Chicago Bears Chairman George McCaskey was signing autographs Sunday at Wrigley Field before his temporary gig as a celebrity umpire for the Savannah Bananas game.
One guy was booing him for reasons you might suspect, but otherwise he was welcomed by the family-friendly crowd, which obviously included many Bears fans. People are usually much nicer to an owner in person than on the internet, where the man who runs the Bears has taken his lumps over the last several years because of bad management by his organization.
Maybe it was because the Bears are winning, with a real top-10 quarterback and a coach who knows how to coach. Or maybe the kids didn’t know who he was and figured he was part of the Banana Show.
Whatever the reason, it had to be a good feeling for McCaskey to finally get his flowers.
Now let’s see if Jerry Reinsdorf and Tom Ricketts will get theirs.
The chairmen of the White Sox and Cubs, respectively, Reinsdorf and Ricketts find themselves in similar positions as next Monday’s trade deadline nears.
Both teams are in contention. Both are in drastic need of pitching. Both have fan bases that are skeptical of ownership’s willingness to go the extra mile to compete for a World Series title.
All of the focus in the next week will be on Cubs President Jed Hoyer and White Sox general manager Chris Getz, but it’s Ricketts and Reinsdorf who really hold the cards.
They’re the ones who have final say on how far their executives can go to add the right pieces, whether it’s two-month rentals who likely will be gone after the season in free agency or players with another year or more on lucrative contracts. No matter how much they insist they let the executives do their jobs, all Sox fans know that Reinsdorf never has given out a nine-figure contract to a player, while Ricketts hates paying the luxury tax.
Neither subscribes to the philosophy of Philadelphia Phillies owner John Middleton, who in 2018 said they had to “maybe be a little bit stupid” in spending on free agents.
“Intelligent spending” was the Cubs’ mantra when they came out of the rebuild in 2023, signing Dansby Swanson, Cody Bellinger, Jameson Taillon and Eric Hosmer, who didn’t last a season. Bellinger was re-signed before the 2024 season but was dealt to the New York Yankees after the season in a salary dump, while Taillon was designated for assignment Monday after his struggles became too great for manager Craig Counsell, who pulled the plug on him as a starter.
The Cubs’ trade-deadline haul last year was underwhelming, but Hoyer argued that few of the top available pitchers were dealt. Now he’s in the same situation, and dumping Taillon means they might need two starters instead of just one.
Ricketts already spent to win in 2026, paying free agent Alex Bregman $175 million for five years over the winter. The Cubs are eighth in the majors with a $233.3 million payroll, according to spotrac.com, nearly $100 million more than the division-leading Milwaukee Brewers. They have by far the most resources of any National League Central team and already have gone over the tax threshold.
The Cubs aren’t close to the Los Angeles Dodgers in spending and never will be. Ricketts told The Score last year that Cubs fans “think somehow we have all these dollars that the Dodgers have or the Mets have or the Yankees have and we just keep it. Which isn’t true at all. What happens is we try to break even every year, and that’s about it.”
He later retracted the “break even” remark, but the reputation as an owner who will spend just enough to win without going overboard remains intact.
Frugal spending has been the Sox’s preferred strategy, exacerbated by the latest rebuild. Their $90.7 million payroll ranks 28th, third-lowest in the majors. Their closest competitor in the American League Central is the Cleveland Guardians, who are last at $73.2 million.
Reinsdorf can point to the Sox payroll and argue he’s doing it the right way: investing in a farm system instead of risky free agents and competing at the same time. He has to decide whether it’s the right time to invest in a high-priced starter to try to get them over the hump or to make smaller, cheaper moves such as Sunday’s acquisition of Jose Urquidy.
The Sox have enough talent in the system to get a frontline starter, but no one knows whether Reinsdorf has the appetite to spend on one, even as a rental.
Garrett Crochet, Dylan Cease, Chris Sale and Carlos Rodón are prime examples of elite starters who were traded or left the organization because the Sox weren’t willing to risk long-term deals on them. I can even go back to Jack McDowell and Alex Fernandez when I was on the Sox beat back in the mid-’90s.
It’s a Sox thing.
But Reinsdorf, 90, is not getting any younger and already has a succession plan in place that eventually would deliver the Sox to billionaire Justin Ishbia, who is expected to operate them like a major-market team. Reinsdorf can sell the team between 2029 and 2033, and if not, Ishbia has the option to buy it after 2034.
Reinsdorf won’t talk on the record, but his friends insist he desperately wants to go out a winner. How far he’s willing to go to do that remains to be seen. When the Sox started their previous rebuild, he told USA Today’s Bob Nightengale in 2017 that the decision was “tough, very tough.”
“What made it hard for me was my age,” he said. “I’m 81 years old. How long am I going to be around, right? So why would I want to go for a full rebuild at my age?
“The decision I made was that I can’t be a factor in this thing. As the owner of this team, I have an obligation to do what’s right for the fans. The real owner of a team is the fans; the owner is a custodian. I will be gone one day, but fans will still be there. So you’ve got to run the team (the way that’s) right for the fans and not even think about how old I am.”
That rebuild peaked with the 2021 playoff team and fizzled out by the next season. Reinsdorf had installed Tony La Russa as his manager after the 2020 season ended in the wild-card round, bypassing the advice of executives Ken Williams and Rick Hahn, who were fired in August 2023.
It was all downhill until this season, when the signing of Munetaka Murakami and the development of Colson Montgomery, Miguel Vargas, Grant Taylor and others have helped get the Sox a few games over .500, which just might be enough to win the AL Central.
Nine years after saying he won’t be around forever, Reinsdorf is still around. It only seems like forever after three straight 100-loss seasons.
This could be Reinsdorf’s last chance at an October run. Progress isn’t always linear in a rebuild, as we’ve seen in the downward spirals of the Baltimore Orioles and Kansas City Royals. The 2027 season isn’t guaranteed because of the expiring labor agreement. If not now, when?
If Reinsdorf still believes he has “an obligation to do what’s right for the fans,” he has no choice but to add a frontline starter, no matter the cost.
They’re not getting any younger either.
