The Cleveland Guardians can go in many directions during MLB's Winter Meetings.
MLB’s highly anticipated Winter Meetings begin in Orlando on Sunday, starting what is typically some of the most active days of trades, free agent signings, and other transactions of the offseason.
Before all of the action really gets started, here are three bold predictions about what could happen over the next week or so as it pertains to the Cleveland Guardians.
Steven Kwan Trade Rumors Continue, But No Deal Gets Done
It’s understandable why so many contenders want to trade for Steven Kwan. He’s one of the best leadoff hitters in the sport, while also being one of the top defenders, too.
However, the Guardians don’t need to trade him during the Winter Meetings. They don’t need to trade him this offseason. Cleveland doesn’t need to trade him at all.
Because Kwan still has two seasons of team control left, and the Guardians need more help on offense as is, it makes the most sense for the Guardians to dangle his name in trade discussions with multiple teams, get an idea on what type of package he could return, then re-group and revisit a trade later this offseason or leading up to the deadline.
Oct 2, 2025; Cleveland, Ohio, USA; Cleveland Guardians outfielder Steven Kwan (38) breaks his bat on a ground out in the third inning against the Detroit Tigers during game three of the Wildcard round for the 2025 MLB playoffs at Progressive Field. Mandatory Credit: Ken Blaze-Imagn ImagesGuardians Sign A Veteran Outfielder
Cleveland’s front office has a history of being active at the Winter Meetings. Last year, it was the mega Andres Gimenez trade, and back in 2022, the Guardians signed one of the best free-agent power hitters on the market in Josh Bell.
That said, it makes sense for Cleveland to make some sort of move to improve the offense while they’re in Orlando.
The move that makes the most sense is to sign one of the veteran free-agent outfielders currently on the market. Mike Yastrzemski, Adolis Garcia, Harrison Bader, and Austin Hays are all remaining unsigned and would make a lot of sense for Cleveland.
Guardians Trade A Starting Pitcher
The price for pitching is always high, and it looks like that’s the same reality for the 2025 offseason. The Washington Nationals were able to trade a reliever with a 4.48 ERA for one of the top catching Prospects in baseball from the Seattle Mariners.
With the Guardians actually being in a good spot in terms of starting pitching depth, it would make sense for them to trade an arm for help in the big-league lineup. Could Logan Allen, Joey Cantillo, or Doug Nikhazy be a part of a different uniform by the end of the week?