Back on October 2, I went through the laundry list of impending Chicago Cubs free agents. Between the guys with club options (3), player options (1), mutual options (4), and unrestricted free agents (10), the Cubs have a TON of openings coming up this winter. And although “this winter” will be broken up by a lockout as the new CBA is negotiated, eventually players will sign with new teams, and there will be baseball again. So while we wait for the postseason to wrap up, I thought we could take an early look at some of the best free agent fits for the Chicago Cubs this offseason.
Unlike some of our prior dives into this topic, today I will not consider the projected contract/cost of any given free agent as a limiting factor in determining the best fit(s). Obviously, that will matter (perhaps especially in a new era of CBA payroll rules or salary caps/floors), but the Cubs have a ton of money coming off the books and a solid enough core to justify literally any acquisition.
Cubs Free Agents — Players to Target This Winter
1. Tarik Skubal, SP (LHP)
You should already know who Tarik Skubal is, but in case you’ve lived under a rock the last few years, let’s just put it this way: Until Jacob Misiorowski exploded onto the scene this season, there was no argument regarding the top arm in MLB (incidentally, these two matched up in Game 1 of the NLCS last night). Indeed, Skubal won the AL Cy Young award in both 2024 and 2025. And probably could’ve been a top candidate this year if it weren’t for the injury (hold that thought) and mid-season trade to the NL.
To that end, yes, Skubal’s 2026 campaign included an injury and surgery that limited him mid-season. But it was still plenty productive overall: 26 starts, 158.2 IP, 2.72 ERA, 2.51 FIP. Notably, and perhaps most importantly, his average fastball velocity from August on was 97.0 mph (identical to 2024, and less than a full click behind 2025).
Also notable? Skubal is still just 29 years old, and won’t turn 30 until a week before Thanksgiving. So he’s pretty young.
Why does he fit the Cubs? Well, aside from the fact that he fits every single team in baseball because he’s the best pitcher in baseball, the Cubs have an acute need for starting pitching next season.
Gone from the team the day after the 2026 World Series: Kevin Gausman, Shota Imanaga, Matthew Boyd, Clay Holmes, and David Peterson.
Colin Rea might also be an option casualty, and we have next to no idea what to expect from Ben Brown (will he start? will he relieve? will the neck injury ever go away?), Justin Steele (can he be anywhere close to the same level of effectiveness after TWO lost seasons?), Edward Cabrera (can he stay healthy? is he good enough even when he is healthy?), and Cade Horton (will he even appear next season?).
But there’s more. The Cubs, under Jed Hoyer, tend to favor left-handed starting pitchers. I’m not entirely sure what the reason for that is, but we’ve been noting it for years. We suspect it has something to do with the conditions at Wrigley Field (sight lines, stadium quirks, wind, whatever). And Skubal is a lefty.
Likewise, it’s not just that Tarik Skubal is a dominant starter; he’s a dominant starter who succeeds specifically on velocity and strikeouts — the very thing this team is perpetually chasing and clearly incapable of developing internally.
Bottom line: a lefty starter who throws hard, strikes people out, is on the right side of 30, and is as dominant as anyone out there is as platonically ideal of a fit as any free agent could possibly be for the 2027 Chicago Cubs season.
Everyone will want Tarik Skubal, and outbidding the Mets/Dodgers/whomever will be borderline impossible, but he is without a doubt the No. 1 Cubs free agent target this winter. His friendship with Alex Bregman is a nice boost. Perhaps Bregman can do some lobbying this winter.
But make no mistake: Short of some serious CBA payroll restrictions, Tarik Skubal is about to get the richest free agent pitching contract in MLB history. Well north of $300 million, and perhaps substantially so. The Cubs, meanwhile, have never given out a deal worth more than $184 million, and I doubt sincerely that their first would be to a pitcher.
But Jed Hoyer seemed to soberly acknowledge his team’s shortcomings in this department at his year-end presser. So maybe something will finally change.
