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?

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.”

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