The Subtle Art of Being Ernie Boch Jr.

Boch, before his extreme makeover, outside his used car dealership in 2003. / Photograph by Tom Herde/The Boston Globe/Getty Images

Boch Sr. died in 2003. Along with his business empire, and his dying-breed Boston patois, Boch inherited his father’s knack for publicity. Even as he began to sell off retail dealerships, he arranged for them to retain the Boch name. (He kept two luxury car dealerships and built up the Subaru of New England cash cow, which remains his primary business concern.) Instead of appearing on camera to sell cars, though, Boch began asserting himself as a media personality in his own right. He toured the local shock-jock circuit, joining WAAF’s Greg Hill and WRKO’s Howie Carr with regularity. “Ernie wasn’t going to be talking about automobiles, but projecting a lifestyle,” says his friend and ad guru Bruce Mittman, who used to run WAAF.

Boch stopped wearing suits, literally grew his hair out, and started drifting back to music. In 2004, he formed a band called Ernie and the Automatics, paying a couple ex-members of the band Boston to tour with him. The group’s lone album, Low Expectations, experienced some success on the Billboard charts, and the group opened for a handful of major acts. Still, the troupe wasn’t cutting-edge. At a charity roast of Boch several years ago, emcee Joel McHale, formerly of The Soup, joked that “Ernie and the Automatics” sounded like the name of the Sesame Street band.

From Boch’s perspective, though, it was on-brand. Playing guitar in a middle-aged blues-rock outfit wasn’t so different from appearing at charity events with Lenny Clarke, or doing bit parts on Denis Leary’s Rescue Me. Boch projected a macho populism that felt blue collar, but was really aimed at restive suburban consumers, like himself.

Over time, Boch the brand and Boch the guy became inseparable. Just as Boch père was blackballed on Martha’s Vineyard, Boch’s conspicuous style denied him entrée to the Boston power elite. It also gave him a common touch. He is, as his friend Michele McPhee, the crime reporter and Boston contributor, puts it, “a white-trash rich guy.” During a Patriots game in 2004, he hosted a particularly debauched bacchanal in his luxury suite at Gillette Stadium. “It got kind of crazy,” he recalls. “Girls were drinking, people were passed out.” Security eventually quashed the ruckus and threw Ernie out of the building. Soon after, he was banned from his box entirely. “So [the Krafts] sent me a letter and said, ‘Hey, listen, you’re a deplorable. We don’t want you in the stadium, we’re terminating your contract,’” Boch tells me. The two sides eventually reached a truce, but Boch was still steaming at the Patriots’ owners—not so much for punishing him, but for sending a lawyer to do it on their behalf. Boch says he kept the suite but hasn’t been back to a football game there since. The Patriots did not respond to a request for comment.

In 2010, Boch and his wife, Kristen, a fellow Norwood native, split up after more than a decade of marriage. (They have two children together, both teenagers.) Since then, the experience of middle-aged singledom has left Boch a little cold. “After 11 years,” he reminisces, reclining in the back of the stretch, “I tried to bang my way to happiness for about a year. And you know, it was fun.” Peggy Rose stares at him and asks, “Is this on the record?” Boch replies, “Yes, this can be on the record.” He resumes: “I tried to bang my way to happiness. Which, if anyone tries, never works. But everybody tries.”

In due time, he rebounded with another “Inside Track” favorite, former Ben Affleck and Kevin Youkilis paramour Enza Sambataro. “He thought she was so hot,” Raposa says. “He’d ask me, ‘Isn’t she hot? Isn’t she hot? Isn’t she hot?’ He likes hot girls.” But that romance sputtered, too. “We went out for a year and had a child together, who I love dearly,” Boch says. “Then she broke up with me. I stayed too long at the party. And I realized: You cannot force anyone to love you.” Four weeks later, Boch informs me that he and Sambataro have gotten back together.

It’s never made clear to me if our trip to the Wang Theatre at the Boch Center has been scheduled for my benefit or if Boch is just curious to see it empty, in the middle of the day. We arrive at around 3 p.m. and are greeted by communications and marketing director Michelle Chapman. The news of the hour is that for the first time in 30 years, the Wang has renovated its plush red seats, the theater’s inaugural capital project of the Boch era. Peggy and I pet the handiwork admiringly. Boch asks Michelle if the theater maintains an active Snapchat account, receives a satisfactory answer, and then turns his attention to the baroque space itself. “Isn’t this incredible? It almost looks fake,” Boch says, surveying the 3,500-seat theater in all its refurbished glory. “You should have seen this place in the ’70s. The first place I ever saw anyone smoking pot was in the basement here. I never even knew you could do that.”

