Add Two More Top Free Agents the Cubs Almost Maybe Signed?

All right, these type of rumors and reports are either taken as a data point that could lead to further speculation on what a team’s plan might be or fans will immediately shut it down and decry them as an attempt of said team trying to appease the fan base by showing that they tried. I probably fall somewhere in the middle here because I do think it is somewhat intriguing that the Chicago Cubs reportedly met with Pete Alonso right before he signed a $155 million contract with the Baltimore Orioles.

The Cubs left the Winter Meetings in Orlando, Fla., without signing a major free agent, but we got a few more “they tried” reports on two significant free agents. The latest comes from national MLB insider Jon Heyman, who reported on Wednesday night that the Cubs along with the Boston Red Sox met with Alonso in person on Tuesday night.

Does this supposed meeting between the Cubs and Alonso matter now that he’s agreed to a five-year deal with the Orioles? Not necessarily, but it furthers the narrative around the Cubs looking to add an impact bat this offseason with Kyle Tucker expected to go elsewhere.

The Red Sox and Cubs were the other teams that met with Pete Alonso in Orlando Tuesday night. He was never spotted by media as he went through a side entrance and used a service elevator.

— Jon Heyman (@JonHeyman) December 10, 2025

That one wasn’t really a true pat on the back type of report because it’s not like Heyman even relayed any offers from either the Cubs or Red Sox for Alonso. So, big picture, the Cubs met with Alonso at the Winter Meetings and this week Robert Murray also reported that the team had a meeting over Zoom a few weeks ago with Alex Bregman.

Something to keep an eye on. I don’t see the Cubs suddenly opening up the checkbook for multiple top free agents, but if they’re kicking the tires on some bats, then I’m thinking they’re working hard on a trade for a starting pitcher. Again, I doubt the Cubs sign both a guy like Tatsuya Imai or Michael King AND Bregman. But a trade for MacKenzie Gore/Edward Cabrera and then bringing in Bregman? Yeah, maybe.

Here’s the other “they tried” report and this one stings a little more. According to Bruce Levine, free agent closer Devin Williams preferred to sign with the Cubs this offseason and although the Cubs had a three-year offer on the table for him, the money didn’t come close to the $51 million that Williams received from the New York Mets.

The Cubs met with Pete Alonso before he signed with the Orioles.

Also, Devin Williams' preference, all things equal, was to sign with the Cubs over the Mets, sources told @MLBBruceLevine, but the Cubs' offer didn't get to the $51 million that Williams got. pic.twitter.com/oC4au5hJxx

— 670 The Score (@670TheScore) December 10, 2025

Hey, sometimes this can be a blessing in disguise. I mean, just last offseason the Cubs finished second to the Los Angeles Dodgers for Tanner Scott. The left-handed closer had a terrible 2025 season in LA, ending the year with a 4.74 ERA, 10 blown saves, and two stints on the injured list which included Scott missing the postseason.

So, who knows, not every free agent signing works out, but obviously you want your team signing stars.

Since the start of the offseason the Cubs have now reportedly been in the mix for Dylan Cease, Emilio Pagan, Pete Alonso and Devin Williams, all who signed somewhere else.