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From Fenway Park to the international stage, comedian and his mentor share memories at Ruderman Lecture

Comedian Alex Edelman and Dr. Charles Steinberg were the featured speakers at the Morton E. Ruderman Memorial Lecture at Northeastern

Alex Edelman and Dr. Steinberg sitting on chairs next to each other on a stage in front of a screen that says 'ALEX EDELMAN' on it in pink letters.
Comic Alex Edelman (right) speaks with mentor and baseball executive Dr. Charles Steinberg at the 2025 Ruderman Memorial Lecture. Photo by Alyssa Stone/Northeastern University

A precocious Jewish teen Rollerblades into Fenway Park in Boston …

It’s a bit clunky as a setup, but it’s no joke for Alex Edelman, who visited Northeastern University to recall his journey from Boston Red Sox front office annoyance to comedy star.

“You can either go to a gatekeeper and beg them to let you in, or you can build your own thing and wait for someone to be like, ‘Can we put a gate around this?’” Edelman told Dr. Charles Steinberg, president of the Worcester Red Sox, during a talk Tuesday night. “Sometimes I’ve run right at things, and other times I just focus on my own thing.”

Edelman is a Tony- and Emmy-award-winning standup comedian and writer from Brookline who “oscillates,” as he described it, between solo shows and “comedy as a team sport” by writing on television shows. Now, on what he said is his “third go-around in the cycle,” he writes and appears in the show “The Paper.” 

Steinberg has been working in baseball since he was an intern with his beloved Baltimore Orioles. His roles have also oscillated. He oversaw the Orioles’ oral care as team dentist and also oversaw the team’s public relations department. But Steinberg is perhaps most known to Boston sports fans as the executive vice president of the Boston Red Sox during the 2004, 2007 and 2013 championship seasons.

Edelman and Steinberg were the featured speakers at the Morton E. Ruderman Memorial Lecture at East Village on Northeastern’s Boston campus, an event that mixed inside baseball (quite literally) with comedy and discussion of contemporary Jewish identity.

Throughout his comedy career, Edelman has explored his identity as a modern Orthodox and self-described “troublesome Jew” — the kind of person who would, for instance, write a comedy show about attending a white nationalist meeting in New York. 

“I thought there was something really tangentially political and contemporary about a story about someone who’s white enough to get into a meeting of white nationalists, but not white enough for the people in the room,” Edelman said of the show “Just for Us,” which resulted from the experience. “I think it showed the sort of shades of gray that were very much the language of the Judaism that I was raised with.”

But Edelman didn’t start out writing jokes. 

He started writing after weaseling his way into Fenway Park and telling then-Boston Red Sox President Larry Lucchino to trade an unproductive pitcher. More advice followed, Edelman said, and Lucchino and Steinberg were impressed enough to hire Alex to answer fan mail from other kids. 

“Here’s this little Jewish boy wearing a yarmulke who has an endless supply of questions,” Steinberg recalled. “But we kept giving him more to do, because why not? He wanted to do it.”

Eventually, Edelman became so trusted as a speechwriter that he helped Lucchino and Steinberg script the 2013 ceremony before the first home game following the Boston Marathon bombing. Yes, they anticipated David Ortiz would drop an expletive, Steinberg said.

Edelman also followed Steinberg to positions with the Los Angeles Dodgers and working for baseball Commissioner Bud Selig, all the while honing the stand-up skills that he had developed first at open-mic nights at a pizza place in Cleveland Circle in a neighborhood of Boston. 

Then, while spending a semester abroad in England (Lucchino’s recommendation), Edelman won the Best Newcomer award at the 2014 Edinburgh Festival Fringe for his show “Millenial.”

“It changed my life almost overnight,” Edelman said. “I went from not-a-comedian to a comedian.”

Edelman’s embrace of Judaism has not changed, however, whether he is writing speeches for Red Sox leaders or jokes for the international stage.

“Another Jewish value is that you treat teachers the way you treat your parents,” Edelman said. “In Judaism, teaching is particularly revered, and so I’ve benefited from those teachers, and always tried to show the appropriate level of respect.”

It was clear that Steinberg was one of those teachers.

“You do it in a really notable, generous, meaningful way, and well,” Steinberg said.

Then came the punchline.

“You don’t go to your friends’ funerals, they don’t go to yours,” Edelman said to laughter.