Daniel Winslow cuts an independent path

Daniel B. Winslow has served in all three branches of state government, including as a judge in Wrentham District Court.
george rizer/globe staff/File 1999
Daniel B. Winslow has served in all three branches of state government, including as a judge in Wrentham District Court.

Representative Daniel B. Winslow likes to eat Marshmallow Fluff, the made-in-Massachusetts confection that makes up in sugary nostalgia what it lacks in nutrition. But that is not why Winslow left 10 tubs of Fluff stacked in a pyramid outside the office of Governor Deval Patrick’s budget director in December, a red bow on top.

Patrick had just proposed fixing a deficit partly by cutting aid to cities and towns. Winslow objected and was certain he had better ideas to offer. Nobody however “reads six-page, single-spaced letters in state government,” especially from a freshman Republican, he explained later. So he affixed his ideas to the marshmallow props, invited reporters along for the delivery, and tweeted every step of the way. When his Fluff was rebuffed by the administration, he gave it to charity, tweeting about that, too.

John Tlumacki/ globe staff/ file 2012
Daniel Winslow is banking on his experience and moderate social stances to win over voters.

“I’ve been kicked out of better places than the governor’s budget office,” he later quipped.


The episode was classic Winslow, who brings to his current campaign for Senate not just an unusual resume — having served in all three branches of state government — but a reputation as both an ideas person and a showman.

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Unquestionably bright and eminently quotable, Winslow is now trying to convince voters that he is the right fit to replace John F. Kerry in the Senate.

As a judge and a Norfolk town official, as the top lawyer for Governor Mitt Romney’s administration, and now as a GOP representative in a Legislature dominated by Democrats, the 54-year-old Winslow, a married father of three, has won honors for innovation and drawn an outsized share of media attention.

thomas landers/ globe staff/ file 1990
Early in his political career, Winslow was a member of the Norfolk Planning Board when his home was firebombed by an angry developer

Admirers see him as a rare policy wonk with a glint in his eye, able to think big, dive deep, and sell serious ideas with ebullience. Skeptics, especially in the state Legislature, see him as a self-promoting maverick, too clever by half.

In 2007, Massachusetts Lawyers Weekly named him one of the 35 most influential bar members of the previous 35 years, for his effort to remake the judiciary as Romney’s top lawyer. The designation landed him alongside touchstones such as Governor Michael Dukakis and W. Arthur Garrity Jr., the judge who ordered busing to desegregate Boston’s schools.


Winslow’s frenetic first term in the Legislature prompted the nonpartisan Governing magazine to name him in 2012 one of “12 State Legislators to Watch” nationally.

wendy maeda/ globe staff/ file 2004
Winslow later served in Governor Mitt Romney’s administration.

This is the same Winslow who held a “beer pong” fund-raiser — albeit with water — to attract millennial Republicans, hired his own private detective to investigate a controversial Patrick administration nominee, and weighs in as a regular commentator on the true-crime current affairs show “Nancy Grace.”

Particularly unfiltered on Twitter, Winslow has likened Massachusetts House Speaker Robert DeLeo to a North Korean dictator and riffed that US House leaders from both parties in Washington needed “psychotherapy or an enema” for failing to compromise on a payroll-tax dispute, addressing them, “Dear Idiots...”

In the first debate for the three Republican primary candidates, Winslow arrived dramatically late — “We hear you’re looking for a candidate,” he joked, breezing through the lobby — and landed the most one-liners.

When the moderator cited the Fluff incident and asked whether his “out-of-the-box theatrics” make him a poor fit for the often-staid Senate, Winslow didn’t bristle so much as embrace the question.


The Fluff, he said, was not a gimmick but a means to an end, noting that Patrick’s budget chief later sent him a note saying he would incorporate some of his suggestions. Plus, Winslow added, there should be more room for fun in the give-and-take of politics.

“I’m in the loyal opposition. My role is to poke back against and speak truth to power, and I intend to do the same thing down in Washington,” he said that night. He called his “theatrics” no more fanciful than the founding fathers donning headdresses and dumping tea overboard instead of writing letters.

Performance, with a purpose

To Winslow, his stunts are always in service of ideas, always in good humor. “For god’s sake, can’t we have people in politics who can take a joke or poke some fun at themselves?”, he asked in a recent interview. “Everybody’s so damn stuffy in this business.”

