Roger Bennett of ‘Men in Blazers’ is a ‘Chicagoan trapped in an Englishman’s body’

According to family legend, Roger Bennett’s great-grandfather fled Eastern Europe in the 1910s intending to move to Chicago. He was a kosher butcher, so living in the city Carl Sandburg dubbed “Hog butcher for the world” made sense. But the journey to Chicago via New York didn’t go as planned.

“The myth of our family is that the boat docked in Liverpool [England] to refuel,” Bennett said, “and he saw the one tall building on the Liverpool skyline and, like other low-IQ individuals on the boat, was like, ‘Hey, we’re in New York; everybody off.’ ’’

Thus began the Bennett family’s existence in Liverpool, and with it, a multigenerational longing to be elsewhere.

“I always told myself in Liverpool I was a Chicagoan trapped in an Englishman’s body,” Bennett said.

Bennett is the co-host of “Men in Blazers,” which began in 2010 as a podcast about the Premier League and turned into an eclectic, energetic TV show in 2014 on NBCSN. Bennett and co-host Michael Davies tackle much more than soccer, bringing on stars who range from media to movies to sports.

But when there were no sports last year during the lockdowns of the pandemic, Bennett turned to a different medium. He wrote his fifth book, “(Re)born in the USA: An Englishman’s Love Letter to His Chosen Home,” in which he explains the influence Chicago and American culture played in his life.

Writing proved cathartic for Bennett, whose memories of setting and feeling are remarkably vivid, as though he just relived the events. That’s because in his mind, he did.

“In the chaos of the present, I did teleport myself back to a happier time, and so many of those happier times of my youth took place in Chicago or in the Chicago of my imagination,” Bennett said. “Liverpool had high unemployment, high crime, a heroin epidemic. It was real hopelessness.

“And America, even before I’d set foot there, was just a place in my imagination where I retreated, feasting on American culture, the movies, the books, the music, the Chicago Bears’ Super Bowl-winning run, and it gave me such life, such joy, such meaning, ultimately such hope.”

Bennett, 51, is now an American citizen living in New York. But a trip to Chicago in the summer of 1986 to visit a friend in the north suburbs became a life-altering experience.

“I felt like I walked through the looking glass and arrived in my own John Hughes movie,” he said. “I had never been there, but it was all so bloody familiar because I had seen it all on the screen. It was all just as I imagined.”

When NFL highlights were beamed to British TV in 1982, Bennett adopted the Bears because of his great-grandfather. During his visit to Chicago, the Bears, ironically, played an exhibition game in London. When they returned, Bennett and friends staked them out at O’Hare. Bennett was awestruck when he caught up to William “Refrigerator” Perry, who put his arm around Bennett and imparted sage words of advice:

“Live your dreams, kid. Be yourself. Everything is possible. If you want it. Do it. Like I did.”

“In my mind, he told me to move to America,” Bennett said. “I think in his mind, he spoke every cliché an athlete tells a kid when they want to get away from them. So right after I finished university, I moved to Chicago [in 1993], came on a tourist visa and simply never left.”

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Bennett first lived in Hyde Park, where he worked the early shift as a baker, was a librarian in the afternoon — “I’d sleep in the stacks” — and waited tables at night. In search of a change of scenery, he looked at a map and saw Rogers Park. Seeing that he shared the neighborhood’s name, he moved there.

While living on the South Side, Bennett became a White Sox fan. He adored Harold Baines and fell in love with baseball, which he called “chess with chewing tobacco.” He goes back as often as he can. In August 2019, Bennett brought his children to a Sox game and threw out a ceremonial first pitch.

Even in New York, he’s still immersed in Chicago sports.

“As I’m speaking to you, above my television set, I’ve got a painting of Walter Payton, I’ve got my signed Joey Cora Chicago street sign, I’ve got a hilarious photo of Mike Ditka flipping the bird walking off the field after a loss,” Bennett said. “I’ve got my Steve Stone-signed baseball, right by my Hank Greenberg- and Sandy Koufax-signed baseballs, and he signed it ‘Steve Stone, the other Jewish Cy.’ ’’

In the Premier League, Bennett is a lifelong supporter of Everton, the other team in Liverpool. The teams have a Cubs-Sox dynamic, and Bennett’s team is the Sox equivalent. But that’s exactly what he wants in his teams, and the Bears make for a perfect match.

“Being a Chicago Bears fan prepares you for life,” Bennett said. “Life is dark, it’s full of challenges, there’s a lot of suffering, and when you win something beautiful, you never take it for granted. I say sometimes I don’t know where the Everton ends and the Chicago Bears begins.”

But he does know how he feels about a city where he spent a small part of his life, yet it shaped his life.

“I did tell myself in the dark times, when things were terrible at school, it didn’t matter, I should be in Chicago,” Bennett said. “America saved my life; Chicago saved my life. Chicago is very much who I am. It’s who I wanted to be. It’s who I became.”