Los Angeles Dodgers starting pitcher Tarik Skubal | Kamil Krzaczynski-Imagn Images1B. Kaima Taira, SP (RHP)
This offseason, 26-year-old Japanese right-hander Kaima Taira is going to be posted and made available to all 30 teams in MLB. Brett wrote all about him earlier today, making him sure SEEM like an excellent target for the Cubs this offseason (throws hard, strikes guys out, is just generally awesome). His short and stout stature (5’8″, 220 lbs) might create some concern, but … the guy posted a 1.36 ERA over 146.0 innings this season, while touching 100 mph, so … maybe don’t worry about that.
Because I don’t have much first-hand information on him (I’ve never personally watched him play), it’s tough for me to rank him. But by some accounts (including Jeff Passan), he’s the next best starter available this offseason after Tarik Skubal. Combine that with his age and velo, and it’s tough not to want to rank him right here behind Skubal for the Cubs.
For now, though, I’m just giving him the “1B” treatment. You can and should read much more about Taira from Brett.
2. Adrian Morejon, RP (LHP)
The Cubs have notable vacancies in the outfield and the rotation, but they simply cannot afford to have a bullpen as bad as this season again (-0.6 fWAR, 3rd worst in MLB). Once Jacob Webb wore down from overuse around mid-August, the team had exactly no dependable relievers down the stretch, and it cost them dearly.
Now, I do think the team is in a better position heading into 2027 than they were heading into 2026. Daniel Palencia, Ryan Zeferjahn, Ryan Rolison, and a potentially healed Phil Maton provide a much better floor with more upside than they had coming into this year, but they clearly need to raise the ceiling with some high-level talent and velocity. And for my money, there’s no better option than Adrian Morejon.
The 27-year-old left-handed set-up man to Mason Miller is hitting free agency at an incredible time. His 2026 season marked three straight fantastic campaigns and included a significant leap in velocity, too:
2024: 2.83 ERA, 26.1 K%, 97.0 mph 2025: 2.08 ERA, 24.5 K%, 96.6 mph 2026: 2.83 ERA, 30.4 K%, 99.1 mphMorejon also had 3 saves and 28 holds this past year. He’s as good as it gets, and Mason Miller is the only reason he wasn’t the Padres closer.
In a lot of ways, his fit mirrors Tarik Skubal: He’s the right age, he’s left-handed, he throws hard, he strikes people out, and he fills the next biggest hole on the Cubs (impact relief pitching).
The Cubs have also changed their approach to relievers these past couple of offseasons. Two winters ago, the Cubs tried to sign Tanner Scott to a big free agent deal well outside of their usual range. And last offseason, the Cubs signed multiple free agent relievers, including some to multi-year deals. If the trend holds, and the Cubs are actually serious about improving the quality and ceiling of the stuff in this organization, they’ll hand Adrian Morejon the richest free agent relief contract in franchise history this winter.
But once again, be warned: Morejon will be highly sought-after and handsomely paid. And although he has a history with Cubs bench coach Ryan Flaherty, that was years ago … and I wouldn’t be surprised if Flaherty becomes a managerial candidate sometime soon.
San Diego Padres relief pitcher Adrian Morejon (50) | David Frerker-Imagn Images3. Seiya Suzuki, OF (RHH)
I was conflicted on which of the two big free agent outfielders on this list to rank first, but ultimately, I’m going with the devil I know, Seiya Suzuki.
Suzuki is coming off the best overall season of his five-year big league career, finishing with 26 HRs (2nd most of his career), a 0.52 BB/K (best), 134 wRC+ (2nd best), and 4.6 fWAR (best). His defense in right field was also notably stronger this season, which feels critical for a Cubs front office that clearly values defense more than most.
Suzuki did have another one of his streaky offensive seasons, but as always, he recovered and finished strong. Suzuki’s age doesn’t help (next year will be his age-32 season), and he has surely played himself into an even richer contract than the one he just wrapped up with the Cubs. But I don’t think the team can afford to lose his bat without replacing it this offseason. And if that replacement is going to come via free agency, there is no better bet available on the market.
I also think the Cubs will not want to go long without a Japanese star on their team for reasons both financial and for future recruiting, so why not stick with Suzuki?
