Cubs could eye Alex Bregman and Dylan Cease this offseason, two high-impact free agents who could catapult them into World Series contention.
The Chicago Cubs don’t appear to be the favorites for many of the top free agents this winter, according to MLB.com.
They recently put together an article predicting where the top free agents might sign this offseason. 46 different voters determined where free agents like Kyle Tucker, Framber Valdez, and Dylan Cease could sign in the coming months.
Of the top 13 free agents that MLB.com highlighted in the article, Chicago was only listed as a top-3 favorite for Alex Bregman and Dylan Cease.
The Cubs received the third-most votes that Bregman would sign with them this offseason (7%), behind the Red Sox (43%) and the Tigers (37%). The Cubs then received the second-most votes for Cease (24%), only behind the Mets (30%). Those two players were the only free agents that the North Siders were listed inside the top-3.
However, if the Cubs came out of the offseason with both Bregman and Cease, Cubs fans would be more than fine with that. Both players would elevate this Chicago team and put this group into World Series contention.
The Cubs were in on Bregman last offseason, but the 31-year-old ultimately signed a multi-year deal with the Red Sox. With Bregman opting out of that current deal, though, Chicago could pursue him once again this winter.
Bregman’s bat would be a huge upgrade for the Cubs after he hit .273 with 18 home runs, 28 doubles, and 62 RBI across 114 games in 2025. The 10-year veteran would fit perfectly in that third base/designated hitter role for the coming years.
The major concern is whether the Cubs want to replace Matt Shaw with Bregman at third base. Both players play the same position, and Bregman might not want to sign with the Chicago if he is only going to DH.
If you are the Cubs, how do you take away Shaw’s glove in the field? He was a finalist for the Gold Glove Award as a rookie and should be a better all-around player heading into his second year in 2026.
As for Cease, he makes more sense as a target for the Cubs, which explains why he received 24% of the votes to land with them. Chicago could use a top-of-the-line starting pitcher, with Shota Imanaga’s future up in the air and Justin Steele still working his way back from elbow surgery.
Cease is coming off a down year in which he finished with a 4.55 ERA, but the metrics suggest that he got a bit unlucky on the mound in 2025. His expected ERA (3.43 ERA) was 112 points lower than his actual ERA, and his whiff rate (33.4%) and strikeout rate (29.8%) both ranked in the top 11% of the league.
So, signing both Bregman and Cease could help push this Cubs team over the top.