Roger Bennett had to see Chicago Bears quarterback Caleb Williams in person. Bennett has been a Bears fan for 45 years, but he knew this season opener was special.
“I try to resist the urge to be hyperbolic and knee-jerk, but I did feel the need — like a salmon swimming upstream — to be at Soldier Field for the opener,” Bennett said. “I thought we finally got a Sid Luckman replacement. It’s taken 74 years since he left us, but we got it.”
Bennett, the founder and CEO of the Men in Blazers Media Network, could only have dreamed of this opportunity when he grew up in Liverpool, England. There he was, standing on the Soldier Field grass before the game, about to take in the twists and turns of the Bears’ season-opening win.
“I did feel like when I went to the season opener … I think I was going to witness the coronation of a young king,” he said. “I didn’t know what I was expecting that day. I do remember the first snap and I expected it to be like watching Mozart just rip off a concerto each day, Bobby Fischer to just checkmate me in four, or Lil’ Bow Wow drop his debut album.
“Like, oh my God, prodigy from the off.”
As the Bears prepare to face the Jacksonville Jaguars at Tottenham Stadium on Sunday, Bennett — one of the most well-known Bears fans, American or British (and Bennett is British-American after becoming a U.S. citizen in 2018) — told The Athletic the story of his Bears fandom, which began in Liverpool and traces back over a century. Yes, a century.
Hello Beautiful Chicago. Here to witness beginning of Bears Dynasty with my own eyes. The Bad Man has gone. What can possibly go wrong now? 🐻 ⬇️ pic.twitter.com/YWjqLO7dQ5
— roger bennett (@rogbennett) September 10, 2023
Through “Men in Blazers,” the largest soccer-focused media company in North America, Bennett has studied Americans who have become fans of the English Premier League.
“Their knowledge is as deep as English fans,” Bennett said. “Their understanding of the game becomes as deep. But for many of them, they don’t have the geographical connection and they don’t have the multi-generational inheritance. They’re choosing freely.”
That might sound like how Bennett would’ve discovered the Bears in the 1980s. And in a way, it is. Like many who lived in the United Kingdom that decade, when Channel 4 started to show NFL highlights on Sundays, Bennett gravitated to the Bears. But this was more than falling in love with the “Monsters of the Midway” for their football prowess.
“I always saw myself as a kid as a Chicagoan trapped in a Liverpudlian body,” Bennett said. “The Liverpudlian was probably the mistake. The Chicagoan was the actuality.”
The myth in the family is that Bennett’s great-grandfather, a kosher butcher, left Ukraine on a boat headed to Chicago. But when the boat refueled in Liverpool, they saw one tall building and assumed it was New York. They got off and began their new lives.
“And so we were trapped in Liverpool, a whole family for multiple generations,” Bennett said. “But the lure of Chicago never left us.”
Bennett grabbed a small figurine of the Empire State Building he has on his desk, one that his grandfather gave him when he was a child. Bennett would learn about America from his grandfather, who traveled there often.
“I was always fascinated by this place, this magical place that existed in color, technicolor, really, whereas my life was lived in black and white,” Bennett said.
Liverpool is “a magnificent city,” Bennett said, but the ’80s were “a very dark time for the whole north of England.” Bennett continued to fantasize about the United States, and then he started watching American football on television.
“We’d never seen anything like it,” he said. “It was joy. It was kinetic. When you were losing, there was joy and humor in it.”
Already a fan of Chicago from afar, Bennett naturally gravitated to the Bears. It was 1984. They were one of the best teams in football and about to embark on one of the greatest seasons in NFL history.
“The timing was just unbelievable,” Bennett said. “Kids follow superheroes. William ‘Refrigerator’ Perry was that to me. He could do it all. Enormous man with soft hands, pace, power, a smile.”
A chance meeting at the park that summer set Bennett up to live out this fantasy. He met a boy who was from Northbrook, Ill., and for two weeks, they played together at the park and became friends, then when that boy went back home, they became pen pals. Bennett would receive posters of the Bears and newspaper clippings about the eventual Super Bowl champs.
To truly experience the ’85 season, Bennett and his friend Jamie would randomly call phone numbers with a 312 area code. Because the NFL highlights show in the UK aired a week later, it was the only way to get anything “live.”
“God bless the people of Chicago,” Bennett said. “We’d keep them on for 30, 40 minutes. They’d be like, ‘You know, it’s second-and-7, Jim McMahon rolls to the right.’ They gave us commentary on the phone. Long-distance bills were enormous, and that’s how we keep going.
“I remember when they lost to Miami, it felt like a funeral. This thing that had nothing to do with me that no one else knew about, it was humanly devastating. It was my Waterloo in many ways.”
Bennett was a die-hard fan, both of the Bears team, but also of this city that has, in a way, been in his family for generations. The pen pal then invited Bennett to stay with his family in the Chicago suburbs during the summer of 1986.
And wouldn’t you know it, Bennett and his beloved Bears were on separate continents, again. The Bears had gone to Wembley Stadium in London to play in the first American Bowl.
“I was seething,” he said. “I had come to where they meant to be, they had gone to where I was. There were photos of Walter Payton joking around with Phil Collins’ son. I had never hated Phil Collins more than I did at that moment. I was so happy it rained during the American Bowl so everyone looked miserable.”