Boch Center CEO Josiah Spaulding II hails from Grade A Brahmin stock. His mother, Helen Bowdoin Spaulding, a descendant of Bowdoin College’s namesake, helped create the New England Aquarium. His father, Josiah Spaulding, was a major player in Republican state politics. So when Citi decided not to renew its sponsorship with the organization that runs the Wang and Shubert theaters in 2016, the libertine car dealer wasn’t an obvious choice to fill the gap. Boch himself was shocked when Spaulding made the ask over lunch. “I told him he was fuckin’ crazy,” he says. “That’s out of my league! That’s like Gillette doing a stadium!” But Spaulding made a compelling pitch, and by their second bottle of wine, Ernie was more or less convinced. For his part, Spaulding says he was attracted by Boch’s relationship to the venue—he’d gone to shows there as teenager, and played there with the Automatics as an adult—but also by his surprisingly puppyish enthusiasm for music education. “He lives every day the principle that arts keep us a civilized society,” Spaulding tells me.

In 2005, Boch joined Berklee’s board of trustees, where he has led several major fundraising campaigns. A year later, he started Music Drives Us, a charity that has placed instruments in and paid for music programs in roughly 200 underfunded public schools in New England, including more than a dozen in Boston. Clearly this is his baby, and one of the few subjects that snap him out of his stream-of-consciousness musings. “I’ve funded Boston public schools that had music programs without instruments, music programs literally in basements next to the water heater,” he says. “It should be standard, standard stuff in schools, just like math.”

In Boston, the problem goes beyond public-school funding. By late 2016, the city’s entire performing arts scene appeared on the brink of collapse. Not long before Citi pulled out, Boston Lyric Opera announced it was leaving the Shubert to find a less cramped, creaky venue. Earlier that year, BU announced plans to sell the Huntington Theatre, while Opera Boston had shuttered completely four years earlier. (Emerson College even considered turning the Colonial Theatre into a cafeteria.) Precipitating the tumult was a financial crunch whose severity had only begun to come to light. Earlier that year, the Boston Foundation had released an alarming report about the state of arts funding in the city. It found that while per-capita giving keeps pace with other major cities, the parity is misleading. Just three organizations, WGBH, the Museum of Fine Arts, and the Boston Symphony Orchestra, account for 40 percent of the arts sector’s market share. Take them away, and Boston looks more like Minneapolis than San Francisco.

Compounding the problem is weak corporate giving, and a stingy public sector. The city of Boston, compared to the nine other cities the report studied, gives next to nothing to the arts. A domino effect of unintended consequences is partly to blame. Because of Massachusetts’ complex home-rule provision, Boston cannot raise taxes without state approval. Instead, it relies almost entirely on local property taxes for its revenues. But because Boston is full of nonprofit universities and hospitals, more than half the land in the city is non-taxable, leaving very little for the arts. Meanwhile, despite his self-styled reputation as the “Arts Mayor,” Marty Walsh’s ambitions for the cultural sector have been ill defined and slow to materialize.

Boch doesn’t have much to say about political or structural quagmires. At one point, Chapman has to remind him that he is in fact a member of his own theater’s board. His loose take on the whole matter, though, is that the Theater District’s stodgy grandees might follow his lead and open their wallets a little wider. “The old Yankee mentality is disgusting in a way,” he says, standing on the stage of the empty Wang Theatre. “It’s frugal. I was at a fundraiser on the Vineyard. Forty dollars a ticket. I said to the lady, ‘This is cool, when do you start raising money?’ There were rock stars there! She said, ‘Oh we raised the money—you bought the ticket.’” Boch grimaces. “I grab the microphone and I go, ‘I’m going to give $100,000 right now. Who’s gonna match me?’ Raised $600,000. Just by asking.” (Spaulding won’t reveal what Boch is paying to underwrite the Boch Center, but claims it’s more than the roughly $1.1 million to $1.6 million Citi was shelling out each year, and for longer than the 10 years Citi stuck around.)

Boch’s point is well taken, but his flashy, improvised brand of generosity is as likely to irk the city’s traditional donor base as it is to please its beneficiaries. “He’ll bounce around from subject to subject with no warning,” says his friend Dave Andelman, of The Phantom Gourmet, “based on what he thinks is interesting.” The same principle applies to Boch’s charitable giving. In September, Curt Schilling mounted guerilla rescue efforts to provide relief to victims of Hurricanes Harvey, Irma, and Maria. The effort naturally raised eyebrows among legitimate aid groups, but Boch, who shares the former Red Sox pitcher’s right-wing politics, gave him $175,000 without hesitation. In 2014, Boch was approached by National Geographic to star in the pilot episode of a reality show. In it, he would travel to a remote locale, pretend he was filming a documentary about “world music,” then surprise the natives with his generosity. It was called Undercover Angel and it sounded to him like a swell idea. He agreed to do it without knowing where he was even being sent. In late 2015, armed with a duffel bag and a guitar, looking like a very lost troubadour, he set off for a village in remote Uganda, 200 miles west of the capital.

