5. Los Angeles Dodgers
Michael Conforto
I was tempted to put Max Muncy here, given the uncertainty surrounding his $10 million club option for 2026. But he’s been so good when healthy this season, and recent reports suggest that L.A. is actually leaning towards picking that option up.
Which brings us to Conforto, who won’t be back with the Dodgers next year even if fans have to personally remove him from Chavez Ravine. Things have been that bad for what seemed like one of the more underrated signings of the 2024-25 season. Conforto felt ticketed for a big bounce-back year, but it simply hasn’t materialized. He’d be moving on at the end of the year even if the Dodgers didn’t have eyes on another corner outfielder in Kyle Tucker.
-Landers
4. Chicago Cubs
Kyle Tucker
Nobody in Wrigleyville seriously believes that Tom Ricketts is willing to go to unprecedented lengths to make Kyle Tucker a Cub for life. This is a franchise that failed to even re-invest the savings from the Cody Bellinger salary dump at the deadline, so there’s little hope they’re ready to offer a deal that would more than double the largest contract in franchise history.
That’s right. Tucker is expected to command $400 million, even with his second-half slump factored in, and the Cubs are yet to crack the $200 million mark for a player, despite being one of the most valuable organizations in the league. When he’s been at 100 percent, the four-time All-Star has done exactly what Jed Hoyer hoped he’d do: lengthen the lineup and make everyone around him better.
But in typical Cubs fashion, they’re keeping one foot on each side of the line: making an all-in, win-now move in acquiring Tucker, then playing it safe in virtually every other move they made to put a contender around him.
-Jake Misener, Cubbies Crib
3. Toronto Blue Jays
Chris Bassitt
Call me crazy, but I actually do think that Bo Bichette winds up staying in Toronto. He’s a weird profile given his defensive struggles (and the fact that he really should at least slide over to third base in the near future), and he’s more valuable to the Jays than just about anybody else.
Bassitt, though, is a different story: The Jays still have one more year of Kevin Gausman as well as Jose Berrios and a potential option on Shane Bieber that seems likely to be exercised. That’s the foundation for a solid rotation before we even get to uber-prospect Trey Yesavage’s pending arrival. The guess here is that Toronto will let somebody else pay Bassitt, who richly deserves another nice payday based on his yeoman’s work over the last few years, and look to add depth for cheaper.
-Landers
2. Philadelphia Phillies
Ranger Suarez
The Philadelphia Phillies have two major free agents to worry about with both Kyle Schwarber and Ranger Suarez set to hit the open market this winter. Keeping both would be the dream scenario, but I’m not sold that’ll happen with how much money Philadelphia has already committed to its roster and how much it’ll cost to retain both. I believe the Phillies will and should re-sign Schwarber and let Suarez walk.
It might be controversial to prioritize a 32-year-old DH over a 29-year-old starting pitcher, but this comes down to need. The Phillies can be offensively challenged at times even with Schwarber having an MVP-caliber year. It’s hard to envision this team being good enough offensively without Schwarber to win a World Series.
Suarez, on the other hand, is far easier for the Phillies to replace. Even without him, they’ve got Zack Wheeler, Christopher Sanchez, Aaron Nola, Jesus Luzardo, and even Andrew Painter knocking on the door. The Phillies are flush with starting pitchers, and don’t need to bring back Suarez in the same way they need to re-sign Schwarber. Suarez is going to sign a lucrative deal elsewhere and likely thrive.
-Rotman
1. Milwaukee Brewers
Brandon Woodruff
This one is going to hurt Brewers fans. Brandon Woodruff, the longest tenured Brewer, faces a tough decision this offseason; on his current contract, there exists a $20 million mutual option. Mutual options are hardly ever picked up as both the team and the player have to agree on their value and believe that accepting the option is the best-case scenario for both parties. What’s interesting about Woody’s situation is that he holds a sizable $10 million buyout if the Brewers don’t pick up the option, meaning Milwaukee is going to spend $10 million whether they retain Woody on their 2026 roster or not.
While there’s a small chance that Woody and the Brewers come to an agreement on the mutual option, more likely Woodruff will decline his end of the deal and search for a multi-year contract. In such a scenario, it will be difficult for the small-market Brewers to match the offers of their counterparts with larger payrolls. Woody’s ties to the Brewers’ organization could help the team's chances of retaining their fan favorite starting pitcher, but such a contract won’t come cheap.
-Owen Jonas, Reviewing the Brew