The Chicago Cubs celebrate their 150th anniversary this season, beginning with this weekend’s annual convention at the Sheraton Grand Chicago.
To put things in perspective, the president when the Cubs first took the field in 1876 was Ulysses S. Grant, who helped end the Civil War instead of trying to start one. And the telephone had just been invented that year, so few could call the Chicago Tribune and complain about not having the Cubs score in their edition.
Anyway, it’s being called a “very special” weekend and a joyous time for Cubs fans, coming off an actual playoff appearance in 2025 and with budding stars such as Pete Crow-Armstrong, Michael Busch and Cade Horton back and ready to take that next step.
Manager Craig Counsell also will be on hand, and according to a press release, fans can “mingle and enjoy a beverage with Chairman Tom Ricketts!” (The exclamation point is mine).
All in all, it’s certain to be a memorable weekend, thanks mostly to the recent signing of third baseman Alex Bregman and the return of the 2016 Cubs to celebrate the 10th anniversary of their championship season. That was supposed to be the start of a Cubs dynasty that never was, ensuring players would never have to buy a drink in this town for the rest of their lives.
They remain beloved despite their failure to add titles, and the addition of Bregman, like the signing of Jon Lester in 2014, is expected to bring back the vibes that led to a brief Golden Age of Cubs baseball.
The Cubs invented the fan fest 40 years ago, and I’ve been assigned to cover most of them since the second one in 1987, when the hot topic was whether they would sign Andre Dawson. The concept back then was simple — keep the Cubs on the minds of their fans 365 days a year instead of from spring training through September.
“We wanted to market the product 12 months a year,” former Cubs executive John McDonough once said of his invention. “Beforehand, once the season ended, it got dark and you’d get ready for next year. We wanted to perpetuate everything.”
It worked, and the Cubs have used it to introduce new players, managers and executives, to bring back familiar faces and to spread hope that this year would be better than the last. It’s a time-honored concept that seldom strays from its roots, marking the unofficial beginning of the baseball season and giving fans a chance to dream — or complain, depending on the offseason moves.
Jed Hoyer, from left, Randy Bush, Theo Epstein and Scott Harris participate in a Q&A during the Cubs Convention on Jan. 13, 2018, at the Sheraton Grand Chicago. (John J. Kim/Chicago Tribune)
President Jed Hoyer, who served as the proverbial potted plant alongside then-President Theo Epstein at Q&A session in his first nine conventions, is beginning his 15th season in Chicago, having outlasted most of the reporters covering the team.
But those of us who remain know Hoyer is smart enough to realize he can go most of the winter without making a splash as long as he does something before the Cubs Convention. This season he followed the script perfectly, getting the Bregman deal done before the buzzer.
So instead of being booed for trading top prospect Owen Caissie, Hoyer is expected to be applauded for giving Bregman a five-year, $175 million deal that solidifies the Cubs lineup in the absence of Kyle Tucker, the star of last year’s Cubs Convention who remains unsigned. Had Hoyer waited another week, he would’ve been asked incessantly about why he didn’t get another bat. Instead, he’ll get many compliments on his socks — and for getting Bregman.
The Bregman signing was leaked during the third quarter of the Bears’ miraculous comeback win over the Green Bay Packers in the wild-card round Saturday at Soldier Field, a curious bit of timing that no one could process until the smoke cleared. You’d think the Cubs would want to have at least one news cycle during which a $175 million signing was the biggest sports story in town.
Oh, well. They plan to introduce their new star Thursday at the Cubbieplex offices next to Wrigley Field, so at least they’ll be able to get some attention before Bears Fever cranks up again for Sunday’s divisional-round game against the Los Angeles Rams.
Epstein used to caution the media about the risks of signing free agents past age 30 to long-term deals, but Hoyer had no qualms giving the 31-year-old Bregman five years and a coveted no-trade clause. According to the Boston Globe, the Red Sox felt confident they were going to bring Bregman with a five-year, $165 million deal and were wary of bidding against themselves.
Red Sox third baseman Alex Bregman, right, celebrates after his home run against the Yankees on Sept. 13, 2025, in Boston. (Mark Stockwell/AP)
Kudos to Hoyer for getting Ricketts to cave in and give Bregman more money and the coveted no-trade. We’ll have to assume Ken Rosenthal’s constant needling of Ricketts in The Athletic, calling him a cheapskate owner of a major-market team, finally did the trick.
If Bregman is healthy, he should provide the kind of offense the Cubs got from Tucker in the first half of 2025 before Tucker’s injuries led to a power outage and a mediocre playoff performance. Bregman is well respected in the clubhouse and should be beneficial to the careers of Crow-Armstrong, Busch and other young players.
“He was one of the guys that I could depend on to send a message and I don’t have to tell him what message to send,” former Houston Astros manager Dusty Baker once said. “This is what I love about Bregman.”
The taint of being part of the cheating 2017 Astros has worn off over the years, and Cubs fans are banging the drum for Bregman’s arrival, excited to have an offensive upgrade from Matt Shaw, who can still learn a lot from playing multiple positions and watching from the bench. That’s assuming the Cubs don’t move him to second and trade Nick Hoerner, which would be the worst move by the organization since dealing Mark DeRosa and then signing Milton Bradley after the 2008 season.
If Bregman doesn’t work out, we might not see another megadeal from Ricketts for a long time. That’s a lot of pressure to put on one player, but seemingly he’ll be able to able to handle it.
Meanwhile, the 150th birthday party officially begins. There really hasn’t been much to celebrate since 1876 with one World Series win in our lifetime and only three in their entire existence. But I’m confident the Cubs will find a way to spin it so they look like the New York Yankees.
That’s the real Cubs Way.