Boch did not find his experience to be a romantic one. “I’m glad I went, but had I known how I would have lived,” he says, “I wouldn’t have gone. Wouldn’t have fuckin’ gone. Don’t give a shit what they would have said. Don’t care what it was, national TV, whatever.” Inconveniences, he says, included: “Rats, and the spiders, and the heat! And everybody had bad breath and body odor and it was fucking disgusting—and everything is dirt! Nothing is clean!” This is harsh stuff, but after experiencing third-world poverty for a couple of weeks, he did ultimately build the town a school and several latrines, and installed water wells throughout the region. Put another way: A destitute slice of East Africa benefited from Boch’s munificence, precisely because he had given zero thought to the implications of going there in the first place.

Ernie Boch Jr. isn’t totally oblivious to the concept of bad optics. Peggy Rose, eager to keep me entertained, insists that Boch show me his private jet, a svelte white Cessna Citation Sovereign sitting in a hangar near the Automile. Boch balks repeatedly, but Peggy is persistent, so after the Wang visit, Ned steers us back to Norwood to scope it out. My experience with private jets was previously limited to photographs of Trump’s gilded 757 and Air Force One. This nine-seater is decidedly smaller; when Boch off-handedly reminisces about “naked women” who’ve spent time in the plane, I have trouble figuring the geometry of the orgies.

There is a leather-bound guest book on the jet. To an extent, it reflects Boch’s merry Rolodex of B-list celebrities. In 2007, Donnie Wahlberg signed, “Save for the insane turbulence, it was cool. You almost wiped out 3/5 of New Kids before we could do our reunion.” Two entries in particular are more surprising—both signed, in immaculate handwriting, by Mitt Romney when he was first running for president. “Commander General Boch, friend Ernie,” read one, with genial familiarity. “Thanks so much for ferrying me to and from Hillsdale College in Michigan to my commencement speech. Your generosity has once again made my effort possible. —Mitt.”

I found it impossible to read this and not wonder how a friend of the ever-decent Romney could wind up a Donald Trump fanatic. In the summer of 2015, Boch got in touch with Trump’s then–campaign manager, Corey Lewandowski, to ask what the protocol was for throwing a fundraiser. Lewandowski told him he didn’t know, since no one had thrown one yet. Boch was summoned to Trump Tower for a planning meeting that lasted about eight minutes. “I went up to his office. And he wasn’t president. But you could feel, like if I was going to go in there and negotiate with him about something, he would have killed me,” Boch says. “I met [Bill] Clinton, met both Bushes, super-powerful business guys, and they all have this aura around them. They have this fucking thing, this charismatic quality that knocks you over. Every president had it. Trump had it.”

The Donald gave his blessing, and Boch threw his bash in August 2015. One hundred a head for mountains of food and an open bar. Everyone Boch knew showed up. CNN carried the event live, and soon Boch was being hustled onto cable news shows to talk politics. “When it got crazy, every time something happened, they’d bring me on to defend [Trump],” Boch says. “And then he’d do shit, and I’d be like, ‘How the fuck am I going to defend that?’” Boch became a brief national sensation, and minor regional embarrassment, when he appeared on one segment in a dandyish scarf and declared that choosing Trump was like picking up a girl at a bar at closing time: You had to go home with somebody. “I told Peggy, they’re gonna wake up one day and find out I don’t know what the fuck I’m talking about and they’re gonna stop calling me to come back. And sure as shit, they did.”

In August 2015, Boch held a fundraiser at his mansion for Republican presidential hopeful Donald Trump. / Photograph by John Tlumacki/The Boston Globe/Getty Images

Why, exactly, does Boch support Trump? I’m having lunch with Boch when I mention that the president plans to deport the so-called Dreamers. He is dismayed. “See, that’s the shit you say to him, ‘What the fuck are you doing? There’s so much shit you could be doing besides that.’” The only policy I hear Boch talk about—cutting government spending—has little to do with Trumpism. Rather, like so many of the president’s unlikely supporters, it seems Boch saw something of himself in the mogul. “I had been a fan since the ’80s,” he says. “If you were a business guy, Trump, he had character. Super successful, doing crazy things. He was a showman, a promoter. I mean, you know, I dug it.”

Like Trump, Boch capitalized on the success of his overbearing father to create a theatrical persona for himself. There is also an ad hoc, Trump Tower feel to Subaru of New England. At a marketing meeting I attend, discussion of company business is almost completely intermingled with planning for his charity, Music Drives Us, which is technically part of the Boch Family Foundation. Boch’s ever-patient secretary, Joyce, is on call at all hours; on the way to dinner one night he rings her from his Bentley convertible to ask her to look into the car’s spotty satellite radio feed. Tellingly, Boch commissioned a local artist named Giovanni Decunto to paint portraits of his father, grandfather, and Trump—all three of which hang in the lobby outside his office.