The city of Chicago’s sports fans are absolutely buzzing right now.
Their beloved Chicago Bears NFL franchise secured its first playoff win since 2011 when they defeated their bitter NFC North divisional rival Green Bay Packers by a score of 31-27 on January 10. Star quarterback Caleb Williams overcame a tough start to the game (the Packers were winning 21-3 at halftime and 21-6 after three quarters) and led the Bears to a memorable comeback, finishing with 361 yards, 2 touchdowns, and 2 interceptions on 24 of 48 attempts.
Jan 10, 2026; Chicago, IL, USA; Chicago Bears quarterback Caleb Williams (18) rolls out as Green Bay Packers linebacker Quay Walker (7) applies the pressure during the first half of an NFC Wild Card Round game at Soldier Field. Mandatory Credit: Matt Marton-Imagn Images | Matt Marton-Imagn Images
And this wasn’t the only awesome news that Chicago sports fans received on Saturday night, as news broke that three-time All-Star and two-time World Series winner Alex Bregman signed a five-year, $175 million contract with the Cubs.
This is arguably the biggest signing in franchise history, especially because Jed Hoyer and the rest of the Cubs’ front office and ownership have gotten a lot of flak for not securing top free agents in recent years. But now that narrative can be put into the rearview mirror, as Bregman was one of the best free agents available entering this offseason.
Mar 28, 2025; Arlington, Texas, USA; Boston Red Sox third baseman Alex Bregman (2) reacts during the game against the Texas Rangers at Globe Life Field. Mandatory Credit: Kevin Jairaj-Imagn Images | Kevin Jairaj-Imagn Images
Alex Bregman joins Chicago Bears celebration after Cubs signing
In the moments after Bregman’s signing was announced, his wife, Reagan, posted a photo to her Instagram story that showed her and Bregman toasting what appears to be spicy margaritas at a restaurant. The story is captioned, “Proud ❤️”.
While this was a nice sentiment, Bregman’s first Instagram story in the wake of his Cubs signing was more about Chicago’s NFL team. He posted a Bears flag that had the iconic “DA BEARS” tagline on it.
Alex Bregman IG Post | Alex Bregman / @abreg_1 / Instagram
As if Bregman couldn’t be any more popular in the Windy City right now, this is surely to further endear him to the Bears faithful.
It will be fascinating to see what Chicago’s next moves are with Bregman now on board. In structuring their infield, the two options appear to be either trade Nico Hoerner and move Matt Shaw to second base or keep Hoerner and turn Shaw into a super-utility type player, where he can fill in at multiple positions in case a player gets hurt or needs a day of rest.
But Chicago fans don’t need to worry about that right now. Instead, they can bask in the Bears’ big victory and feel good about the Cubs signing Bregman in free agency and trading for Edward Cabrera earlier this week.
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