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Jon Lester’s abrupt departure from the Red Sox mound last week left Boston fans reeling. But People’s United Bank faced a billboard-sized headache.

Days before the Red Sox traded the beloved pitcher to the Oakland Athletics, the regional bank featured Lester, their longtime frontman, on a billboard on the Massachusetts Turnpike between Newton and Allston.

But Thursday, when the Red Sox announced that Lester was headed for the Oakland A’s, the oversized advertisement promoting free ATMs from “Fenway to Fort Myers” immediately became outdated. By the weekend, it was a sore reminder of Boston’s loss, as fans posted Twitter, “Just saw the billboard on the way to Boston with Jon Lester ... I cried a little inside” and “#takeitdown.”


But by mid-day Monday, the ad was indeed gone. The bank declined to comment.

People’s United, headquartered in Bridgeport, Conn., signed an endorsement deal with Lester in 2011 as it expanded branches into the Boston area and tried to introduce itself to new customers. The timing of the latest billboard was unfortunate, said Nick Gregorian of Altus Marketing and Management, a sports and entertainment marketing firm that handled Lester’s off-field endorsements.

Lester was the ace of the Red Sox staff. While there were rumors about Lester’s departure from Boston leading up to the trade deadline, “you hold out a glimmer of hope” that it was not true, Gregorian said.

Lester’s endorsement contract with People’s United ended upon his trade, representatives for the pitcher said. John Henry, the principal owner of the Red Sox, owns the Boston Globe.

Tying your regional brand to an athlete always comes with risks, sports marketers and corporate officials said. But many companies are willing to take the hit, since a plug from a well-respected athlete can boost a company’s sales, goodwill and recognition.


“It’s definitely a roll of the dice,” said Joe Bartolotta, a spokesman for Eastern Bank. In 2012, the bank’s partnership with Red Sox first baseman Adrian Gonzalez ended suddenly when he was traded to the L.A. Dodgers in similar fire sale during a disappointing season.

Most endorsement deals allow institutions to break the contract without losing money, if the player gets traded or acts inappropriately, which can include everything from having a drug problem to facing a murder charge.

Some regional companies pay players anywhere from $20,000 to $500,000 year to endorse their products, appear in print and television commercials, show up to corporate events, and mingle with customers at grand openings, said Kim Zayotti, the owner of Norwell-based Blue Sky Sports & Entertainment, who works with several current and retired athletes.

Still, People’s United continues to get its money’s worth from Lester even though he’s now thousands of miles away.

“People are talking about it,” Zayotti said. “Then its clearly working.”

Deirdre Fernandes can be reached at deirdre.fernandes@globe.com. Follow her on Twitter @fernandesglobe.