“I’ve turned being an alcoholic into being a workaholic,” says Marty Walsh, who got sober more than 20 years ago.
“I’ve turned being an alcoholic into being a workaholic,” says Marty Walsh, who got sober more than 20 years ago.
Keith Bedford/Globe staff

GLOBE MAGAZINE

Marty Walsh has a confession to make

After an early crisis of self-doubt, Boston’s 48th mayor found his own way

STANDING ON THE BACK of a flatbed truck, Mayor Marty Walsh and Governor Charlie Baker fire their air horns into the June sky. That unleashes a current of more than 2,000 runners wearing bibs on their chests and buds in their ears.

The Corrib Classic 5K Road Race is a fixture on the calendar of West Roxbury. Walsh lost that neighborhood decisively four years ago in his squeaker of a victory to become Boston’s 48th mayor, and he is now standing beside the governor with the highest approval ratings in the country. So it’s surprising and perhaps telling that the name the runners keep yelling as they pass the flatbed is “Maaahty!”

At one point, as Walsh is swarmed by yet another pack of spectators angling for a selfie with the mayor, Baker looks on admiringly. The governor busies himself by mouthing the words to Journey’s “Don’t Stop Believing,” which is blaring on the loudspeaker.

After a blitz of additional pictures, Walsh dashes into the passenger seat of an idling Chevy Tahoe that will whisk him to the next event on his packed Sunday schedule. I climb into the back. The welcome the mayor just received was so enthusiastic that I am caught off guard by what he discloses next, about the early part of his term.

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“I’ve never said this to anyone,” Walsh tells me. “I literally went home every night for the first three months and said, ‘Oh, my God, what have I gotten myself into?’ ” 

He had surprised many people when he edged out city councilor and West Roxbury native John Connolly in the fall of 2013 for the right to succeed legendary 20-year incumbent Tom Menino. That was a heady achievement. But when it came to being mayor, Walsh admits he felt so overwhelmed that he started to wish he’d never won. “I couldn’t talk to anyone about it, because everyone around me helped me get elected. So I couldn’t go to them and say, ‘I’m not really thrilled about this job.’ ”

It wasn’t the grueling schedule. After more than two decades in recovery, Walsh says, “I’ve turned being an alcoholic into being a workaholic.” It was going home feeling utterly drained but worried all the hours weren’t amounting to anything. He’d lie awake asking himself, “How am I going to do this?”

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Walsh has always had a deeper well of ambition than his lunch-pail presentation suggests or than even his family and closest friends felt he was capable of fulfilling. Long before his first, improbable political win — getting elected as a state representative from Dorchester in 1997 — he’d set his sights on becoming mayor of Boston.

Now that he had the job, though, he was longing for a return to his uncomplicated life split between Savin Hill and Beacon Hill, when he was less in the limelight but more in control. As mayor, he had to contend with a city workforce that could be unwieldy, a longtime girlfriend chafing from the loss of privacy, and media scrutiny that never seemed to wane. Critics began predicting he would become Mayor One-and-Done.

Although Walsh is now approaching the end of his first term, many people still have the same three-pronged, surface impression of him that they had when he first ran: Irish-Catholic, union, Dorchester. He’s the guy with the Boston accent who lives five houses down from you, who works in construction and shovels your elderly neighbor’s walk without being asked but whom you know nothing else about. Even his City Hall office reinforces the holy trinity shorthand, packed as it is with memorabilia from Ireland, the union trades, and Boston sports.

In reality, Walsh is a much more complex and interesting character than that and one who is unusually good at converting self-doubt and others’ low expectations into the high-octane fuel he uses to thrive.

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One day in March 2014 he was sitting alone at the polished conference table in his office, staring out the window at Faneuil Hall, when a sense of calm came over him. He finally felt he was settling into the job. He realized that, to get better at being mayor, he could rely on the same approach he had used to get sober: one day at a time. For the first time, he felt confident it would all come together. He told himself, “I got this thing.”  

