Chris Dempsey Picks His Best Bostonians of All Time

The No Boston Olympics co-chair's picks for Best Bostonians draw upon famous names from the past and present.

We’re asking prominent locals who they think are the Best Bostonians of all time. Below, Joe Bagley shares his picks. Play along by voting in our online game.

Chris Dempsey

Chris Dempsey. / Photo by Andy Laub

Paul Revere

“The North End native is known for his heroic midnight ride, but Revere was also a political agitator and an accomplished silversmith and entrepreneur. He was a lead organizer of the Boston Tea Party, and his engraving of the Boston Massacre helped publicize the revolution that was brewing in the streets and meeting houses of 1770s Boston.”

Frederick Law Olmsted

“America’s preeminent landscape architect, Olmsted designed New York’s Central Park and Prospect Park, and, of course, Boston’s Emerald Necklace. Olmsted re-imagined how cities could incorporate nature, and created egalitarian urban parks that he saw as vital contributions to democracy. He lived on a quiet street tucked away in Brookline off Route 9.”

Isabella Stewart Gardner

“The independent and unconventional Gardner brought some of the world’s best art and artists to Boston, and then generously left her collection and home as a lasting legacy for Boston residents. She was also one of the original Red Sox fans—she caused a scene when she wore a Sox headband to the stodgy Symphony.”

W.E.B. Du Bois

“Du Bois was a Massachusetts native and lived for a time on Flagg Street in Cambridgeport. Born just three years after the Civil War, he lived until just a year before President Johnson signed the Civil Rights Act. In between he cofounded the NAACP, authored
some of the most important books on race in our nation’s history, and was a strident and effective voice for a more perfect and equal nation.”

Michael Dukakis

“One of my earliest memories is sitting on my dad’s shoulders on Perry Street in Brookline outside of Governor Dukakis’s home on the night of the ’88 presidential election. Dukakis remains the Commonwealth’s longest-serving governor. With help from his Secretary of Transportation, Fred Salvucci, Dukakis expanded the MBTA and pushed through the Central Artery project. Almost 30 years after running for president, he is still contributing to our civic debate, still taking time to pick up trash on his walk to work, and still riding the T.”


Whom would you choose? Help us pick the Best Bostonians of all time.