Oh don’t lie, you guys love this offseason shit. The Athletic’s Jim Bowden released his annual list of the top-50 free agents, ranked them, connected them to the best potential fits this offseason and he also provided contract predictions for all 50 players. As we’ll discuss later on, some of those projections seem a bit off and as much as I’d love to see the Chicago Cubs target most of the free agents that Bowden believes could be fits at Wrigley Field, there are a handful that don’t necessarily feel realistic.
I’m also looking at this list through the mindset of Jed Hoyer, his front office and how ownership has operated under the Ricketts. I do expect the Cubs to go out and land a few impact free agents, but I’d be lying if I truly felt they’ll be players at the very top of the market.
So, let’s rank the 10 free agents Bowden has linked to the Cubs in his top-50 list in order from most likely to least likely to be signed by Hoyer based on the Cubs’ previous activity in free agency.
One quick note before we get into the Cubs-related free agents, Bowden lists Kyle Tucker as the No. 1 free agent in this class, but he does not mention the Cubs as one of the best team fits. Instead, Bowden names the Los Angeles Dodgers, New York Yankees, New York Mets, Philadelphia Phillies and San Francisco Giants as the best fits for Tucker, while predicting the 28-year-old All-Star outfielder will get a 10-year, $427 million contract.
All right, now to the 10 free agents who Bowden links to the Cubs as being one of the best team fits.
1. Brad Keller – contract prediction 2 years, $15 million
The 30-year-old pitcher completely changed the trajectory of his career with the Cubs in 2025, and if Bowden’s prediction of a two-year, $15 million deal is what Brad Keller ends up signing in free agency, then I expect Hoyer to be all over this. Keller was forced to sign a minor league deal after his atrocious performance in 2024, and for the first time in his pro career the right-hander worked as a full-time reliever with a new and improved fastball/slider combo.
Age isn’t a concern here and while injuries can pop up at any time Keller is now a few years removed from surgery and didn’t show any signs of decline as the 2025 season progressed. If his market remains in the two-year range, then the Cubs will certainly be in the mix after his results with the team this past year.
Keller ranked No. 34 in Bowden’s top-50 list.
Other teams mentioned: Dodgers, Mets, Braves, Phillies, Cardinals, Tigers, Astros
2. Drew Pomeranz – contract prediction 1 year, $5 million
Remember, I’m ranking these as who I think is most likely to be signed by the Cubs, not their actual ranking as players in free agency. Anyway, similar Brad Keller, veteran lefty Drew Pomeranz was a hidden gem for the Cubs’ bullpen as the 36-year-old was acquired in a minor trade with the Seattle Mariners at the end of April. Pomeranz, who had not pitched in MLB since 2021, finished the 2025 season with a 2.17 ERA and 28.1 K% in 49.2 innings.
Given his age, Pomeranz isn’t likely to command a multi-year contract, so if the Cubs believe he can come close to repeating his results in 2026, they’ll likely remain in contact with the left-hander this offseason.
Other team mentioned: Padres
3. Dylan Cease – contract prediction 6 years, $187 million
All right, maybe I’ll look like a fool believing that the Cubs will be a serious suitor for Dylan Cease, but I think the interest is real. Out of all the starting pitchers on this list I do think Cease is the most realistic target for the Cubs this offseason. However, I do have to qualify this by saying I don’t think the Cubs nor any other team will offer Cease a six-year deal.
Again, maybe I’ll be completely wrong about that and Scott Boras gets a team to bite. But there’s just way too much inconsistency with Cease and he’s coming off a rough season. However, he’s still uber talented and has shown the ability to be an elite starting pitcher.
If Cease overestimates his market and remains unsigned come January, then at that point I’d give the Cubs a decent shot at swooping in and getting the right-hander to sign a shorter contract with opt outs.
Other teams mentioned: Padres, Braves, Mets, Orioles, Giants, Angels, Red Sox, Tigers
4. Michael King – contract prediction 3 years, $75 million
Maybe the Cubs can sneak in here and get lucky because Michael King has been great when healthy, but the problem is the 30-year-old wasn’t healthy in 2025 and he only has one full season of success as a starting pitcher. Still, King has ace potential as he showed in 2024, when he had a 2.95 ERA in 173.2 innings.