But in case you missed it, the only two real rumors we’ve had this “offseason” so far are not promising: (1) The Cubs are reportedly “unlikely” to win a bidding war for Seiya Suzuki, and (2) The deep-pocketed and motivated Toronto Blue Jays are “expected to pursue” Seiya Suzuki in free agency.
Still, I refuse to believe the Chicago Cubs seriously believe they can replace Ian Happ and Seiya Suzuki with Pedro Ramirez and Matt Shaw (neither of whom have proven anything close to the offensive floor, let alone upside of the above). And that’s without mentioning the hole they’d then leave on the bench, which, as we saw this season, was critical.
I can understand filling ONE of the outfield spots with Ramirez, Shaw, or some sort of platoon. But pencilling in both as your starting corner outfielders would be a huge mistake.
To that end, a couple more outfielders make the list.
Chicago Cubs right fielder Seiya Suzuki | Patrick Gorski-Imagn Images4. Randy Arozarena, OF (RHH)
Randy Arozarena is only a little bit younger than Suzuki, but he’s coming off a stronger offensive season and has never been a below-average hitter in MLB (128 career wRC+).
This past season, for the Mariners, Arozarena slashed .281/.381/.484 (151 wRC+) with 26 HRs, a 10.1% walk rate, and a 21.6% strikeout rate. There was definitely some good luck baked into those results (.333 BABIP in 2026 compared to .307 for his career), but the underlying stats looked mostly good.
I can definitely pick some modest red flags (lower bat speed, lower fast-swing rate, barrel rate was just average, etc.), but there are only so many bats with this sort of upside. So if Suzuki is off the table, Arozarena would be a nice target.
The big issue here is that his defense rates out pretty poorly every single year. In 2026, out of 54 qualified outfielders, Arozarena’s -2 DRS (34th), -5 OAA (44th), and -7 FRV (46th) paint the picture of a very poor defensive outfielder. And I just don’t know if this Cubs front office will ever really consider a guy like that (especially one at his age, when it will presumably get worse from here).
Seattle Mariners left fielder Randy Arozarena | Stephen Brashear-Imagn Images5. Michael King, SP (RHP)
As an older, right-handed, softer-tossing, lower-strikeout starter, Michael King is not anywhere close to the type of pitcher the Cubs should be hoping to acquire this offseason. That said, he’s still a fantastic starter. Or was this past season: 32 starts (185.0 IP) with a 3.21 ERA. He also limited hard contact well, kept the ball on the ground enough, and is just generally successful more times than not.
And like I said, the Cubs need a TON of starting pitching.
I also think we all saw what he was capable of in the Cubs/Padres NL Wild Card game this year … the guy has talent. He’s legit. I’d be thrilled if the Cubs could land him this winter. For what it’s worth, King will need to opt out of his two remaining player options for 2027 ($28M) and 2028 ($30M), though that seems likely. I don’t think he’ll get an AAV that high on his new deal, but the overall commitment should be dramatically higher.
San Diego Padres pitcher Michael King © Denis Poroy-Imagn Images6. David Peterson, SP (LHP)
This is the one time I am going to include a little bit of the financial side in the calculus of my rankings. But, yes, of all the pitchers the Cubs acquired this season, it is David Peterson (not Clay Holmes, not Kevin Gausman) I want to see back in Chicago next year.
Peterson is left-handed (check) and had more success in Chicago than anyone expected (and we DID expect a performance boost given his groundball rate and this infield defense).
With the entire Cubs infield defense returning again next season, Peterson feels like a no-brainer target for the Cubs. No, he’s not young (2027 will be his age-31 season), and no, he doesn’t throw hard (92.6 mph velo). But that impressive career groundball rate (and 55.2% GB rate from July 27 on) makes too much sense with this defense.
If he were the Cubs ONLY pitching acquisition, that’d be a problem. But as a second addition, at an expectedly lower cost, David Peterson is arguably ideal. I just hope we come to learn that he enjoyed his time and success in Chicago as much as we did.
