CEO Files

Carpenter & Co.’s Richard Friedman

A real estate developer talks about his arresting new project
Interview by Sharon McDonnell - December 1, 2008
 Carpenter & Co.’s Richard Friedman
“The Liberty Hotel is about transformation, and how to make a jail into a joyous place.”

Real estate developer Richard Friedman has been winning plaudits for his unusual latest project: the transformation of the historic Charles Street Jail in Boston’s Beacon Hill district into the luxurious, award-winning Liberty Hotel.

Built in 1851, the jail housed the alleged Boston Strangler, a mayor of Boston and the controversial anarchists Sacco and Vanzetti. It was closed by federal order after prisoners rioted in 1973. Friedman’s company spent $150 million to acquire and renovate it, adding a bar in the former “drunk tank” and a restaurant named Clink, while preserving the 90-foot atrium where prisoners exercised, as well as iron bars on windows and some cellblocks.

The Liberty caps more than 30 years in real estate for Friedman, who also developed the St. Regis hotel in San Francisco, the Charles Hotel in Cambridge, Mass., and three Hyatt Regency hotels in Texas and Cambridge, as well as shopping centers from Connecticut to suburban Chicago.

Friedman is also involved in politics. Appointed by President Clinton as chairman of the National Capital Planning Commission in 2000, Friedman said he resisted efforts after 9/11 to turn the capital into an “armed camp.” He founded the Interagency Task Force, which works with the U.S. Secret Service and U.S. Department of Homeland Security to improve security in Washington, and was finance co-chairman of Senator Chris Dodd’s presidential campaign in 2007.


How would you describe your management style?

I’m a pain in the neck. I try to find out what’s wrong. I have an overly relentless drive for perfection. It’s like the joke about the waiter at a Jewish resort in the Catskills who comes to a table to ask, “Is anything OK?”

What’s your business philosophy?

You have to look long term, you can’t look at quarterly results.

What are your best and worst traits?


I’m a good guy and extremely loyal. I have people who have worked for me 10, 20, 30 years. I don’t give up, and I love the expression, “the harder you work, the luckier you get.” But I can’t tell the distinction between work and play, and I’m impatient and rough.

What attracted you to the hotel business?

Hotels are part real estate, part theater, part promotion. I like the vitality and sensuality of a hotel–designing it and merchandising it brings together a lot of skills and things that interest me.

Why build a hotel in a former jail in Brookline, Mass.?

It’s the most fabulous building in a fantastic location in Boston on the Charles River. It was a magnificent opportunity to restore a federal, state and city landmark, and I was crazy enough to take it on. I don’t know what they were thinking in 1851 to build it as a jail.

Was converting a jail and thrice-landmarked building daunting?

In hindsight, it should have daunted me a lot more than it did. I’m very tenacious and love to be creative, but it was very hard to finance and get people to believe in it.


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