The right-hander has made 161 career appearances in the majors, which includes 64 starts. In those 64 games King has a combined 3.35 ERA with a 26.4 K%. However, he only threw 73.1 innings in 2025 with the San Diego Padres, missing half the year because of a a pinched thoracic nerve and tossed a total of 17.2 innings to end the season when he returned in August.
However, the risk/reward behind signing King is that if he is back to 100% health, then the Cubs could get a top of rotation arm that they need in 2026. If King’s market stays in that three-year range, then I could definitely see the Cubs taking on the risk.
Other teams mentioned: Padres, Yankees, Orioles, Braves, Mets, Angels, Astros, Tigers, Red Sox
5. Zac Gallen – contract prediction 5 years, $135 million
Just like Cease, I think Zac Gallen will be a target for the Cubs this offseason, but there’s no chance in hell they’ll come close to offering him that much money. I don’t think any other team will either.
The Cubs were reportedly interested in trading for Gallen during the 2025 season, but the Arizona Diamondbacks held on to him. Gallen, who had been a Cy Young contender in years past, finished this past year with a 4.83 ERA in 192 innings. He made 33 starts and the concerning part was that this was his second year in which Gallen’s numbers declined across the board.
From 2019-2023, Gallen maintained a strikeout rate between 26 and 29 percent. At his best, Gallen was limiting walks to 2/9IP, but in 2024 his strikeout rate dipped a little, down to 25.1%, still good, but in 2025 it was only at 21.5%, while the walks increased to above three per nine innings pitched.
The bright spot to Gallen’s 2025 season is that in his final 11 starts he recorded a 3.32 ERA in 65 innings and posted eight quality starts. Yet, the strikeout rate was hovering in the 20% range, so that’s not exactly what you want if you’re predicting future success.
So, why would the Cubs even be interested? Again, it’s about value, containing the risk, and I don’t think Gallen’s market is going to be crazy. A one-year or two-year deal to prop up his value again? Yeah, that’s more in the realm of possibility than Gallen getting $135 million guaranteed after his showing in 2025.
Other teams mentioned: Orioles, Red Sox, Tigers, Astros, Padres, Giants, Braves, Mets, Cardinals
Not Buying It
Here are five more free agents that Bowden linked to the Cubs and I’m not buying the connection.
Framber Valdez – contract prediction 6 years, $190 million
Bo Bichette – contract prediction 7 years, $189 million
Alex Bregman – contract prediction 6 years, $182 million
Ranger Suárez – contract prediction 6 years, $164 million
Tatsuya Imai – contract prediction 7 years, $154 million
Not saying the Cubs shouldn’t go after these guys, but I don’t buy that Hoyer will commit that kind of money to these specific free agents. Especially the starting pitchers. Since becoming the top boss in the front office, Hoyer’s largest free agent contract to a starting pitcher has been four years, $68 million to Jameson Marcus Stroman agreed to a three-year, $73 million deal, but he opted out after year two.
Meanwhile, Shōta Imanaga agreed to a four-year, $53 million contract that includes both player and team options. There’s still a giant question mark surrounding Imanaga heading into the offseason and there’s a small possibility that he enters free agency.
So yeah, I don’t think the Cubs will be in on any of the starters that will command long-term contracts with an AAV in the $30 million range. Right or wrong, the Cubs under Hoyer haven’t operated in those waters.
As for Bo Bichette, sure he’d be welcomed, but he had a great bounce back season in 2025, and I’d bet a few teams will be lined up to pay him as a shortstop this winter. The Cubs have Dansby Swanson and while Bichette could transition to second or third base, he’s still going to get shortstop money, which I find something the Cubs won’t want to do.
Alex Bregman? Cubs already tried last year and he passed on them. Now, he’s a year older and I doubt the Cubs will all of a sudden cave and offer the 32-year-old a longer contract.
