Framingham’s Skip Flanagan to Face Off Against Red Sox Hall of Famer Jim Lonborg

Flanagan, a local deaf baseball star, managed to coax former Cy Young winner Lonborg out of retirement for a matchup in Thursday's Oldtime Baseball Game.

Jim Lonborg Skip Flanagan

Skip Flanagan with Red Sox Hall of Famer Jim Lonborg. / Photo Provided

Arguably the most intriguing duel this week between a pitcher and batter won’t take place at Fenway Park, but rather at St. Peter’s Field in Cambridge. That’s where Red Sox legend Jim Lonborg will come out of retirement to face former college baseball star, and Framingham’s own, Skip Flanagan.

Like any good matchup, this one has a backstory. Flanagan is deaf and has played baseball throughout his entire life. He recently finished up his senior season at the Rochester Institute of Technology, in which he hit .355 and was named to the All-Liberty League team.

Lonborg, 73, is a former Cy Young Award winner and one of the heroes from the 1967 Impossible Dream team. The ’67 Red Sox captured the American League pennant in improbable fashion after losing the most games in the league just one year earlier. It is the club that is often credited with igniting the baseball obsession that still permeates throughout Boston today.

Flanagan met Lonborg when he was 10 years old at a charity event in one of the Fenway Park suites. The Red Sox great was struck by the precocious pre-teen who was hurling questions at him about facing Mickey Mantle and other greats from the bygone era. They have been friends ever since.

“I blew [Lonborg] up with questions, and that resulted in us sitting down and talking the whole game,” Flanagan said via email. “We became good friends as we began to learn more about each other throughout the night.”

The impetus behind Lonborg’s and Flanagan’s matchup is charity. The two men will play in the 22nd annual Oldtime Baseball Game Thursday night, a yearly fundraiser organized by longtime Boston Herald sports columnist Steve Buckley. This year, the game will raise money toward the Dummy Hoy National Endowed Scholarship, benefitting deaf children from the Boston area who attend the National Technical Institute for the Deaf—Flanagan’s alma mater.

Buckley says the Oldtime Baseball Game’s board of directors like to choose charities that arise organically from the game. Last year, for example, all of the contest’s proceeds went to ALS research. Former Boston College baseball captain Pete Frates, a veteran of the game and face of the viral Ice Bucket Challenge movement, made a symbolic appearance.

Flanagan, 22, has played in the game three times before, but this year’s cause holds a lot of importance to him for obvious reasons.

“Success in sports is largely based on one’s talent and work ethic,” Flanagan said. “Dummy Hoy and Curtis Pride worked their tails off to become successful Major Leaguers. They had to overcome tons of adversity to make it to the bigs, and they were blessed with great talent and work ethic to begin with.

“I am very proud of the Deaf Community, and I want to do as much as I can to help the community grow and improve every day.”

Buckley recruits some of the most talented college baseball players in the region to play in the game at the end of each summer. Over the years, a bond between Oldtime Game alumni has formed.

“We look for guys who recognize baseball can be played in a philanthropic manner,” Buckley said. “We have a lot of legacies. A guy will play three or four years in our game and recommend someone else. Three of our coaches are guys who played in the game.”

Flanagan hopes Thursday night’s game is one of many stops on the way to the big leagues. He signed on to play in the newly formed North Country Baseball League this summer, and says he wants to continue to play professionally. Flanagan led RIT to its second-best record in more than 60 years of the program’s history and to the team’s first-ever Liberty League championship.

But first, there is the matchup with Lonborg. It has been years in the making, and shows the bond that sports can form between two of the unlikeliest bedfellows.