Eric Kriss, a Bain Capital co-founder who worked with Winslow in the Romney administration, called him an uncommon blend of optimism and tenacity, pragmatism and creativity.

“I don’t think he’s wacky for the sake of being wacky. He’s not unstable,” said Kriss, who was budget chief for Romney when Winslow was the governor’s legal counsel a decade ago. “He is trying to participate in the game of political theater in an attempt to get his views better known.”

In 2010, after winning the Massachusetts House seat once held by friend Scott Brown, Winslow vowed to serve only three terms, staged his first State House press conference before being sworn in, and filed four dozen bills as a freshman, several times the norm — raising eyebrows among some lawmakers, who questioned whether Winslow was charging toward a run for attorney general or for governor.

Instead he jumped into the Senate race after Brown decided not to run, brushing aside suggestions of opportunism.

He views the Senate special election as a chance to rebrand the GOP as a socially inclusive party focused on smaller government and free-market principles. Because Winslow has been pitching for years the need to reach out to women, minorities, and young voters — long before Romney got trounced among such voters — he considers himself the man for the job.

“Massachusetts has an opportunity to set the agenda, to set the tone, and to set the direction for our country” ahead of the 2014 midterms, said Winslow. He believes tentative economic recovery can become full-blown success, “if we can only unfetter that American spirit from the excessive burdens and crushing regulations . . . and take some of our freedom back.”

Despite being a ready quote on Beacon Hill for a decade, Winslow in March polled the lowest name recognition of any Senate candidate from either major party.

Aware that time is short in a compressed primary season to make up those numbers, Winslow has been campaigning at breakneck speed against GOP competitors Gabriel E. Gomez and Michael J. Sullivan, reminding voters in an overwhelmingly Democratic state that he offers the most moderate politics of the three. A Republican who supports gay marriage and drives an electric car, Winslow believes that if enough people hear his pitch and review his record, he’ll get the votes he needs.

The colorful character on the campaign trail isn’t a construct of political handlers, it’s who he has been since childhood, when he remembers fretting that all the good inventions had already been invented. His early creativity included painting gloves Day-Glo red and green to help traffic cops get their message across faster.

Early on, a sense of urgency

Often taken for a Brahmin, Winslow had a modest, rural upbringing, living partly in a trailer where a UMass dorm complex now stands in Amherst. His mother, the daughter of Italian immigrants, worked as a nurse. His father, who can trace ancestry to a colonial coffin-builder, fought in Korea and settled in Amherst after attending college on the GI Bill. Initially an antenna repairman, he stopped scaling towers when his sons were born.

Daniel was the first of five boys, one of whom died in infancy, an early memory seared on Winslow’s mind. That loss seems partly why his mind and body are always churning: “I don’t know how much time God gives me on this earth, and I want to get something done before I go.”

Winslow’s father eventually built a telecommunications business, mortgaging everything, his son said, after refusing to pay a kickback to a “prominent politician” dangling a public loan. The experience imprinted Winslow with a sense that government can help or harm business. It also inspired his Tufts University thesis on the corrupting role of money in politics.

Winslow went from Tufts to Boston College Law. A national mock-trial finalist, he landed a job as a litigator at a boutique firm and made a name arguing election law for the Republican Party.

He successfully challenged Beacon Hill Democrats for drawing unconstitutional legislative districts after the 1985 state census and again with congressional seats after the 1990 US Census.

“In court it was a level playing field,” he recalled. “The Democrats were just not used to a fair fight, and so they were really bad at it, shockingly bad.”

In both lawsuits, Winslow and the GOP teamed with the Black Political Task Force, initially a marriage of opportunity. But task force leader Joyce Ferriabough-Bolling said she saw in Winslow a commitment to diversity, affirmed in his later advocacy for women and people of color in Republican circles and at white-shoe law firms.

Even though she has long been a Democratic consultant, Ferriabough-Bolling praises the man she calls “my buddy Dan Winslow” and even wrote him a campaign check in 2010. “He’s shaking things up,” she said. “You may like him or dislike him, think he’s a showboat or not, but I look past that to the fiber of the guy.”

But as his name recognition was on the rise, it wasn’t always for his legal work. In 1990, while a 32-year-old member of the Norfolk Planning Board, his house was firebombed by an allegedly frustrated strip-mall developer after Winslow pushed tough but far-sighted zoning changes to preserve the town’s rural character.