Also, hey, for what it’s worth, it’s not like Peterson is a stranger to high-level success. He had a 2.90 ERA over 21 starts in 2024 and was an All-Star in 2025. There are some caveats I’m ignoring in both of those seasons, but that’s generally covered by my insistence that he cannot be THE big pitcher acquisition. Just one of them.
Chicago Cubs pitcher David Peterson | David Banks-Imagn ImagesOther MLB Free Agents
There are a lot more free agents who could make sense for the Cubs this offseason, but these seven strike me as the most critical and/or best fits. Those are the names to dream on, those are the positions/characteristics we need to be targeting.
Some of these holes could/will be filled internally; others perhaps via trade. But new CBA or not, the Cubs need to be very active in free agency again this winter. There are simply too many exiting players and too much of an existing, competitive core to be passive.
Alex Bregman is getting older every season and PCA is in the middle of his prime. Go nuts, Tom and Jed. If you don’t, we’ll just be in the same position (or worse) again next year.
And to conclude, here’s a full list of all the 2026-2027 MLB free agents by position (source: MLB.com)
CATCHERSRyan JeffersCarson Kelly (mutual option)Tyler StephensonAustin HedgesKyle Higashioka (mutual option)James McCannGary Sánchez (mutual option)Reese McGuireJake RogersChristian VázquezLuke MaileMitch GarverTravis d’ArnaudJonah Heim
FIRST BASEMENTy FranceJake BauersPaul GoldschmidtAndrew VaughnRhys HoskinsNathaniel LoweRowdy TellezDominic SmithCarlos Santana (mutual option)Ryan MountcastleChristopher Morel
SECOND BASEMENJazz Chisholm Jr.Brandon LoweLuis ArraezGleyber TorresOzzie Albies (club option)Jeff McNeil (club option)Isiah Kiner-FalefaAdam FrazierLenyn SosaIldemaro VargasGavin LuxNick MadrigalLuis UríasCavan BiggioJonathan IndiaDylan MooreBrendan RodgersKyle Farmer
THIRD BASEMENBo Bichette (opt-out)Eugenio SuárezEdmundo SosaAlec BohmRamón Urías (mutual option)Yoán MoncadaLuis Rengifo (mutual option)Amed RosarioSantiago EspinalKiké HernándezJeimer CandelarioLeo JiménezJosh Rojas
SHORTSTOPSMauricio DubónJ.P. CrawfordPaul DeJongZack ShortKevin NewmanOrlando ArciaJorge MateoHa-Seong Kim
LEFT FIELDERSRandy ArozarenaIan HappTaylor WardRamón LaureanoRandal GrichukAustin HaysJJ BledayMichael ConfortoSam HaggertyLourdes Gurriel Jr. (club option)Tommy PhamDylan CarlsonAlex Verdugo
CENTER FIELDERSTrent GrishamDaulton VarshoTyrone TaylorMyles Straw (club option)TJ FriedlCedric Mullins (mutual option)Luis Robert Jr. (club option)Lane Thomas
RIGHT FIELDERSSeiya SuzukiRonald Acuña Jr. (club option)Mike TauchmanAdolis GarcíaJake FraleyVictor Robles (club option)Starling MarteAustin SlaterNick Castellanos
DESIGNATED HITTERSGeorge SpringerMiguel Andujar (mutual option)Josh Bell (mutual option)Joc Pederson (mutual option)Marcell Ozuna (mutual option)Rob RefsnyderAndrew McCutchenJorge Soler
