
With Kazuma Okamoto officially heading to Toronto on a four-year, $60 million deal, another potential free-agent target is off the board for the Chicago Cubs. That signing tightens the infield market, and for a Cubs team that’s been relatively quiet this offseason, it raises more questions than answers. While the bullpen has been the primary focus-understandably so after losing nearly every key contributor outside of Daniel Palencia-the infield remains a puzzle with few clear pieces in place.
Unless something changes dramatically, it looks like the front office is banking on internal growth from young hitters like Owen Caissie and Moises Ballesteros. Both have exciting upside, but relying on unproven talent to fill major roles is a gamble-especially for a team trying to stay competitive in a wide-open NL Central.
Still, the offseason isn’t over, and two of the biggest names on the market-Alex Bregman and Bo Bichette-remain unsigned. Let’s take a closer look at how (or if) either could fit into the Cubs’ plans.

Alex Bregman: Cubs interest seems more smoke than fire
There’s been no shortage of Alex Bregman rumors this winter, and the Cubs have popped up here and there as a team with potential interest. But the buzz around Chicago has been more background noise than serious momentum. While Bregman would certainly bring a veteran presence and a proven bat to the hot corner, the Cubs don’t appear to be in the thick of the bidding war.
Toronto was once seen as a major player for Bregman, but with Okamoto now in the fold, that door seems closed. That leaves the Arizona Diamondbacks and Boston Red Sox as the two most prominent suitors still in the mix. MLB.com’s Mark Feinsand recently pointed to both clubs as serious contenders, with reports suggesting Boston has made an aggressive push to land the three-time All-Star.
As for the Cubs, this has the feel of a team doing its homework-checking in, staying informed, but not necessarily preparing to make a serious offer. Unless Bregman’s market unexpectedly collapses, it’s hard to envision him anchoring third base at Wrigley Field in 2026. For now, it looks like Chicago is content to monitor from the sidelines.
Bo Bichette: A more complicated-but intriguing-possibility
Now here’s where things get more interesting. The Cubs have reportedly joined a growing list of teams eyeing Bo Bichette, the 27-year-old shortstop who’s become one of the most dynamic infielders in the game. The Yankees, Dodgers, Red Sox, Blue Jays, and Phillies are all reportedly in the mix as well, which speaks to just how coveted Bichette is this winter.
For the Cubs, though, a move for Bichette wouldn’t be simple. The only plausible path would involve parting ways with Nico Hoerner-one of the team’s most reliable and defensively gifted players.
Hoerner, a Gold Glove winner and clubhouse leader, is a cornerstone of the current roster. Trading him would be a seismic shift, and not one the fanbase would embrace easily.
That said, if the front office believes a long-term extension with Hoerner isn’t likely, this could be the moment to explore a bold pivot. Swapping Hoerner for a top-tier arm and bringing in Bichette as a long-term solution up the middle would be a high-risk, high-reward play. It’s a lot of moving parts, and nothing suggests this is imminent-but it’s not out of the realm of possibility.
Where do the Cubs go from here?
Chicago’s offseason has been more about restraint than splash, and that’s left fans wondering what the bigger plan is. With the bullpen getting a much-needed overhaul, the next step has to be addressing the lineup-either by doubling down on youth or making a major move in free agency or via trade.
Bregman feels like a long shot, and Bichette would require a significant shake-up to the current roster. But with Opening Day still months away, there’s time for the Cubs to make their move. Whether they choose to go big or stay the course, the pressure is on Jed Hoyer and the front office to define the direction of this team-and soon.