On January 10, the Chicago Cubs signed three-time All-Star third baseman Alex Bregman, who was a free agent after his 2025 campaign with the Boston Red Sox. Immediately following the signing, the Chicago Bears completed their largest comeback in postseason history, defeating the Green Bay Packers to advance to the divisional round. The Chicago Bulls and Blackhawks also scored victories, making January 10 one of the most significant days in recent Chicago sports history.
The Cubs gave Bregman the third biggest contract in team history, signing him for five years and $175 million placing just behind Dansby Swanson’s $177 million contract and Jason Heyward’s $184 million contract in 2018. However, Bregman’s is the largest by average annual value, as he will make $35 million a year. Historically, Bregman has been one of the best third basemen in the MLB, making nine straight playoff appearances alongside with making seven straight American League Championship Series from 2017 to 2023. He won two World Series, both with the Houston Astros, in 2017 and 2022.
Bregman’s signing is a significant one for the Cubs. Last season, they brought in a different Astros star, Kyle Tucker, and he had an impressive 2025 campaign, leading the Cubs to the playoffs. Before the Bregman signing, the Cubs signed star pitcher Edward Cabrera from the Miami Marlins, where they gave up their top prospect, outfielder Owen Cassie, along with two other prospects, in exchange for the ace.
Many Cubs fans thought the team overpaid for Cabrera, and that the trade was not worth it, especially considering that Tucker was likely to leave and with trade rumors swirling around second baseman Nico Hoerner. The consensus among Cubs fans was that this was largely a good trade, provided the Cubs signed a big bat. They did exactly that. Bringing in Bregman fills the void that Tucker will likely leave, and the rotation gets a lot better with the signing of Cabrera. The Cubs are looking to win right now, and they are spending the money that fans have been begging for in the past years.
In a very young Cubs lineup, Bregman is a veteran presence with great clutch ability and Gold Glove caliber defense at the hot corner (he won the award in 2024). Last season, the Cubs won the National League Team Gold Glove Award, and are well-positioned to repeat with this addition. If the Cubs can keep the same lineup and starting rotation as last season, minus Kyle Tucker, they will go into 2026 looking like one of the best teams in the MLB, flush with stars like Pete Crow-Armstrong, Michael Busch and Ian Happ, alongside pitchers like Justin Steele, a young arm in Cade Horton and now Edward Cabrera.
With a deep playoff run, this could define a new era of Chicago Cubs baseball since the last time they last stood on top in 2016. Young talent combined with veteran strength could be the key to another championship for a historic franchise.
With an arguably worse roster making it to the division series last year, who knows what is in store for the Cubs in this 2026 season. It looks like every Chicago sports team is on the rise, and that could all be due to the signing of Alex Bregman during the Bears magical comeback. The Cubs aren’t planning on tomorrow; they are betting on today.