Cubs Rumors

Cubs Sign Colin Rea To One-Year Extension

By Anthony Franco | November 6, 2025 at 11:05am CDT

11:05am: The Cubs have officially announced Rea’s contract. MLB.com’s Jordan Bastian broke down the contract structure, noting that Rea will earn $5.5MM in 2026 with a $1MM buyout on a $7.5MM club option.

7:24am: The Cubs have hammered out a restructured deal with right-hander Colin Rea, reports MLBTR’s Steve Adams. It’s a $6.5MM guarantee that includes a club option for the 2027 season and maxes out at $13MM over two years if that option is exercised. Rea is represented by Joe Speed.

Chicago had previously held a $6MM option or a $750K buyout for the upcoming season. The new deal supersedes the buyout, so Rea technically picks up $5.75MM in new money. That’s more than the $5.25MM difference between the option price and the buyout. Rea gets an extra $500K overall, while the Cubs secure an extra year of team control.

The 35-year-old Rea is coming off a solid season. He signed as a swingman and was pressed into the rotation by the middle of April because of the season-ending injury to Justin Steele. Rea was generally good for 5-6 competitive innings each time out. He turned in a 3.95 earned run average while ranking second on the team with 159 1/3 innings. Rea had a pedestrian 19.2% strikeout rate but he rarely issues free passes and did a decent job keeping the ball in the yard.

It’s the third straight season in which Rea has been a capable fifth/sixth starter. He spent the 2023-24 campaigns with the Brewers, combining for a 4.40 ERA with a near-20% strikeout percentage in a little less than 300 innings. Only Freddy Peralta threw more innings for Milwaukee over that two-year stretch. Rea’s flexibility has clearly endeared him to Craig Counsell, who managed him with the Brewers in 2023 and this year with Chicago.

Second-year righty Cade Horton projects as the team’s top starter at the moment. They could get Steele back at some point in the first half. Matthew Boyd, Jameson Taillon and Rea are in the mix at the middle to back end. Javier Assad, Jordan Wicks and Ben Brown could compete for back-end spots (though the Cubs might commit to Brown as a full-time reliever sooner than later).

It’s clearly a light group for a playoff team. The Cubs figure to take a swing for at least a #2 or high-end #3 arm via trade or free agency. That’s all the more true after they declined their three-year option on Shota Imanaga. While there’s a slim chance Imanaga returns if the Cubs make him a qualifying offer, that decision seems to signal that the Cubs are aiming higher in their rotation targets.

The Cubs opened the ’25 season with a player payroll just under $193MM. RosterResource projects them around $154MM, including arbitration estimates, going into next season. They’re more than $70MM shy of the luxury tax threshold. The Rea extension nearly closes the book on the team’s option decisions. Their only remaining one is a $10MM mutual option for Justin Turner. The Cubs will easily decline their end in favor of a $2MM buyout.

Image courtesy of Michael McLoone, Imagn Images.

Justin Turner Becomes Free Agent

By Nick Deeds | November 6, 2025 at 9:12am CDT

Infielder Justin Turner is headed into free agency after his mutual option with the Cubs was declined, according to an announcement by the Major League Baseball Players Association this morning. It’s not clear who between Turner and the Cubs declined their end of the option, but either way Turner will be paid a $2MM buyout rather than a $10MM salary for 2026.

Turner, 41 later this month, had his first below-average season in over a decade in 2025. The veteran hit just .219/.288/.314 with a wRC+ of 71 in across 80 games and 191 plate appearances. He was largely a bench player for the Cubs this past season, with his primary role in Chicago being to serve as a platoon partner for the lefty-swinging Michael Busch at first base.

In that specific role, Turner actually did reasonably well for himself. He slashed .276/.330/.429 (112 wRC+) in 109 plate appearances against left-handed pitching. That’s a perfectly solid number, but it’s belied by atrocious numbers against same-handed pitching. Righties limited Turner to a slash line of just .141/.232/.155 with a wRC+ of just 16 in 82 trips to the plate. That’s the worst production against right-handed pitching among hitters with at least 70 trips to the plate against righties this year, and it left Turner with negative WAR according to both Fangraphs and Baseball Reference this year.

As Turner nears his 41st birthday, he hasn’t indicated one way or another what his plans are for the future. If he looks to continue his playing career, it’s not hard to imagine a team valuing his experience and leadership in the clubhouse enough to give him an invitation to Spring Training and allow him to compete for a bench role despite his rough 2025 campaign. With that being said, a big league guarantee on the level he received last offseason is hard to imagine, and he’d mostly only fit on a roster that struggles badly at the plate against southpaws.

