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The story behind Back Bay’s Santa Speedo Run

Runners gathered at the starting line for the 2013 "Santa Speedo Run," the charity race through the streets of the Back Bay neighborhood of Boston, Mass.
Runners gathered at the starting line for the 2013 "Santa Speedo Run," the charity race through the streets of the Back Bay neighborhood of Boston, Mass.REUTERS

It began as a boozy lark born in a Beacon Hill bar at the start of the millennium.

Five guys were sitting at the Sevens, on Charles Street, lamenting their humdrum existence, when one of them threw out the idea of “running down Newbury Street in Santa hats and Speedos while everybody is holiday shopping.” A month later, on a brisk and busy Saturday, the men bolted through the crowded neighborhood in skimpy getups, clutching a boombox blasting the Muppets’ Christmas carols.

Twenty years later, the Santa Speedo Run has become a staple of the holiday season in Boston, raising eyebrows as well as nearly $2 million for a local children’s charity. This Saturday, the bawdy, benevolent tradition will continue when hundreds of scantily clad participants begin their sprint through the Back Bay.

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The event has come a long way since Ryan Birkenhead, Nathan Blew, Seth Frye, Dave Swanson, and Jon Ianelli — a band of bartenders and businessmen — dreamed up the idea back in 2000.

For most of the crew, the run was a short-lived caper. Blew and Swanson retired their Speedos soon after. Birkenhead moved to New York. Frye was crowned champion of an MTV competition to become the boy-toy of Mick Jagger’s ex-wife, Jerry Hall. But Ianelli, a business consultant by trade, pressed on and transformed the escapade into a beloved annual fund-raising event for local children’s charities.

Santa Speedo Run cofounder Jon Ianelli at the Sevens Ale House on Charles Street. This year marks the 20th anniversary of the Boston event.
Santa Speedo Run cofounder Jon Ianelli at the Sevens Ale House on Charles Street. This year marks the 20th anniversary of the Boston event.John Tlumacki/Globe Staff/The Boston Globe

As word and images of the risqué Santas spread, the number of runners multiplied to the point where the city required Ianelli to obtain a permit. After all, " 'You can’t just run in the street with 200 half-naked people,’ ” he remembers a police sergeant sensibly reasoning the morning before the sixth annual run.

In this 2017 file photo, several hundred festive, half-naked runners gathered in Back Bay for the Santa Speedo Run.
In this 2017 file photo, several hundred festive, half-naked runners gathered in Back Bay for the Santa Speedo Run. Dina Rudick/Globe Staff/Boston Globe

Now, the event is capped at 700 runners and has inspired similar Speedo affairs in cities as remote as New Prague, Minn., and far-flung as Budapest.

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In the beginning, the proceeds went to a variety of local children’s charities, but in 2012, a friend put Ianelli in touch with Mike Harney of Play Ball, a nonprofit that funds team sports for underserved middle-schoolers. Since the partnership began, the run has raised $1.75 million for Play Ball and helped revive athletic programs in the cash-strapped Boston public school system. Last year’s run funneled more than $100,000 into the organization.

“[Play Ball] was founded in 2006 on a New Year’s resolution of mine to figure out a way to help inner-city sports programs,” said Harney, the Boston investment banker who founded the organization. “Little did I know it was going to rope me into a lifetime contract of running in a Speedo every year.”

In the first year of the partnership, Harney addressed a gaggle of reporters outside of the Lir pub on Boylston Street in nothing but aviator sunglasses, a Santa hat, and a swimsuit.

“I felt like the guy in ‘Notting Hill’ when he opens the door and all of a sudden there are a hundred camera shots of him in his underwear,” he said.

The ridiculousness of the run tends to overshadow its charitable purpose. Both TMZ and Sports Illustrated have deployed photographers to capture the revelry of the event in years past.

“You finish the day with wind chap in places you never expected to get wind chap. It’s a real issue,” warned Ian Franke, an insurance broker on the board of Play Ball, who strips down each year for the run.

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The event’s website asks participants to abstain from wearing thongs.

Twenty years of this frostbitten humiliation and still the runners turn out. A flock of mothers from Concord. A Mass General neurologist. Thirty-somethings. Sixty-somethings. A marathon runner. Someone with a torn ACL. Another with a ruptured Achilles.

Katie Small (left) and Wendy Krayer will be running Saturday, Dec. 14, in this year's Santa Speedo Run in Back Bay. Small is one of the organizers.
Katie Small (left) and Wendy Krayer will be running Saturday, Dec. 14, in this year's Santa Speedo Run in Back Bay. Small is one of the organizers.John Tlumacki/Globe Staff/The Boston Globe

“All you have to do is run in a bikini to give kids an opportunity that, frankly, our kids in Concord take for granted,” explained Katie Small, who has rallied a team of 14 moms from the tony town to join the festivities. “It’s worth it when you see the joy on these kids’ faces generated by the simple fact that they are playing sports.”

The run — open to anyone 21 and older — starts at 1 p.m on Saturday, Dec. 14. It begins and ends outside Back Bay Social Club at 867 Boylston St. via a 1-mile loop five blocks down Bolyston and five blocks up Newbury.

The sea of scandalous Santas will scamper past the high-end shops of the Prudential Center, the Genius bar lines at the Apple store, and the brunch-goers at Abe & Louie’s and Stephanie’s on Newbury.

“I always say, it’s the longest mile of your life and the Speedo never gets any bigger,” said Harney. “But if this silly, painful thing gets more cleats on the field, sneakers in the gym, and skates to ice, then fine.”

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In this 2017 file photo, runners take part in the Santa Speedo Run in Back Bay.
In this 2017 file photo, runners take part in the Santa Speedo Run in Back Bay. Dina Rudick/Globe Staff/Boston Globe

Hanna can be reached at hanna.krueger@globe.com. Follow her on twitter @hannaskrueger.