political insiders, from Grossman to Attorney General Martha Coakley to Congressman Michael Capuano, the witty and charismatic Wolf has an appealing private-sector background and—key for Rubin—a knack for injecting values into political discourse.

But in early August, the State Ethics Commission ruled that Wolf’s stake in Cape Air and the company’s business with Massport constitutes a conflict of interest that makes him ineligible to run for governor. (After we published the print edition of this story, Wolf announced that he would suspend his campaign and resign from the Senate.) Rubin, for his part, stressed that he’s yet to commit to a candidate.

When he does—whether it’s to Wolf or someone else—we’ll know what to expect. Rubin’s gubernatorial choice will court the Democratic grassroots with obsessive zeal, honing his or her candidacy at under-the-radar events across Massachusetts with a pitch that blends wonky policy talk with moral exhortations. Slowly but surely, the campaign message will be distilled into a handful of catch phrases you can’t forget, even if you want to. The media won’t be frozen out—but it’ll get less ­attention than the volunteer army ­Rubin’s candidate is assembling around the state. And when the candidate feels frustrated—discouraged by low poll numbers, perhaps, or angered by bad press—Rubin will ease the pain. You’re running for the right reasons, he’ll say. Be yourself, stay the course. It worked for Governor Patrick and Senator Warren—and it’ll work for you, too.

 

WHEN RUBIN AND I sat down at Northwind’s headquarters, the space around him looked and felt unsettled. The firm had recently moved from a nearby office half the size, and the smell of new carpet lingered. Other than an oversize chessboard near the front entrance—an object that, for obvious reasons, Northwind has turned into a sort of informal icon—there were few decorations of any kind.

The walls in Rubin’s own office, though, were already decked out with relics that traced the course of his career. There was a black-and-white “Tim for Treasurer” poster, front pages celebrating Patrick’s nomination in 2006, an Elizabeth Warren sign from last year’s race. Most striking, perhaps, was a framed note written by Patrick in January 2007, the first month of his ­governorship. “Dear Doug,” it read. “Thank you for anchoring our team, for your strategic vision, and for your friendship. What an extraordinary movement we built, none of it possible or as vital without you.”

Rubin has focused lately on growing his list of corporate clients, and his high-­powered wall decorations deliver a clear message to any executives passing through his office these days: He is connected. In 2012, the firm’s lobbying revenue totaled $623,000, according to state filings. And Rubin says that total revenues are growing by 50 percent annually. If he manages to elect Patrick’s successor, there’s no telling how big those numbers could get.

Of course, all this private-sector success has the potential to undercut the idealism that’s become Rubin’s political calling card. After helping Grossman become treasurer in 2010, for example, Rubin signed on as a lobbyist for the gaming firm Gtech. The company has lucrative contracts with the state lottery—which Grossman now oversees. While Rubin told the Globe that he’d never lobby Grossman on Gtech’s behalf, the move felt a bit like what Patrick, during his first run for governor, derisively dubbed “Beacon Hill business as usual.”

But Rubin insists that his dual allegiances—to the politicians he’s elected, and to the corporate clients he represents—can be reconciled with a clean conscience. When it comes to lobbying the Patrick administration, for instance, “We wouldn’t take on any client if they weren’t advocating something the administration was already supportive of,” he says.

The good news for Rubin and his colleagues is that there are plenty of deep-pocketed industries—healthcare, renewable energy, gaming—whose private interests jibe with prevailing Democratic policy in Massachusetts today.

The better news, for Rubin at least, is that the Northwind Strategies office seems secure in its place as one of the state’s ultimate hubs of power. Politicians campaign for the right to be a Northwind candidate, and the corporate clients follow them through the door, knowing influence when they see it. It’s not necessarily what springs to mind when you hear the phrase “grassroots politics,” but it’s a hell of a system. And Rubin built it himself, from the ground up.

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