When the Chicago Cubs announced that they had signed third baseman Alex Bregman to a 5-year $175 million contract, I was ecstatic and began counting down the days to Spring Training. Like many Cub fans, even many non-Cubs fans, the offseason had not delivered any of the high-dollar free agents to a destination, and I was frustrated with the lack of any substantial improvement to the lineup.

The Bregman signing signals to Cubs fans that the team is all in for 2026 and serves notice to the league that the club is willing to spend when the right player comes along at the right time.

When I sat down to write about Bregman, however, I was reminded that he was at the center of the scandal that rocked Major League Baseball after the 2017 World Series, which the Astros won but which was stained by the sign-stealing allegations, which were later proven to be valid.

Bregman was roundly booed at every road stadium after the league punished the Astros as a team, but did not hand out any individual punishments. I remember. As a Yankees and Cubs fan, I booed.

Bregman is one of the few Astros players to offer a public apology. He stood with Jose Altuve and Astros Chairman Jim Crane and read a prepared statement expressing remorse for his actions and the impact they had on fans and on baseball. Chandler Rome of The Athletic wrote that Bregman was “the closest thing Houston has to a clubhouse spokesman,” “The Evolution of Alex Bregman: the once brash third baseman enters platform year ‘ at peace,’” 3/27/24.

The Cubs haven’t weathered a scandal the size of the Astros, but they have had their share of trouble, particularly during the steroid era when Sammy Sosa became the focus of longstanding speculation about possible steroid use, not to mention his suspension for using a corked bat.

Unfortunately, Sosa’s spectacular career in Chicago ended on a sour note in 2004 when he failed to make himself available during the final game of the season and reportedly left Wrigley Field before the game was over.  It would be 21 years before he set foot in Wrigley Field again.

Over the years, fans clamored for Sosa’s return, but the club insisted Sosa had work to do, particularly accepting responsibility for his alleged steroid use. Sosa issued an apology (not an admission) in December of 2024 and was reconciled with the team, making a huge splash at 2025’s Cubs’ Convention.

“The Cubs Way” has become distinctive in the league in recent years, thanks, to a large degree, to Tom Verducci’s Book The Cubs Way: The Zen of Building the Best Team in Baseball and Breaking the Curse. Verducci details the emphasis the Cubs placed on personal character and conduct when drafting and acquiring players while Theo Epstein was President of Baseball Operations for the Cubs from 2012-2020 (current President of Baseball Operations, Jed Hoyer, was his General Manager).

Under Hoyer’s tenure, the Cubs recently outbid the league for shortstop Dansby Swanson. Four of the league’s top shortstops were available after the 2022 season: Carlos Correa, Dansby Swanson, Trea Turner, and Xander Bogaerts. Matt Ostrowski of North Side Baseball wrote that the Cubs were impressed with Swanson’s intangibles: his intelligence about the game and his leadership in the clubhouse while in Atlanta. Matt Ostrowski, “Like Dansby Swanson, Alex Bregman was always Cubs’ top target,” North Side Baseball, 1/12/26.

Bregman, like Sosa, has had to rebuild his public image to regain the respect and appreciation of fans.  The Cubs clearly value intangibles, and Bregman has plenty to offer.

He is obsessively devoted to the batting cage, daily routines, and detailed preparation. Bregman has evolved from the brash, showboating player he was in Houston (but he did sport an 8.9 WAR in 2019) to a more cerebral and respected mentor to other players.

The Cubs clearly believe the 31-year-old Bregman will age gracefully. He doesn’t hit the ball harder or farther than other players, but he knows how to win. He said, “I’ve always put everything I have, every ounce of energy into the game every single year” Chandler Rome, “The Evolution of Alex Bregman,” The Athletic, 3/27/24. The Cubs are counting on Bregman to bring heart and soul to winning in the Windy City.