(R-L) Marty Walsh celebrates with his longtime partner Lorrie Higgins, her daughter, Lauren, and his mother, Mary, at his Election night party at the Park Plaza hotel in Boston, Massachusetts November 5, 2013. (Jessica Rinaldi For The Boston Globe)
Walsh celebrates with his longtime partner, Lorrie Higgins, her daughter, Lauren, and his mother, Mary, at his election night party at the Park Plaza Hotel in 2013.
Jessica Rinaldi for the Boston Globe/File 2013

CRITICS WOULD ARGUE it took Walsh a lot longer than three months to get his bearings. He spent the first half of 2015 trying to ride the unruly bronco that was Boston’s 2024 Olympics bid. The bid had preceded his election, but Walsh had given it his full support. After the US Olympic Committee selected Boston, he inherited all of its heavy baggage.

For much of that period, it looked as if the bronco would toss Walsh at any minute. Blame Olympic officials for their tone-deafness, but also blame Walsh for some rookie blunders, like signing off on a gag order that barred city employees from criticizing the bid.

Then there was the aborted plan to hold an IndyCar race in the Seaport. The out-of-the-box idea might have worked had the IndyCar organizers been ready for prime time. “Someone on my team should have picked up on the problem,” Walsh tells me. A Google search would have been a good start.

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There were also some knotty issues at Boston Latin School and other Boston public schools. Walsh’s handpicked school superintendent, Tommy Chang, arrived from Los Angeles with impressive reformist credentials. But even supporters, including Walsh, concede that the political inexperience of Chang’s team has made it harder for the reform agenda to get traction here. (Walsh’s decision to install his own guy — former city councilor Rob Consalvo — as Chang’s chief of staff means the mayor now has an experienced political hand in place to ensure there are no embarrassing school stories blowing up on the front page between now and Election Day on November 7.)

The biggest threat to the Walsh administration came last year with the indictments of two senior aides, tourism chief Ken Brissette and head of governmental affairs Tim Sullivan. The US attorney’s office alleges that Brissette and Sullivan threatened to withhold permits for the Boston Calling music festival if organizers did not hire union workers. (Prosecutors also alleged that Brissette was involved in some heavy-handed union behavior during the 2014 filming of the TV show Top Chef, although they never charged him.)

There has been no evidence presented so far to suggest wrongdoing on Walsh’s part. But the allegations fed into concerns raised during the 2013 campaign that Walsh, a former head of the Boston Building Trades Council, would be compromised in leading the city because of his previous work leading the unions. 

As one longtime City Hall observer put it, the Menino team had honed a sophisticated approach over the years for using private citizens as emissaries to communicate what the mayor expected of people with business before the city. This alleged wrongdoing by Walsh’s aides suggested a clumsy ascendancy of the unions, the fox suddenly governing the henhouse.

By now, there is wide consensus that Walsh was able to right his ship. Some suggest it happened in the fall of 2014, after Menino died, or in the summer of 2015, after Walsh walked away from the Olympic bid instead of saddling the city with potentially billions in overruns, or in the winter of 2016, when General Electric chose Boston for its world headquarters.

Whenever it happened, Walsh now finds himself in an enviable position as he revs up his reelection campaign. He says that even during the controversies, his internal polling showed his approval rating never took a hit.

One likely reason: There’s never been a suggestion in this investigation that City Hall officials were lining their own pockets. (Walsh benefited when a judge decided the trial for his aides would take place in January 2018, comfortably after the November election.)

Meanwhile, the city on Walsh’s watch has enjoyed a booming economy. Developers report being happy the new mayor has made it easier for them to get their projects approved, whether or not they supported him in the election. A persistent criticism of the previous administration was that the road to yes was unusually well paved for a small group of favored developers and all but impassable for others. “That doesn’t happen anymore,” Walsh tells me.

