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This colorful Boston developer is enjoying his last [bleeping] hurrah

Dick Friedman eyed the crane at work on One Dalton, the 742-foot tower he has developed in the Back Bay.David L. Ryan/Globe Staff

Note to readers: Throughout this profile of Boston developer and hockey fan Dick Friedman, the profanity known as the f-word has been replaced with “Zamboni.”

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We are knee-bucklingly high up in an unfinished skyscraper. The walls are open, and the winter wind cuts like a razor. Richard Friedman is stalking around with impatient energy, wearing a hard hat he admits doesn’t get much use.

“I’m not a young man,” says Friedman, 77, a real estate specialist best known locally for developing the Charles Hotel in Harvard Square and the Liberty Hotel in Boston. “I’ll never get another chance to do something that changes the city like this.”


Under construction since early 2015, the One Dalton tower — Dick Friedman’s signature on the Boston skyline — is now peeking above neighboring buildings in the Back Bay. It marks a return to the Boston development limelight for an outsized personality who is comfortable in the bright lights, tapping elbows with stars, but whose name might not ring a bell for many Bostonians today.

When it opens early next year, the roughly $850 million One Dalton project may be Boston’s most exclusive address, with a Four Seasons hotel on the bottom and pricey condos above.

At its planned height of 742 feet, One Dalton will stand as Boston’s highest residential tower and third-tallest building, within a whisker — 48 feet — of nearby 200 Clarendon, the former John Hancock Tower. So close, in fact, that it raises the question:

Why build the third tallest building?

Friedman sputters some nonsense about zoning or such before he admits, yeah, it could have, should have been a tad taller.

“I Zambonied up,” he says.

Friedman is a fun interview, an energetic storyteller who laughs easily, switches topics on a dime, and speaks with a gravelly voice. Though he never cultivated the public persona of more high-profile developers, Friedman appears to know and have befriended just about every boldfaced name you can think of. Charles Hotel staff Google their guests and send Friedman a list every day of interesting people they think he might want to know about, he says.


David Mamet applauded as Hillary Clinton was hugged by Friedman.Bill Greene/Globe Staff/File 1999

After opening the Charles in 1985, Friedman was widely known in the 1990s for hosting Bill and Hillary Clinton at his Martha’s Vineyard property, spurring breathless news stories about the propriety of the vacationing first family getting free rent from a businessman. (Such stories seem adorably old-fashioned now, in the Trump era.)

Friedman has since popped up occasionally in the local headlines, most notably a decade ago when he opened the high-end Liberty Hotel in the shell of the old Charles Street Jail.

“How do you turn something from terror to joy?” Friedman says, referring to the jail’s reputation as a hellhole. “That’s something I tried very hard to do. I love seeing people having fun in the hotel and restaurants. I love people having sex in the hotels. I love people having honeymoons and weddings.”

He is enormously proud of the Liberty and insists we tour it at the end of a daylong interview. He is, naturally, a rock star there: The valet calls him “Dad-dee!” and demands a hug.

If everyone has a superpower, one thing they do better, or think they do better, than anybody, Dick Friedman’s is making friends. He is drawn to the accomplished and the famous, whose names he sprinkles through conversations like dry seasoning. Carly Simon. Gregory Peck. John Kerry. Skip Gates. Friedman cried the time he was hugged by the Dalai Lama. Former senator Chris Dodd, a longtime friend, says he checks in with Friedman about once a week.


Former US senator Chris Dodd (right), a longtime friend, says he checks in with Friedman about once a week. Above: Friedman and Dodd at a 2003 event..Bill Brett/Globe photo/file

“There’s an energy that comes out of successful people in any field,” Friedman says.

His pals populate the upper reaches of politics, entertainment, and business.

“There’s nobody like him,” says David Mamet, 70, the playwright and Hollywood moviemaker, who has been Friedman’s friend for decades. “He is literally a nice guy. Of course he swears all the time. Also, I think he’d die if he ever read a book.”

Longtime Friedman pal Millard “Mickey” Drexler, chairman of retailer J. Crew, says Friedman works hard at friendship. He remembers Friedman once flew cross-country after surgery, with an IV line attached to his arm, so he would not miss a friend’s wedding.

“He has a very high threshold,” Drexler says, “for discomfort and pain.”

That’s helpful — since Friedman’s buddies skewer him mercilessly.

“He’s been a great disappointment to me and [Newbury Street clothier] Alan Bilzerian,” Mamet deadpans. “Alan’s been trying to get Dickie to stop dressing like he just got out of Kmart.”

Sad but true, says Bilzerian, 74, Friedman’s friend for 40 years. “I’ve asked him — please, let me come over and take your closet apart.”

Dick Friedman can take a joke. He repeats the good ones.


“Bill Clinton says I have a kid every 27 years,” says the twice-married Friedman, whose sons are 46 and 18. He says his wife, Nancy, talked him out of getting a trim before he met with a Globe photographer. “She said, ‘When you have a short haircut you look like Mike Pence.’ Fine, I won’t get a haircut.”

Friedman is also creative and relentless, his friends say. About a month ago, Friedman and Bilzerian were driving around Los Angeles, looking at hotels Friedman might want to buy.

“I said, ‘Dickie, how old are you? How much longer are you going to do this?’ ” Bilzerian recalls. “He was adamant, ‘Don’t even ask me about retiring.’ ”

“He’s got a lot of natural drive,” Bilzerian says. “If you were going to loan him $200 million, you’d look at him and say, ‘I can trust him. He’s going to bust his butt to pay me back.’ ”

Boston Bruins president Cam Neely befriended Friedman about 20 years ago, after they met through a mutual friend. Neely says Friedman helped him after his playing days ended in the 1990s. “I turned pro at 18, no college education,” Neely says. “Being in my 30s and retiring from a sport that was my whole career — it was daunting.”