STARTING PITCHERSLHP Tarik SkubalRHP Drew Rasmussen (club option)LHP Trevor RogersRHP Kevin GausmanRHP Sonny Gray (mutual option)RHP Freddy PeraltaLHP Matthew Boyd (mutual option)RHP Nick Pivetta (opt-out)RHP Sandy Alcantara (club option)RHP Nick Martinez (mutual option)LHP David PetersonRHP Casey MizeLHP Kris BubicRHP Tyler MahleRHP Jack FlahertyRHP Michael Soroka (mutual option)RHP Clay Holmes (opt-out)RHP Michael King (opt-out)RHP Luis Severino (player option)RHP Dustin May (mutual option)RHP Chris BassittLHP Robbie RayRHP Brady SingerRHP Brandon WoodruffLHP Shota ImanagaLHP Foster GriffinLHP Martín PérezRHP Colin Rea (club option)RHP Cal QuantrillRHP Aaron CivaleRHP Lucas Giolito (mutual option)LHP Jeffrey Springs (club option)RHP Michael LorenzenRHP José Berríos (opt-out)RHP Trevor WilliamsLHP Patrick SandovalRHP Walker BuehlerRHP Griffin Canning (mutual option)RHP Zac GallenRHP Max ScherzerLHP Jose QuintanaRHP Tatsuya Imai (opt-out)RHP Tomoyuki SuganoRHP José UrquidyRHP Shane BieberRHP Corbin Burnes (opt-out)RHP Zack Littell (mutual option)RHP Luis GarciaLHP Jordan MontgomeryRHP Jameson TaillonRHP Taijuan WalkerRHP Frankie MontasRHP Lance McCullers Jr.RHP Zach Eflin (mutual option)RHP Tony Gonsolin (club option)RHP Erick FeddeLHP Austin GomberRHP Germán MárquezRHP Miles Mikolas
RELIEF PITCHERSLHP Adrian MorejonRHP Garrett Whitlock (club option)RHP David BednarLHP Sean NewcombLHP Steven OkertRHP Andrés Muñoz (club option)LHP Tyler AlexanderRHP Raisel IglesiasLHP Alex VesiaLHP Gregory SotoRHP Bryan AbreuRHP Emilio Pagán (opt-out)RHP Shawn Armstrong (mutual option)RHP Andrew KittredgeLHP Brooks RaleyRHP Mark Leiter Jr.RHP Jason AdamRHP Emmanuel Clase (club option)LHP JoJo RomeroLHP José AlvaradoLHP Brock BurkeRHP Kevin GinkelRHP Jakob Junis (mutual option)RHP Paul BlackburnRHP Taylor ClarkeRHP Carlos Estévez (club option)RHP Pete FairbanksLHP Hoby MilnerLHP Wandy Peralta (player option)RHP Dennis SantanaRHP Antonio Senzatela (club option)LHP Caleb Thielbar (mutual option)RHP Kenley Jansen (club option)LHP José SuarezLHP Brent SuterLHP Ryan YarbroughRHP Drew Anderson (club option)RHP Enyel De Los SantosLHP Caleb FergusonLHP Kolby AllardLHP Dietrich Enns (club option)RHP Jonathan LoáisigaLHP Danny CoulombeRHP Luis GarcíaRHP Tyler KinleyRHP Evan PhillipsRHP Ryan ThompsonRHP Justin TopaRHP Jacob Webb (club option)LHP Andrew ChafinLHP Kyle Hart (club option)LHP A.J. MinterRHP Ryan BrasierRHP Hunter Harvey (mutual option)RHP Chris MartinLHP Taylor RogersLHP Matt StrahmRHP Ryan Helsley (opt-out)RHP Pierce Johnson (mutual option)LHP Sam MollRHP John SchreiberRHP Blake TreinenRHP Yimi GarcíaLHP Yuki Matsui (opt-out)RHP Rafael MonteroRHP Jordan RomanoRHP Ryne Stanek (club option)RHP Robert Stephenson (club option)RHP Matt BowmanRHP Brusdar GraterolRHP Joe JiménezLHP Drew PomeranzLHP A.J. PukRHP Tanner RaineyRHP Drew SmithRHP Trevor Stephan (club option)RHP Hunter StricklandRHP Rowan Wick (club option)RHP Jake WoodfordLHP Jalen BeeksLHP Ryan BoruckiRHP Lou Trivino IIIRHP Dan AltavillaRHP Chris DevenskiRHP Luke JacksonRHP José LeclercRHP Tommy KahnleRHP Joe RossLHP Keegan AkinRHP Jorge AlcalaRHP Scott BarlowLHP Aaron BummerRHP Paul SewaldRHP Ryan Weiss (club option)RHP Trent ThorntonLHP Génesis CabreraLHP Tim Hill
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