Another change: During the Menino administration, neighborhood civic associations could count on City Hall to quash developments they didn’t like. “That doesn’t happen anymore, either,” Walsh says. This change is particularly surprising because Walsh cut his political teeth as the head of his neighborhood association. He says he’s serious about Boston getting 53,000 new units of housing by 2030. If a plan looks good to his team, has a strong affordability component, and enjoys the support of abutters, he says, it is likely to get the nod even if the neighborhood association opposes it.

In ways big and small, Walsh and his team have opened up the windows to let fresh ideas into City Hall. (Not literally. The windows on the hulking, Brutalist mass of concrete continue to be sealed shut.)

Boston , MA - 6/9/2017 - Boston Mayor Marty Walsh meets with his staff in his office in City Hall in Boston , MA, June 9, 2017. (Keith Bedford/Globe Staff)
In scheduling meetings, Walsh’s staff figures out how to get him to as many events as possible. Chief of Staff Dan Koh sits to Walsh’s left.
Keith Bedford/Globe staff

Although Walsh has an old-school sensibility, he has surrounded himself with many young aides, who have brought a millennial, tech-savvy sensibility to city government. It makes for an interesting mix. City Hall now features flat screens and human greeters, both designed to make government more responsive. Instead of residents having their complaint calls bounced around from department to department, they can call 311, where they are promised that they’ll have contact within 30 seconds with a human who will log their concern into the computerized CityScore system. Flat screens hanging in the mayor’s office report in real time how each city department is performing in resolving these complaint calls from residents. Dan Koh, Walsh’s 32-year-old chief of staff, calls this a Moneyball approach to municipal government.

While Walsh’s Young Turks have made their share of rookie mistakes, they have also impressed people in unexpected ways. Dave Sweeney, Walsh’s 34-year-old chief financial officer, has helped the city receive AAA bond ratings for an unprecedented four years in a row. Critics had predicted Walsh would be a poor financial steward for the city because he would struggle to say no to union demands. It’s noteworthy that the city under Walsh has seen its bond ratings rise while the state, under Governor Charlie Baker and his strong business credentials, just saw its bond rating lowered.

Ironically, the biggest political gift for the mayor was the election of Donald Trump, a man who offends Walsh to his very core. It especially irks Walsh that the new president was almost surgically successful in appealing to the mayor’s kind of union-driven blue-collar base.

Nonetheless, when Trump went after immigrants and Muslims with his administration’s travel ban and environmentalists with his rejection of the Paris Agreement, Walsh converted his outrage into winning politics. The mayor who had last made the national news because of an aborted Olympic bid now found himself sitting across from Trevor Noah on The Daily Show, being cheered by a progressive audience for vowing to turn City Hall into a sanctuary for undocumented immigrants.

While his national profile has been growing, Walsh has also been working to expand his base around Boston. His staff holds a weekly scheduling meeting that feels as complicated as spinal-fusion surgery, given the choreography required to get him to every block party and nail salon opening.

When Menino ran for his fifth term, a poll showed a stunning 57 percent of Boston voters had personally met him. Walsh sometimes seems determined to hit that mark — and to somehow hustle his way there after just one term. 

THE DAILY SHOW

THE HORSES ARE GETTING RESTLESS and the smell of freshly dropped dung is wafting in the humid air. It’s the annual Dot Day Parade, and Dorchester’s current most famous son is leading the pack. Behind Walsh is a collection of police officers on horseback. To satisfy every spectator expecting a handshake or a high-five, the mayor repeatedly crisscrosses Dorchester Avenue. The saddled cops try to keep their horses in check, walking them around in small, concentric circles to avoid colliding with Walsh’s delegation in front of them or getting rammed by the bands and marchers coming up from behind.

The parade route stretches 3.2 miles along Dot Ave., the spine of a remarkably diverse section of Boston. Dressed in a white shirt and green tie, the mayor presses the flesh with older Irish ladies in wheelchairs and bearded hipster dads with babies strapped to their chests, with Haitian middle schoolers and Cape Verdean grandparents, with Chinese mothers pushing strollers and Vietnamese merchants standing outside their shops. The cheering section even includes an Ireland-born bruiser by the name of Kevin McBride, who once faced Mike Tyson in the boxing ring and somehow emerged victorious, with both ears intact.