He engaged Friedman in long, free-flowing conversations about business. “I went into it like a sponge,” he says. “He was also pressing me about what I might like to do. He has a really endearing way and all kinds of energy.”


They still golf together. Friedman on the links, Neely says, is Friedman squared.

“Dick is so competitive, it’s so freaking funny. He starts out telling himself this is a social thing and then hits a couple bad shots and it’s, ‘Zamboni this! I Zamboniing suck!’ ”

When finished, the One Dalton tower developed by Dick Friedman will be Boston’s third-tallest building.David L. Ryan/Globe Staff

The One Dalton tower was designed by 200 Clarendon architect Henry Cobb, making a return to the Boston skyline’s upper reaches, in collaboration with Cambridge Seven Associates. No expense was spared for quality, Friedman says.

The easy criticism of the building is that it is light-years beyond the financial reach of most Bostonians.

“Do we really need another top-end, gazillionaire-owned condo tower?” says Richard Giordano, director of policy and community planning for Fenway Community Development Corporation.

It could seem incongruous that a property so tuned to the 1 percent is being developed by someone who did not come from wealth and is extremely candid about his regular-guy flaws.

Says Friedman: “I’m an extraordinarily bad manager”; “I have a fair amount of fear of failure”; “I’m a bit rude”; “I say Zamboni too much.” He begins to describe his short attention span but doesn’t finish the story before he veers into another.

Friedman works 80 hours a week, traveling often. He’s building a hotel in Iceland and another in New Orleans. There’s some truth in Mamet’s joke that Friedman doesn’t read many books. He does devour newspapers and periodicals.

“I read architectural magazines like somebody would read Playboy,” Friedman said.

On the tour of One Dalton with Darren Messina, Friedman’s executive vice president, Friedman admits his team does not enjoy his visits to the site. He tends to fiddle.

“He thinks because something isn’t built yet it can be changed,” Messina says. “Like all these decisions were not made two years ago.”

Friedman was born in Cambridge and says he grew up middle class in Brookline. His father was “the smallest real estate guy you could possibly be,” Friedman says. “He was not entrepreneurial; just very afraid of losing whatever he had.”

Friedman became the opposite.

“I take risk all the time.” A former Harvard ski coach, Friedman once broke his neck on the slopes, yet still likes to ski fast. “I’m very hard-driving. But measured. I don’t take legal risks. I try very hard not to do business with people I don’t like. I think it mitigates risk.”

Friedman’s left-leaning politics may have come from his mother, Helen, whom he recalled as a “very liberal social worker,” a Bernie Sanders voter before there was such a thing. Thanksgiving dinner usually included a couple of homeless people at the table, he says.

He went to Dartmouth for college, where he was on the ski team and studied philosophy.

He has worked a lot of odd jobs. Door-to-door knife salesman. Dishwasher. He delivered flowers, liquor, and newspapers. He sorted mail, caddied, worked in demolition, taught waterskiing.

The commercial real estate industry launched him. He handled leasing for retailers such as Radio Shack and Ann Taylor, then became a developer, doing projects with the Pritzkers, the family behind the Hyatt chain. He gives tremendous credit to the team at his firm, Carpenter & Company.

Friedman developed Liberty Hotel in the West End.Aram Boghosian for The Boston Globe/File

In the small world of Boston developers, Friedman is well liked.

“Dick is known for quality work,” said developer Ron Druker. “He does a few things at a time and does them well.”

Developer Don Chiofaro said Friedman is smart and a straight talker. “Not always true in this business.”

Along the way Friedman became extremely wealthy, and a major political donor to Democratic candidates.

Friedman insists money did not change him, that he’s still the same guy. Still frugal. Has his suits made in China, not London. Still working hard from an unassuming office at the Charles.

“I don’t like people who talk about money all the time,” he says. “I like to do well, but I don’t do a project just to make money. It’s to do something that’s fun. I don’t find it to be work.”

His is not a rags-to-riches story. It’s a well-educated-middle-class-kid-to-riches story. But he has done some cliché rich-guy things, such as buying a black Porsche and fighting with Vineyard neighbors in court over beach rights. He will be moving from Cambridge to One Dalton. And yes, he has a plane.

At the mention of jets, Friedman tries to tell a story — off-the-record — about a time he was on the Vineyard with Mamet and the late Shel Silverstein, the Playboy cartoonist and author who wrote “The Giving Tree.”

But Mamet had already shared the anecdote, which goes like this: The three were out walking. Friedman, then unmarried, was accompanied by an attractive, younger woman, prompting Silverstein to note, “There goes a guy with a plane.”

Mamet says, “I think I put that line in a movie.”

Friedman chuckles over the story, but dismisses it also. It all happened long ago, and he is not a nostalgic guy. He starts to mimic tedious nostalgia, “Remember the time . . .” Then cuts himself off. “Zaaaaaamboni you! I like new friends and I like people who are active in doing things.

“If you’re looking backwards, that’s a strange way to drive, right?”

He seems absolutely delighted to have apparently coined a phrase.

“I just invented that!”

“There’s an energy that comes out of successful people in any field,” Friedman says.David L. Ryan/Globe Staff

Mark Arsenault can be reached at mark.arsenault@globe.com. Follow him on Twitter @bostonglobemark.