Joe Ryan and other trade targets the Cubs could land at the Winter Meetings

Besides signing reliever Phil Maton to a two-year deal in November, the Chicago Cubs have been their usual quiet selves in the beginning stages of the offseason.

Of course, that should change at the Winter Meetings, which was the site of the Cubs' big swing last winter. Technically acquired the day after the annual event ended in 2024, Kyle Tucker was brought in to shake things up in the middle of the North Siders' order.

With Tucker now set to depart in free agency, the Cubs are once again looking for a means to improving their team to compete for their first division title since 2020. It wouldn't be surprising to see the team make another big trade at or around the Winter Meetings, and if they do so, these are the top players they may go big-game hunting for.

3 stars Cubs can make blockbuster trade for at Winter Meetings

Joe Ryan

One of the most prominent names on the pitching market, Ryan has been a rumored Cubs target dating back to the trade deadline.

Armed with one of the most run-heavy fastballs in the game, Ryan has become a dependable force in recent years, authoring an ERA below 3.60 in three of the past four seasons. He's also proven durable, making at least 23 starts in every season since 2022.

With two years of team control remaining via arbitration, the 29-year-old would cost an arm and a leg in a trade. But if the Cubs are serious about pulling off another Winter Meetings blockbuster and acquiring a true frontline starter for the rotation, Ryan should be their top target.

MacKenzie Gore

Another arm the Cubs were attached to at the trade deadline, Gore stumbled in the second half of the 2025 season, which could lower his price tag down to a more tolerable ranger for Jed Hoyer and company.

After securing an All-Star bid thanks to a 3.02 first-half ERA, Gore struggled badly down the stretch, surrendering a 6.75 ERA and .370 wOBA to opposing hitters as the Midsummer Classic. A lot of that had to do with an injury to his throwing shoulder, which could prove to be problematic if not fully recovered.

Still, at just 26 years old, Gore lived in the 80th percentile in both strikeout and whiff rate this past season. Sometimes, you just need to bet big on raw talent, and the Nationals' southpaw has that in spades.

Wilyer Abreu

On the surface, this is an odd one. The Cubs already have plenty of outfield depth, even sans Kyle Tucker. Seiya Suzuki or Owen Caissie is likely to take over the right field role in his absence, and Kevin Alcantara profiles as a versatile outfielder who could handle the corners with ease.

Likewise, the Cubs don't really have the expendable pitching the Red Sox will be looking for in a trade for one of their many outfielders. So, how exactly does Abreu profile as a Cubs trade target?

Well, Abreu is a sterling defender in right field, having just won a second straight Gold Glove at the position in the American League. He, Ian Happ, and Pete Crow-Armstrong could form one of the greatest defensive outfields in baseball history.

Likewise, he provides power from the left-handed site of the plate — he hit 22 home runs in just 115 games in 2025. If the Red Sox are satisfied with their addition of Sonny Gray, they could look to the Cubs' prospect coffers (or perhaps Matt Shaw at third base) as means for receiving fair value in an Abreu trade.