“Thanks for standing up for the Paris Agreement!” one white female boomer calls out.

“You’re gonna win! You’re gonna win!” shouts a middle-aged black woman.

“Thank you!” the mayor responds before swallowing three syllables into one with his trademark “Howaya?”

Granted, Walsh is on his home turf, carrying with him the formidable power of incumbency. But the depth and diversity of his support along the parade route highlights just how hard it will be for the mayor’s most prominent challenger, City Councilor Tito Jackson, to dislodge him this fall. A recent Globe poll found Walsh up by 31 points. Before the marching began, Walsh gathered for group shots with other pols in Lower Mills, just around the corner from his new house on Butler Street. Right before the photographer hit the shutter, Jackson jumped into a shot. Photo-bombing remains an unproven campaign strategy.

During the parade, even when Walsh gets the rare critical comment instead of an attaboy, he has figured out how to turn it around. An older woman greets him by saying, “I’m mad at you,” explaining that her street wasn’t properly plowed during the winter. The mayor cracks: “You’re still mad about the snow? It’s June!” Her scowl fades.

The most meaningful interactions seem to be with people who can relate all too well to one part of his story. When he stretches into the crowd to shake one woman’s hand, she whispers with evident pride, “Two years sober.” A few blocks farther along the avenue, the report is less uplifting. This woman is clearly strung out. After shaking her hand, Walsh turns to an aide and requests one of his business cards.

Alcoholics and addicts all over Boston have Walsh’s personal cellphone number. Since he became mayor, his aides have pleaded with him to change that number. Walsh’s chief of civic engagement, Jerome Smith, says it can complicate the business of running city government when so many civilians have a direct line to the mayor. Walsh has steadfastly refused. If somebody desperately in need of a bed in a detox facility dials him one night, he doesn’t want that person getting an out-of-service message.

When he addressed the Democratic National Convention last summer, he caught the crowd by surprise with his opening line: “My name is Marty Walsh, and I am an alcoholic.” As he said it, he could hear giggling from the California delegation in front of him. “They thought it was a joke,” he says. They quickly figured out he was serious, and the unusually confessional nature of the speech about the importance of second chances kept the boisterous convention crowd rapt.

“On April 23, 1995, I hit rock bottom,” he said in his speech.

Over a recent lunch, oddly enough at the 21st Amendment, a Beacon Hill pub named after the repeal of Prohibition, I ask Walsh what made that April day so significant.

He’d been drinking all weekend and went to see the Bruins that Sunday afternoon. “I was asked to leave the Bruins game because I was so drunk,” he says. “I went across the street to the Harp and started drinking. I fell asleep there, and my friends had to come take me out.”

At the time, he was a functioning alcoholic. By all appearances, he was doing well at work — he was a collection agent for the union, with a union-issued car — and as a community leader, running Savin Hill’s civic association and youth baseball league. But inside, he was a mess.

He spoke with his boss, who connected him with a counselor. “The guy on the other end of the phone gave me an interview about alcoholism,” Walsh recalls. “I passed it, and I didn’t want to pass it.”

He figured he’d go to some Alcoholics Anonymous meetings and then in six months, “when the heat’s off, I’d drink like a normal person.” Instead, the counselor recommended inpatient treatment at Gosnold on Cape Cod. Life was never the same.

Walsh (right) and City Councilor Tito Jackson, his most prominent opponent in this year’s mayoral race, joined the Dot Day Parade in June in search of votes.
Walsh (right) and City Councilor Tito Jackson, his most prominent opponent in this year’s mayoral race, joined the Dot Day Parade in June in search of votes.
Neil Swidey/Globe staff

Back on the parade route, Walsh draws the most uproarious cheers when he walks by the bars on Dot Ave. — the Blarney Stone, Tom English, Peggy O’Neil’s, where tipsy patrons baking in the sun take special delight in hooting “Maaaahty.” (Walsh says it doesn’t bother him to step inside bars these days and do a bit of backslapping. “I’ll come in and buy people a round. But I’m not coming in to watch people drink for six hours.”)

