Clean Sweep: Doug Rubin

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.