Paul Sullivan: Can the new face of the next generation of McCaskeys save the Bears?
Published in Football
CHICAGO — Some big news out of Halas Hall last week was buried on a day when Chicago Bears Chairman George McCaskey and President/CEO Kevin Warren updated the stadium plans and coach Ben Johnson announced he wouldn’t play Caleb Williams or most other starters in a meaningless preseason opener.
Edward L. McCaskey was named to the seven-member Bears’ board, replacing his grandmother, the late Virginia McCaskey, and becoming the first member of the next generation to be part of running the $6 billion franchise founded by his great-grandfather, George Halas.
No reason was given for the appointment other than George McCaskey calling him “my favorite nephew,” which is as good a reason as any when it comes to hiring in Chicago. Edward is the son of board secretary Patrick McCaskey, and was named after Virginia’s late husband and former Bears Chairman Ed McCaskey.
“I told him: ‘You have big shoes to fill, kid,’” George said on Friday of his nephew, who is in his late 30s. “He has been fantastic so far. He’s bright. He’s articulate. He asks great questions. He’s eager to learn. And it’s exciting to have the next generation of our family on the board.”
This is exciting stuff for Bears fans, who’ve been waiting on the next generation of McCaskeys to reverse the stagnation of the franchise under the current generation of McCaskeys. It’s a thankless task, but someone has to do it since George once said the McCaskeys won’t sell the team “until the Second Coming.”
I don’t know anything about Edward’s qualifications to serve on the board, or which cousins were runners-up for the board seat. But I’m rooting for him to succeed because it’d be a great sports story. According to McCaskey’s LinkedIn profile, he’s an internal wholesaler and a former Bears ball boy, summer intern with the NFL, sports information assistant at Wheaton College, director of marketing for the Schaumburg Boomers and media relations director for the Gary Southshore RailCats.
Taking over the Bears someday should be a piece of cake. Maybe he can even cut a stadium deal in the late 2040s and get them out of an outdated Arlington Heights stadium his Uncle George built in the late 2020s.
In a Chicago Tribune profile in 2011, when he worked for the RailCats, Edward said he wanted to be judged on his own merits and not for his Bears connection.
“I want people to know me for me, not just a name,” he told former Tribune columnist David Haugh. “It was a struggle in high school (Loyola Academy) to make real genuine friends because it was, ‘You’re the kid who owns the Bears.’ I don’t mind taking a backseat.”
His father and uncles George and Brian aren’t getting any younger, so eventually Edward can move into the front seat, perhaps as the driver. Chicago’s history of sports owners handing down the reins to heirs is deep … and mostly comical, if you enjoy laughing through the pain.
But we do have precedent when it comes to nepo owners undoing their dad’s deeds for the betterment of the team.
Late Blackhawks owner Rocky Wirtz succeeded his father, William Wirtz, after the man nicknamed “Dollar Bill” died in 2007. Rocky put the Hawks’ home games on TV, hired past Hawks legends as ambassadors, brought back popular play-by-play man Pat Foley and helped steer the organization through three Stanley Cup-winning seasons in the 2010s.
The Hawks were in a rebuild when Rocky died in 2023. Rocky’s son, Danny Wirtz, succeeded him and became the latest face of the family-owned franchise, which dates back to Arthur Wirtz’s purchase of the team in 1946.
Danny was named interim president and CEO in 2020, so at least he had a running start by the time Rocky died. He also had a marketing background as director of sales for Wirtz Beverage Group, and once worked as a band assistant to Ministry during a tour in 1999.
These life experiences can only help as he tries to return the Hawks to relevance in the 100th anniversary of the franchise.
“(Rocky) didn’t like waiting around or overcomplicating or bureaucracy,” Danny told the Tribune’s Phil Thompson in 2023. “I do like process. I like strategy. I like planning but with the same end goal in mind.”
Despite the best-laid planning and strategy, the Hawks’ rebuild remains a work in progress, much like the Bulls’ rebuild, which is being run by another future nepo owner, Michael Reinsdorf, son of Bulls and White Sox Chairman Jerry Reinsdorf.
Michael became president of the Bulls in 2010, when Jerry felt like he’d been letting the team run on autopilot.
“I under-managed the Bulls, I really did,” Jerry Reinsdorf told ESPN’s Melissa Isaacson in 2012. “That was one of the reasons for wanting Michael in here. I found myself letting the Bulls succeed on their own. We had a successful business, we’re doing well financially and I sort of let it slide.
“I just felt we needed another person there to take us into the future and not just rely on our past success. Also, young people need to run businesses because there’s so much they know that I don’t with digital marketing and brand building, the Internet. It was time for that to happen with the Bulls.”
The Bulls have remained a successful business financially, but haven’t had much success on the court, with one Eastern Conference finals appearance in his first season, seven postseason appearances in 15 seasons and only one postseason team since 2017-18.
At least Jerry has opted to sell the White Sox to an outside interest in billionaire Justin Ishbia, allowing Michael to give his undivided attention to the Bulls and allowing Sox fans to dream of a competitive, big-market type of payroll.
Cubs fans who aren’t satisfied with current ownership probably won’t be any happier if Chairman Tom Ricketts one day turns the team over to one of his five kids, or various nieces and nephews of co-owners Todd Ricketts and Laura Ricketts. But Tom said in 2013, “it just feels like (the Cubs) would be a family business forever,” so don’t be surprised if the next generation of khaki-wearing Rickettses takes control.
The Cubs have a storied history of nepo babies taking over since chewing gum magnate William Wrigley handed the team down to his son, Philip K. Wrigley, in 1932. P.K.’s son, William, took over upon his father’s death in 1977 until selling it in 1981 to Tribune Co.
The common denominators of the Wrigley family’s six-decade reign were no championships and no lights at Wrigley Field. But at least they didn’t tear down Wrigley Field, which is now a year-round ATM machine for the Rickettses and a tourist destination for baseball fans.
Nepo owners in Chicago have had their ups and downs. So will Edward L. McCaskey’s journey from Bears ball boy to Bears owner come to fruition?
We can only watch and wait, same as the Ben Johnson era.
But if the face of the next generation of McCaskeys manages to win even one Super Bowl, he’ll at least be ahead of Uncle George.
So bear down, Edward L.
Bears nation turns its lonely eyes to you.
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