Farther down Dot Ave., where it intersects with Taft Street, Walsh approaches an older woman with reddish-brown hair like his. “Howaya, Mom,” he says, bending to kiss her. This section of Dorchester — around what old-timers still call St. Margaret’s Parish, even if the church was renamed in memory of Mother Teresa — is the area Walsh knows best. “Growing up, your world was like four blocks,” he says.

Mary Walsh moved into a slate-blue three-decker on Taft Street 50 years ago, when she came home from the hospital with Martin, her firstborn. She and her husband, John, who had both emigrated from County Galway, Ireland, rented the place for a year before buying it. There they raised Marty and his younger brother, Johnny. Marty’s father died in 2010, but Mary continues to live in the first-floor apartment, with Johnny on the third floor and a cousin in between.

Marty’s father was a union construction worker who was determined that his sons get a college education and have options besides the trades. Marty had other ideas. He had been a weak student. After a year at Quincy Junior College and a semester at Suffolk University, he dropped out to make money in construction. His uncle Pat Walsh ran the union as business manager and helped his nephew get his collection agent job.

When Marty told his parents in 1997 that he was going to run for state representative, they urged him not to do it. His mother didn’t want to see him put through the wringer. His uncle saw a clearer path of advancement for him in the union, maybe even a job in Washington.

But Marty had been enamored with politics since the first time he saw his surname on a bumper sticker, as part of his uncle’s campaign for union business manager. He copied the design of his uncle’s bumper sticker for his own state rep race. He won by just 246 votes. He hasn’t lost a race since.

Now his mother is his biggest supporter, doing her part by praying for Martin — she never calls him Marty — every morning.

(Later, during a visit to her house, I ask Mary Walsh if her friends bombard her with requests for the mayor. She smiles and says no. The mayor smirks and rolls his eyes. “Really, Mom? I got a call from one of them this morning!”)

Walsh can’t stay long with his mother, because the restless horses behind him are doing doughnuts again. As he charges ahead through the next intersection, an aide points up at the sign for Crescent Avenue and says to another politician: “Oh, man, this is a fateful corner for the mayor. This is where he caught one back in the day.” What he caught was a bullet, in his leg, when he was 22, after another late night of drinking.

Boston , MA - 6/19/2017 - Boston Mayor Marty Walsh chat with his mother Mary in the family home in Boston , MA, June 19, 2017. (Keith Bedford/Globe Staff)
Walsh visits with his mom, who still lives in the Dorchester triple-decker where he grew up.
Keith Bedford/Globe staff

The parade ends at Columbia Road, across from the church and parochial school where Walsh spent so much of his childhood.

His police security detail for the day, Joe Holmes, has the SUV waiting, and after one final round of handshakes, Walsh jumps into the passenger seat to race to the next event. He grabs several pieces of the Orbitz gum that powers him through the day and flips through the leather-bound briefing book his staff prepares for him daily. Mentioning the 3-mile workout we’d just had, I ask him if he does anything for exercise besides walking in parades.

“I have one of those Fitbits,” he replies, eliciting an eye roll from an aide sitting next to me in the back seat. “My doctor wants me to get more exercise than just getting in and out of cars.” But Walsh says his grueling schedule makes that tough.

“Did you get much exercise before you became mayor?” I ask.

“Not really.”

The commencement ceremony for the older, low-income students at Urban College is already underway when Walsh passes through the stage door entrance of the Cutler Majestic Theatre, slips on his black gown, and bounds on stage.

“I know what it’s like to be in your shoes in a lot of ways,” the mayor tells the students about to receive their degrees. “I didn’t graduate until I was 40 years old. I didn’t go when I should have.”

