2025 Winter Meetings Recap: Cubs Lay Offseason Groundwork, Bregman Still a Strong Possibility, Tony Vitello Interview
No one can predict how baseball’s offseason is going to come together, unless you’re Biff Tannen with the Grays Sports Almanac Back to the Future II. The Winter Meetings Preview was full of optimism and hope of an eventful few days ahead, but quite the opposite happened.
The meetings were still interesting, but several teams, including the Cubs, didn’t end up finalizing any large transactions. Kyle Schwarber, Edwin Díaz, and Pete Alonso were the trio of stars to ink contracts during the three-day conference. Kyle Finnegan, Gregory Soto, and Michael Soroka each found new homes as well, though their deals paled in comparison to the previous three.
The Winter Meetings used to be seen as the main event, a place where the offseason hot stove is guaranteed to heat up and provide several blockbuster moves. But this year, like many others in recent memory, the baseball world was left grasping for straws until Schwarber signed on Tuesday morning. The same rumors were being regurgitated by all members of the media as everyone was desperate for new information to share and discuss.
The Cubs didn’t make any major-league moves, but a lot of discussions took place behind the scenes. Teams laid the groundwork for what could be a busy two weeks before Christmas. The front office met with Alonso before he became an Oriole, which took a lot of people by surprise. Alonso had received overtures from the Cubs in past years through free agency and the trade market, but Michael Busch‘s breakout eliminated that fit.
The consideration of spending on Alonso should give more optimism in terms of the pursuit of Alex Bregman, whom the team met with over Zoom in recent weeks. Bregman’s name was mentioned constantly throughout the Winter Meetings, with the Cubs and Red Sox being two teams heavily linked to the superstar.
Bregman missed a large chunk of games in 2025 due to a soft tissue injury, which should cause some concern when projecting him in a lineup for the next several years. Despite that and his decreased production from his last five years to his first five, the Cubs clearly think he will age well. The Scott Boras client, who will turn shortly after Opening Day, stands out as the main offensive target on the free agent market. His excellent plate discipline skills would drastically improve an already promising Cubs lineup for the 2026 campaign and beyond.
Tatsuya Imai and Michael King are two of the best free agent pitchers looking for teams, with the Cubs being heavily connected to both of them. As seems to be the case rather often, finances could very well prevent either of them from landing on the Northside this winter.
Speaking of finances, the Cubs have already allocated just over $10 million to the bullpen, signing both Phil Maton and Hoby Milner. Jed Hoyer and Carter Hawkins did an impressive job of constructing their bullpen last year, with additions such as Brad Keller and Drew Pomeranz providing more than anyone could have expected. Several arms that finished the year with the Cubs are now gone, with Soroka and Andrew Kittredge already joining new — or old — teams.
Keller and the Cubs have mutual interest in a reunion, but finances could get in the way since Keller is one of the most sought-after bullpen arms on the market. Pete Fairbanks and Luke Weaver are two other plausible additions who could give the team a hard-throwing righty for late in games. Fairbanks has worked with Tread Athletics in the past, giving him a connection to Tyler Zombro, who has continued to build the pipeline between Tread and the Cubs.
Utilizing the trade market is something Hoyer and his front office do often. Following the 2023 offseason, the team traded for Busch. Last winter, Kyle Tucker arrived in a deal with the Houston Astros. Negotiating another deal of sizable magnitude seems to be in the cards this winter, with starting pitching likely the focus.
Edward Cabrera and MacKenzie Gore came up frequently in Orlando, with Cabrera the most viable in terms of prospect cost. Reports have indicated that the Orioles are extremely interested in his services as well, which could put the Cubs in a bidding war for the 27-year-old. He has some injury risk, but has been a target of the team for several months now.
In all honesty, the Winter Meetings just aren’t the same as they used to be. To use teenage slang and lingo, it’s fair to say that they’re “washed.” What was once a cornerstone of the offseason has become an excuse for people throughout baseball to hang out and socialize.
With the milestone summit of the offseason behind us, now comes the time for all those conversations to start yielding a little more action.
Even if the transactions were sluggish, one of the best parts of the Winter Meetings is how many of baseball’s important figures are in the same building. Reporters and team officials alike are meeting up with friends and are often available to have conversations in the hotel hallways. One of those individuals was Tony Vitello, who recently left the University of Tennessee to serve as manager of the Giants.
After leading the Volunteers to a College Baseball World Series title in 2024 as the pinnacle of his eight seasons in Knoxville, Vitello became the first college coach to move to MLB without having coached in professional baseball. He took a moment to speak with Cubs Insider in Orlando about his unique perspective on the Cape Cod Baseball League, as well as the life change he’s taking on.
“I think the development is huge, but also there’s a scouting aspect to it,” Vitello said. “When you get into the potential of being a Major League draft pick, it’s a big decision for a team to take somebody and invest in them, and they want to know exactly what they’re getting. In scouting, unfortunately, you’re trying to predict the future, so there’s no way of exactly knowing that [outcome].
“The better the competition and the better the setting, the more likely you are to make good decisions. Cape Cod provides a good stage for knowing what the best competition looks like and what the best scenery for potential Major League draft picks looks like.”
The Cubs love drafting players who spent time on Cape Cod, with the scouting department seeing that time as extremely valuable and telling of who they can become on a major league roster.
“I think one thing is that working with young guys is an important part of our deal,” Vitello continued. “In order to coach guys at the big league level, they have to first get there. There are minor league guys, or there are young prospects that are trying to stay there. Ultimately, those young guys are trying to have success, too.
“I feel like there are some similarities in coaching there. Once you get to guys that are established big leaguers, or you’re talking about a 35-year-old veteran, those are different conversations. I think there’s a lot to learn, but there’s fortunately some things to fall back on, as well, that I think will help.”
While the Giants may not be heading into a rebuild, they have a young core that will need mentorship, which is why Vitello’s experience will be vital to their future success.