When the broadcaster said the Bears would fly home immediately after the game, Bennett convinced his host family to go to O’Hare to meet his heroes.
While some players, and coach Mike Ditka, had no time (or patience) for Bennett and his friends (“As if there were thousands of people thronging,” Bennett said. “There was like four little kids”), Payton did stop for photos.
Unfortunately, the shutter on Bennett’s old camera jammed.
“I don’t have many regrets in life,” Bennett said, “but not getting a picture with Walter Payton definitely top four all time.”
The moment that stuck with Bennett forever, and ultimately inspired him to write his book, “(Re)Born in the USA,” was when “the Fridge” walked off the plane.
“He put his arm around me, whispered in my ear — had quite a sweet, high voice that was quite surprising — and he said, ‘Dream big dreams, kid. I did, and you can, too,’” Bennett said. “At the time, I mean, my God, I meditated on that for about a year. In my head, ‘The Fridge’ himself was telling me to move to Chicago.
“I am here, to this day, because ‘The Fridge’ told me I should take a leap into the unknown.”
Less than a decade later, Bennett moved to Chicago — Rogers Park, of course. He spent a few years in Chicago before moving to New York — a die-hard Bears and White Sox fan in New York City.
“I feel so close to Chicago and the Bears truly did animate me, and the fact that I met them and erroneously believed William “Refrigerator” Perry told me to move there, means that they’re so deeply formative,” Bennett said.
Thread: The Chicago Bears in general, and William Refrigerator Perry in particular, changed my life. Fridge was a defensive lineman who could run the ball on offense and catch touchdowns. He’s also major reason I moved to America. I wrote a book about it 🇺🇸
Here’s the story 1/ pic.twitter.com/wrZfUCCLCK
— roger bennett (@rogbennett) May 6, 2021
Growing up in Liverpool, Bennett became a fan of Everton Football Club. That’s his geographical team, the other one he follows religiously.
Everton and the Bears have some similarities. The Toffees were a founding member of the Football League, and the Bears were the charter franchise of the NFL. Everton’s last championship in the top tier came in the 1986-87 season, right after the Bears’ only Super Bowl victory. As the Bears have spent the past decade-plus without a playoff win, Everton has escaped relegation the past three seasons.
(One thing Everton does have over the Bears is construction is well underway on their new stadium).
“Sometimes I don’t know where my Chicago Bears end and my Everton begins,” Bennett said. “You’re catching me off a very odd weekend when both teams won, and I don’t know what to do with my hands.”
To Bennett, being a devoted fan of both is the epitome of what being a sports fan is all about.
“There’s definitely a shared sense of self-sabotage, of self-destruction,” he said. “We are all collectively on the march of folly of, what could you do? And I think it’s magical. I wouldn’t want it any other way.”
Brutal time to be an Everton and Chicago Bears fan. Fell in love with Bears in 1984. Season later, Everton won league, Bears won Super Bowl. Now both have fired their coaches within a week and have owners who only seem to do right thing by accident. Where Hope and Pain collide
— roger bennett (@rogbennett) January 16, 2022
Bennett’s wife, Vanessa, will ask him, “Why did you do this?” as their four children have picked up his passion for Chicago teams that haven’t been very successful.
“I do think a lot about it, and I think that both the Bears and Everton Football Club can teach you a lot about life,” he said. “Life is hard. Life is full of challenges. The world is dark and filled with chaos. And Everton and the Bears are reflections of that reality.
“What I think Everton and the Bears teach you … the secret of sports fandom and the secret of life itself is that when you have a happy moment, treasure it, savor it with those you love and always dance as if you were at your own kid’s wedding. I believe that absolutely and completely. So in many ways, I’m very grateful to both of those teams for reinforcing that.”
Bennett won’t make the trip to London this weekend. The United States men’s national team has its first match under new manager Mauricio Pochettino.
Tottenham’s stadium, Bennett says, is “remarkable … it’s a slice of America in England.” He enjoys when a camera pans the crowd at London games, seeing the fans in a variety of NFL jerseys, regardless of who’s playing in front of them.
“The thing that’s beautiful about the (NFL) fandom in England is why I love soccer fandom in the United States: It is shorn of territory,” he said. “There is a mutual joy of self-discovery.”
Bennett has a signed football from Super Bowl kicker Kevin Butler. He talks in revered terms about Super Bowl punter Maury Buford. And when it was time to make his annual purchase of a Bears uniform, Bennett didn’t go with No. 18. He went one higher — No. 19, punter Tory Taylor. And Bennett spoke about Taylor as only Bennett can, another example of what the Bears mean to him.
“Can we just say he is electric?” Bennett said. “Punting is meant to depress the hell out of you as a fan. There’s failure. It’s darkness. Fear kicks in. You’re deflated. But Tory Taylor comes on, and let’s just say it’s a bit like … I read that Luther Vandross once sang backup vocals for Ringo Starr. Hang on, in your own right, you’re bloody Luther Vandross, what are you doing singing backup? Tory Taylor is just like, he comes on, it’s like the backup singer grabs the microphone and says, ‘All eyes on me.’
“I’m so pumped every time we punt. I live for punt and pins. I should put that on a T-shirt, ‘I live for punt and pins.’ But it’s transcendent.”
(Top photo courtesy of Roger Bennett)