He didn’t get serious about resuming his college studies until after he began working at the State House and was taking night classes at Boston College. There he was, a thirtysomething state representative, struggling to get it done while sitting in class with a bunch of 19-year-olds. It was frustrating and embarrassing.

“I’m now 50,” he tells the Urban College crowd, “and I’m still giddy when I look at my degree.”

Instead of serving up platitudes, the mayor connects with the crowd by emphasizing the story of struggle that he and they share. Although most of the seats are filled by people of color, he finds another source of similarity. “There’s a lot of conversations about immigrants today in America, and in some cases, it’s not a good conversation,” he says. “But in my house, it is a good conversation, because I’m proud that my parents are immigrants from another country.”

With that, the packed theater erupts in whoops and applause.

Boston , MA - 6/19/2017 - Boston Mayor Marty Walsh greets passersby who stopped to take a picture with him in Boston , MA, June 19, 2017. (Keith Bedford/Globe Staff)
A Boston family pulls over to greet the mayor as he walks the “four blocks” surrounding his childhood home in Dorchester.
Keith Bedford/Globe staff

WHEN I TELL PEOPLE I’m writing about Walsh, the most common question I hear is “What’s he like when he’s off the clock?”

The elementary and middle school students he visits one morning at UP Academy, a charter school in Dorchester, beat me to the punch with a lot of these personal questions.

“What do you do when you’re not being mayor?” one fourth-grader asks.

“Hang out at home, work in the yard,” Walsh replies. “I’m a fanatic about my grass. And I like watching sports.” He was a season-ticket holder with the Bruins at age 21 and then later with the Patriots.

“What do you like to eat? Do you like sushi?”

“Chicken parm is my favorite,” he says. “I’m not a big fan of sushi.”

There are several questions about whether he lives in a mansion and has a private jet.

“God, no!” he replies. His house is a 3,000-square-foot, four-bedroom, three-bath Victorian. He flies coach. “I don’t want people saying, ‘Look at him up there in first class.’ ”

Favorite music?

“U2,” he says. “You know them?” Blank stares. “No? When you get older, you’ll like U2. You know the song ‘Beautiful Day’?” More blank stares.

Favorite store?

“You’re gonna laugh,” he says before confessing that he really likes office supply and stationery stores. One of his first jobs was selling stationery.

One kid shouts out “I like your hair,” to which Walsh replies: “Thank you. I work hard at it.” It’s seldom out of place, though these days he has to remember to spray sunscreen on his scalp because it is starting to thin on top.

When he was in the second grade, Walsh lost all his hair after undergoing chemotherapy for the Burkitt’s lymphoma that very nearly cost him his life. He tells the class he was held back in the fifth grade. He probably should have stayed back earlier, because his illness had forced him to miss so much school. He guesses the nuns at St. Margaret’s School hadn’t wanted to do anything that might have seemed like punishment for being sick. By fifth grade, though, all those absences had caught up with him.

“Are you married?” someone asks.

“No.”

“Do you have any kids?”

“I have no kids.”

After the talk, Walsh tells me, “It’s too complicated to get into everything with Lorrie and Lauren, so I just say no.”

Lorrie is Lorrie Higgins, his girlfriend of a dozen years. They moved in together about two years ago, when Walsh left Savin Hill for Lower Mills — not coincidentally, after Lorrie’s daughter, Lauren, was on her own.

Walsh is devoted to them both, but extremely concerned about protecting their privacy. When I ask him if he considers Lauren his stepdaughter, he says: “I don’t know if I consider her a stepdaughter. I love her. She’s been in my life for a long time now. . . . I feel protective of her. So if somebody messed with Lauren, they’d be messing with my daughter.”

The UP students covered a lot of ground. But to really understand Walsh, I’ve got to pose some deeper questions. And I’ve got to put them to somebody besides Walsh.

Which is why I seek out Danny Ryan.

