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.Continued...