On the trail, Mike Ross looks to lend a helping hand

It was impossible to miss Mike Ross at St. Cyprian Episcopal Church in Roxbury, a 6-foot-tall white man in a bright tie and tailor-fitted suit sitting among the 75 or so black worshipers, listening attentively.

As soon as the final note of the closing hymn sounded on Sunday, he raced to the back of the sanctuary to catch worshipers as they filed out, often spending more time trouble-shooting their problems than asking for their votes.

“We’re going to figure this out,” Ross, 41, told an 87-year-old grandmother from Roxbury who was struggling to understand housing regulations at the home where she lives with a grandchild. His fingers glided rapidly over BlackBerry keys as he e-mailed a member of his City Council staff with instructions to investigate further.


Almost invariably, Ross’s campaign-trail conversations follow a similar pattern, quickly shifting from a plea for votes in the preliminary mayoral election on Sept. 24 to a discussion of how he can help them.

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Not how he can help them when he is elected. How he can help them now.

Many Ross supporters share similar stories: Their business was going to have to close, their son was going to be kicked out of their home, or their building permit was in a state of limbo — and then they called Mike Ross.

“Without Mike Ross, we wouldn’t be here anymore,” said Greer Toney, who runs Chez Vous Roller Skating Rink in Dorchester, a neighborhood institution that opened in 1932.

A few years ago, after the rink fell behind on its utility bills, Toney made a series of unsuccessful calls to city officials.


Finally, she reached Ross, then City Council president, and by the end of the day he had worked out a deal to allow the roller rink to pay down its debt and keep the lights on.

“Some people want a feather in their cap,” Toney said during a back-to-school event the rink co-hosted with Ross, who was playfully rollerskating behind her with a group of children as she spoke. “He did it because the need was there.”

Ross is convinced one of the primary underlying problems in the city is that it’s too convoluted for residents to get help when they need it. From permitting to housing, it almost always takes a call to a politician or a connected insider to get things handled — which is not an option for most residents.

“You shouldn’t have to know a politician to get things done in this city,” Ross often says.

That passion for equality, he says, is a product of his upbringing.


His father, Stephan, is a retired psychologist, longtime city worker, and Holocaust survivor who founded the New England Holocaust Memorial, which former Boston mayor Ray Flynn, a friend, describes as “a living symbol of who we are and what our values are as a people and city.”

But it was a kitchen conversation with his mother in 1984 that perhaps shaped his worldview just as much as years of hearing his father discuss the horrors of Nazi concentration camps. When he was 13, his mother sat him down in their modest home behind the neighborhood grocery in Newton to tell him she was a lesbian.

He admits that, as a teen who was trying to fit in, he was initially shy about his mother’s sexuality. But, Ross says, growing up in a blended family that included his mother’s new partner forced him to value equality from an early age.

“You can’t grow up in that environment — with a father imparting stories from the Holocaust and a mother living in an openly lesbian relationship — and not pick up some values along the way,” said Ross, who would be Boston’s first Jewish mayor if elected.

After high school, Ross shipped off to Clark University, where he ran an upstart campus pizza shop, before returning to Boston to get his MBA from Boston University and a law degree from Suffolk University.

But his real desire was to get involved in city government, which led him to apply for a job helping to run the city’s website during its infancy.

Ross’s job was to put photos of Thomas M. Menino on the home page, and he eventually developed a mentoring relationship with the mayor, who soon hired him as an aide.

Before long, Ross was hooked and in 1999 decided to run for the District 8 City Council seat, representing the Back Bay, Beacon Hill, and Mission Hill. Navigating his blue Volvo through Roxbury, Ross recalled that first campaign.

“Honestly, I really shouldn’t have won that race,” he said.

Through shrewd political maneuvering, grass-roots campaigning, and dumb luck, the 27-year-old City Hall worker operating out of his tiny basement apartment in Beacon Hill somehow defeated Suzanne Iannella, the next in line from a dynastic clan of Boston politicos.

She had raised five times as much money.

Now, almost 14 years later, Ross finds himself in what seems like another uphill battle. Although he is one of the better-funded candidates, with $435,000 cash on hand coming into September, most polls show Ross somewhere in the middle of the fluid 12-candidate field in which no one has yet emerged as a front-runner.

The Ross campaign has focused on racking up endorsements and appearing at community events for most of the summer while stockpiling its money for a large-scale television advertising buy in the race’s final month — in the hopes that the bulk of the so-far uninterested electorate starts tuning in.

On the campaign trail, Ross can often be awkward as he first approaches potential voters, but his delivery becomes more smooth as he turns the conversation to his council work. Often, he will cite various council resolutions, and the fights to get them passed, as examples of how far he has come since he was elected a decade and a half ago.

He most often harkens back to the council’s 2011 clash with the firefighter’s union.

An arbitrator had ruled in favor of a settlement that included a 19 percent pay increase for firefighters that would have forced the city to close libraries and lay off employees.

Ross publicly opposed the pay increases and helped to broker a compromise.

“I went to the union leaders, had a few Bud Lights, and we were able to figure out something that kept us from having to close those libraries,” Ross said.

His campaign often brands him as an “innovation candidate,” and Ross likes to highlight that he was the driving force behind the Night Owl, a short-lived initiative that provided public transportation until 3 a.m.

If elected mayor, Ross vows, late-night MBTA service will return next year.

Meanwhile, his campaign speeches often focus on the need to work better with other governments in the region, such as Cambridge and Somerville, to attract more businesses to Greater Boston.

Above all, Ross says, the city must be willing to look to other cities for best practices, such as when he passed a resolution for more dog parks in the city or traveled to Los Angeles to research the food truck industry, which is now flourishing in many parts of Boston.

It is achievements like those that he stressed while door-knocking in Jamaica Plain on a recent Saturday afternoon.

“Can I ask you one question?” Barbara Wicker, called out to Ross as he was walking away after a 15-minute chat.

“Why do you want to be mayor?”

Stopping in mid-stride and turning to face the potential supporter, Ross responded quickly.

“Because,” Ross said, “I think I can make a difference.”

Wesley Lowery can be reached at Follow him on Twitter @WesleyLowery.