Report: Cubs Met with Alonso at Winter Meetings
While the Winter Meetings aren’t technically over quite yet, most teams and front offices are currently on the way back home. That hasn’t stopped more news from coming out, with Jon Heyman of USA Today reporting that the Chicago Cubs held a meeting with Pete Alonso on Tuesday at the Winter Meetings.
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
Alonso signed a five-year deal with the Baltimore Orioles on Wednesday afternoon, a contract that cost Mike Elias $155 million. The Mets lost their star first baseman, with the Orioles gaining one of the best power hitters in baseball. I already discussed the deal’s implications for the Cubs, but this new report adds some interesting twists.
Alonso would most likely have been used in the designated hitter role with the Cubs unless a trade involving Michael Busch came out of nowhere, which does not seem likely. The Cubs’ offer for Alonso, if they made one, has yet to be reported. Although they clearly cannot still pursue Alonso, it could be telling for their future offseason plans, including the pursuit of top free agent Alex Bregman, who will also be quite costly in terms of total contract value.