Winslow started mowing his lawn in a bulletproof vest but refused to move or resign. The developer was never charged but instead ordered to keep away from Winslow for life. A Globe investigation a decade later uncovered widespread complaints against the same developer in nearby Franklin.

It was Winslow’s Republican legal acumen that won the attention of Governor William Weld, who nominated him for the Wrentham District Court bench in 1995.

Ruddy cheeked and still in his 30s, Judge Winslow earned a reputation for cordiality with lawyers, patience with jurors, and severity toward repeat offenders. He tinkered from the start, winning a national think-tank award for using a “smart calendar” to minimize unnecessary court appearances and to program the docket based on the likelihood of cases going to trial.

Winslow also printed bright-orange bumper stickers to brand the cars of recidivist drunk drivers and ask motorists to report erratic driving, but he abandoned them after a test on his own Volvo, amid a torrent of criticism from civil libertarians and defense lawyers.

A chance to remake judiciary

At 44, Winslow walked away from the robes, job security, and pension to join the newly elected Governor Romney in 2002, determined to have a larger impact on the state’s judiciary.

Romney agreed with Winslow’s assessment that the judiciary was a haven of waste and cronyism, giving him freedom to revise the nominating process for judges, emphasizing blind resume reviews and curbing a pattern of politicking by candidates. Winslow also set in motion a shift to funding local courts based on case load, not the whims of Beacon Hill.

Many Winslow plans, however, ran aground with the Legislature and the unions. He clashed in particular with advocates for the poor. Critics found him to be a smart-aleck but admired his accessibility.

He tried unsuccessfully to close some courthouses and centralize the hundreds of lawyers dispersed among state agencies in a streamlined office.

“Some of that energy and some of that type of effort took some folks off guard,” said Martin W. Healy, general counsel for the bar association, today a Winslow admirer. “People weren’t prepared for a legal counsel to be as active.”

Several top officials from the Romney years said the data-driven Winslow was as much an all-around adviser as lawyer to Romney.

Romney endorsed Winslow’s desire to return to the bench but backed down from an ugly confrontation with the Governor’s Council, some of whom saw Romney and Winslow as smug outsiders.

“They feel they are better than us,” Councilor Christopher Iannella said at the time.

So Winslow took a lucrative law firm job instead and sought public office at a lower level, running successfully for Norfolk moderator with a plan to boost town meeting participation through door prizes, music, and free food.

Historic win brings a chance

The shuffle after Brown’s Senate win created an opening for Winslow to run for the Massachusetts House, after the local state representative advanced to state Senate. Winslow rubbed some new colleagues the wrong way when he refused to accept per diem mileage payments and described the House as a stale club “desperate for ideas.” Some veterans say he has flitted among issues — labor relations and ethics reform, high-speed tolling and cigarette pricing — more for attention than results.

He’s “like a bee going for the pollen and then moving to the next flower and not bothering to come back,” one senior Democrat said.

Winslow faults the Democratic speaker for sidetracking many of his proposals but points to successful measures he authored, including one to adopt a national standard for defining “intellectual disability” in place of arbitrarily strict state regulations that he said barred some deserving people of benefits.

Winslow said that he is better equipped to compromise in the US Senate than his GOP opponents — where they want to repeal Obamacare, he proposes fixes — and that as a judge and politician he has mastered patience and humor without shying from a fight.

He’s sure that brand of socially liberal, fiscally conservative politics, combined with his unflagging energy, is the best way to attract independent voters beyond the primary in Massachusetts.

But without the name recognition that Sullivan enjoys, or the wealth and personal story that Gabriel Gomez leans on, Winslow acknowledged he’s not getting the traction he thought he would on a statewide stage.

Winslow said he just hasn’t had the time to create the buzz he’s often so good at generating. And grass-roots hustle might not be enough to get the votes he needs.

That has not slowed him down.

When I make an impression on people, I tell [them], ‘Look, if you agree with what I said, we can all be like pebbles in the pond and send out the ripples. Tell your friends and tell their friends,’’’ Winslow mused.

“And if you disagree with what I’ve had to say, we’ve never met.”

Eric Moskowitz can be reached at emoskowitz@globe.com. Follow him @Globemoskowitz on Twitter.