Auctioneer Dan Flynn a fixture on charity event circuit

Kayana Szymczak for The Boston Globe
Dan Flynn ran a charity auction at “Tackling Duchenne,” a benefit for JB’s Keys to DMD, at the Boston Harbor Hotel last month.

By day, Daniel J. Flynn is a strait-laced real estate broker and auctioneer.

But on nights and weekends Flynn hits the local charity auction circuit, where he could easily be mistaken for a stand-up comedian. A merry banter and an irreverent sense of humor — paired with his ability to squeeze money out of the crowds in creative ways — make him a go-to guy on the fund-raising gala circuit.

“One week, I saw [Red Sox CEO] Larry and Stacey Lucchino on a Thursday and Saturday night,” recalled Flynn, 52, of Milton, “and when I walked into the ballroom Saturday they said, ‘Dan, should we just adopt you?’ ”


Flynn estimates that he runs 45 charity auctions a year, and up to five a week in spring and fall, the busy seasons for galas. His fee is typically 10 percent of total auction items sold, and the work has made him a student of facial expressions and body language.

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“There’s nothing greater than when a husband is bidding and his wife digs her nails into his thigh,” Flynn jokes. “I’ll say, ‘Sir, that means bid higher!’ I can only imagine how many guys have had to go home in a cab because they bid on a golf trip they weren’t supposed to.”

Besides auctioning donated items like trips and tickets to sporting events, Flynn is always on the hunt for additional money-raising opportunities, like spontaneously auctioning off meals with politicians in the room.

This winter, at a fund-raiser for Newton Country Day School, he surprised the headmistress, Sister Barbara Rogers, by offering her as an auction item: He told the crowd that after the next snowstorm she would plow the driveway of the winning bidder.

The offer quickly got snapped up — for $2,000.


Before the event, Flynn said, Rogers had requested that he keep his humor “appropriate” (“So I could not do a single nun joke, and I have a repertoire of nun jokes!”) and afterward he asked her how he’d done.

“She told me I was very appropriate,” he said.

For the record, Flynn said he doesn’t actually expect Rogers to deliver on the plowing, “but I did say it’s good until next season when we get another blizzard,” he wisecracked.

Sacha Pfeiffer

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