I catch up with Ryan at McKenna’s, the cafe that basically served as Walsh’s kitchen when he lived around the corner on Tuttle Street. Although I’d never met Walsh before I started reporting this story, I got to know Ryan, a 73-year-old retired court officer, more than a decade ago.

Ryan, who specializes in helping people in recovery make the most of their second chances, got close with Walsh during the first run for state rep in 1997. He became a mentor and eventually one of his closest friends.

This is how he sized up Walsh: “He’s not hard, like a corner kid. He had his tough days, when he drank too much, but I think that was mostly because he was bored with life.”

What impressed him most about Walsh was his sincerity. “He’s never made a mistake of the heart.” He knew the kid had big dreams. “But I never in a million years thought he would become mayor. I still can’t believe it.”

Ryan knew the other big Boston pols, like former Senate president Billy Bulger and former speaker Tom Finneran. When necessary, those guys could be ruthless and hold onto a grudge like a family heirloom. Walsh, he says, is simply incapable of that. “Marty wants to be loved.”

If someone underestimated Bulger or Finneran, these politicians delighted in proving that person wrong. “Those guys all made you wish you had never crossed them,” Ryan says. It sometimes seemed as if they went to bed each night curating their enemy lists. “With Marty, he wants to prove you wrong so he can turn you into a friend.”

Later, when I drive down Tuttle Street, where Walsh lived in a two-family during his years as state rep, Walsh tells me every house in the neighborhood except three featured a Walsh lawn sign during his first run.

“Do you remember which ones didn’t?” I ask.

“You bet I remember!” he replies, then adds, “We’ve mended fences.”

Ryan says Walsh’s desire to be liked can sometimes be a liability. “He has trouble pulling the trigger,” Ryan says. “And he’s is very protective of his staff. If you’re going to knock his staff, you might as well knock his mother.”

Given his age and political chops around Dorchester, Ryan hears a lot of grumbling from older, more conservative Irish guys around the neighborhood who don’t appreciate Walsh’s progressive politics. They dislike all his talk about turning City Hall into a sanctuary for undocumented immigrants and changing bathrooms to gender-neutral and, most of all, his bashing of President Trump, who won their votes.

“But even if they grumble, they’ll still vote for Marty,” Ryan says. “He has the labor background, and they know him and like him.” Besides, a lot of them moved to Braintree long ago.

One group that Ryan says Walsh is particularly determined to win over is “academia.” By that, he means educated voters in places like the Back Bay and Beacon Hill. When Walsh ran against the Harvard-educated John Connolly, Ryan says, “Marty got murdered in those wards.”

Ryan is not particularly impressed by fancy educational pedigrees. (Of his four grown daughters, he says: “They all did OK. No jails, no Yales.”) He senses that some highly educated voters look down on Walsh because of his bumpy college record. But he counsels Walsh not to be too concerned, since it’s foolish to connect academic achievement with success running city government. “You’re telling me Menino and Ray Flynn are gonna take your effin’ SATs for you?” Ryan says. “Give me a break!” 

Boston, MA - 1/29/2017 - Boston Mayor Marty Walsh speaks at a protest against U.S. President Donald Trump's executive orders restricting immigrants from seven Muslim countries at Copley Square in Boston, MA, January 29, 2017. (Keith Bedford/Globe Staff)
At a Copley Square protest in January, Walsh spoke out against President Trump’s executive order restricting immigrants from seven Muslim countries.
Keith Bedford/Globe staff

THE VENEZIA WATERFRONT banquet room is awash in rainbows. Think rainbow sunglasses, rainbow ascots, a white dress shirt painted to resemble the drippy Rainbow Swash on the Dorchester gas tank, visible from the Venezia balcony — all worn by gay senior citizens who have gathered to mark Pride Week.

State Representative Liz Malia takes the microphone. As one of only a handful of out LGBT members of the Legislature, the 67-year-old Jamaica Plain Democrat is a hero to the crowd. A decade ago, Malia played a very public role in the defeat of a proposed constitutional amendment that would have reversed the legalization of gay marriage by Massachusetts’s highest court.

Malia tells the crowd about a role that is far less known: the crucial one Walsh played behind the scenes “bridging the differences.”

“Marty went to a lot of the other reps and convinced them this was the right thing to do,” Malia says. “I’m not sure it would have been possible without Marty Walsh. That’s why he can do just about anything and I’ll support him.”

The crowd erupts in applause, prompting the emcee to grab the mic and say, “That’s called gay love, Mister Mayor.”

People forget how close this state came to scrapping its first-in-the-nation gay marriage decision. Massachusetts may have a national reputation for liberal politics, but its Puritan founding and Roman Catholic dominance die hard. It takes people like Walsh, a guy steeped in conservative Catholic culture, to go around and quietly remind unsure colleagues who share his background that “when your grandkids ask you how you voted on this someday, you’ll want to be on the right side of history.”

Walsh plays that same translator role when it comes to immigration. Unlike most Irish pols of his generation, he is not the grandchild or great-grandchild of immigrants. He is a first-generation American whose parents came from Ireland as adults with eighth-grade educations. Nothing gets his back up quicker than when people start going off on “these immigrants today.”

A few hours after the Pride luncheon, Walsh is the guest speaker at the graduation ceremony of Boston International Newcomers Academy, a public high school expressly for immigrants whose first language is not English. “Don’t let anyone ever tell you you’re lesser,” Walsh implores the students.

He points out that 28 percent of Boston residents were born in another country and 48 percent have at least one parent who was born in another country. He gets so passionate in his celebration of Boston’s diversity that he combines those figures to state that “75 percent of our city is either first-generation or immigrant.” That’s an overstatement, thanks to some double-counting by the mayor. It’s actually been more than a century since Boston was “foreign” at anywhere near that level.

No matter. Walsh stresses that immigrants today are fueling the growth of Boston, just like immigrants did in the past. He’s not going to let anyone demagogue them, certainly not the president of the United States.

Megan Costello, the 30-year-old who ran Walsh’s last campaign and now heads up his Office of Women’s Advancement, tells me about one talk she accompanied him to before a group of more traditional voters. The man introducing the mayor listed such a litany of complaints about Walsh’s progressive politics that she wondered to herself Is this guy going to say anything good about him? But then he ended by saying he trusts Marty.

Walsh did not get defensive or emotional. Instead, he told the group about a pickup truck outside that had two decals on it: one showing union membership and the other Trump support. Calmly but firmly, Walsh built a case for the inherent contradiction of those two decals.

Yes, he told the crowd, Trump may support some positions on social issues that they agree with. But he pointed out that Trump opposes many of the benefits that allowed the union members in the crowd to prosper economically and provide for their families — things like generous health care coverage, pensions, collective bargaining. “What matters more to you?” he asked them. “The social issues or the quality-of-life issues?”

For Democrats to win back the Congress and the White House, they’ll need to get past the anti-Trump screeds and deliver more messages that cut through the clutter like that.

Costello tells me she has no doubt that, at his core, Walsh is “a bleeding-heart liberal.” She’s spent more time with him than I have, but I’m not so sure she’s right.

A bleeding-heart liberal wouldn’t hesitate when asked, for instance, to support changing the name of Faneuil Hall, because its benefactor was a slave trader. But when that question comes up during his monthly appearance on WGBH’s Boston Public Radio, Walsh immediately bats it away. “We are not going to change the name of Faneuil Hall,” the mayor says.

Walsh’s inner compass may tend to point progressive, but it is wrapped in pragmatism. He’s a guy inclined to move left but do it in a way that will create a path for more moderate and conservative people to eventually follow along.

For true bleeding-heart liberals like Costello, that actually makes Walsh more valuable to the cause. If you want to keep crossing rivers, it helps to have a construction worker who knows how to build a bridge.

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