As for the Cubs, they’ll be looking to largely overhaul their bench mix this winter. Turner and Willi Castro are both headed into free agency, while Reese McGuire is a potential non-tender candidate. A platoon partner for Busch may not be quite as necessary as it seemed this time last year after his breakout 2025 season where he posted a 140 wRC+ and even managed to post a 143 wRC+ against southpaws from July 1 onward. That’s a sample of just 52 plate appearances, however, and if the Cubs do want some insurance they could turn to someone like Wilmer Flores, Ty France, or Connor Joe.

MLBTR Podcast: Offseason Preview Megapod: Top Trade Candidates

By Darragh McDonald | November 5, 2025 at 11:58pm CDT

The latest episode of the MLB Trade Rumors Podcast is now live on Spotify, Apple Podcasts, and wherever you get your podcasts! Make sure you subscribe as well! You can also use the player at this link to listen, if you don’t use Spotify or Apple for podcasts.

This week, host Darragh McDonald is joined by Steve Adams and Anthony Franco of MLB Trade Rumors to discuss…

The 2025 World Series between the Dodgers and Blue Jays (1:55)
The Cubs letting Shota Imanaga becoming a free agent (9:05)
Ha-Seong Kim opting out of his deal with the Braves (19:00)
MLBTR’s list of the Top 40 Trade Candidates for the offseason (28:15)
The Cardinals having six guys on the list (32:15)
Why the Nationals will likely make MacKenzie Gore and CJ Abrams available (42:40)
The Twins, Joe Ryan, Pablo López and Ryan Jeffers (54:05)
The Pirates have a bunch of pitchers they could trade (1:06:20)
The Rays, Pete Fairbanks and Brandon Lowe (1:18:05)
The Brewers and Freddy Peralta (1:25:50)
The Marlins having some arms who could move (1:31:50)
Tyler Soderstrom of the Athletics, who did not make the list (1:41:40)
A theoretical trade sending Brady Singer to the Angels and Taylor Ward to the Reds (1:47:20)

Check out our past episodes!

Bo Bichette’s Health, Kazuma Okamoto, And Dylan Cease’s Market – listen here
The Phillies’ Outfield, Tarik Skubal, And Hiring College Coaches – listen here
Murakami To Be Posted This Offseason, Managerial Vacancies, And More! – listen here

The podcast intro and outro song “So Long” is provided courtesy of the band Showoff. Check out their Facebook page here!

Photo courtesy of Jeff Curry, Imagn Images

Cubs Not Expected To Pursue Top Free Agent Relievers

By Nick Deeds | November 5, 2025 at 11:51am CDT

The Cubs are going to need to overhaul their bullpen this winter after trading Andrew Kittredge to the Orioles yesterday while Brad Keller, Drew Pomeranz, and Caleb Thielbar are all ticketed for free agency. Despite those four departures draining their entire high-leverage relief mix outside of Daniel Palencia, however, Sahadev Sharma of The Athletic reports that Chicago’s front office is not expected to be involved in the markets of this winter’s top free agent relief arms.

That’s not especially surprising, as the Cubs have generally eschewed high-dollar multi-year deals for relievers over the years. There have been some rare exceptions to that rule, such as the three-year deal the Cubs signed Craig Kimbrel to in 2019 while Theo Epstein was in charge and the team’s pursuit of southpaw Tanner Scott in free agency under Jed Hoyer last offseason, but the Cubs have long preferred to build their bullpen on a budget. That includes last year’s group. Keller was a non-roster invitee to Spring Training, Pomeranz was acquired from the Mariners in a minor trade back in April, and Thielbar’s big league deal guaranteed him just $2.75MM total. Those three pitchers posted ERAs of 2.07, 2.17, and 2.64 respectively while combining for 177 1/3 innings across 192 appearances.

Sharma suggests that trying to find value on the margins of the market with minor league deals and reclamation projects figures to be the club’s goal once again this winter, though he does leave the door open for the possibility that the Cubs could jump into the market on a bigger name relief arm if their expected market doesn’t materialize and they linger into January and February. Otherwise, it seems as though the Cubs won’t be adding a top tier closer this winter. Sharma specifically names Edwin Diaz, Robert Suarez, and Devin Williams as players who aren’t likely to be in the cards for Chicago at this point.

That doesn’t mean they won’t add any veterans who can offer some more certainty towards the back of the bullpen, of course. Sharma notes that the club brought in Ryan Pressly via trade this past offseason in an effort to provide that sort of certainty. Pressly was on the last year of his deal, and it seems likely that if the Cubs do add a bullpen veteran on a notable deal, it would be a similar one-to-two year arrangement. That could come via either free agency or trade; perhaps the Rays would make Pete Fairbanks available on the trade market ahead of his final year under club control, or the team could try and pursue a one-year deal with a veteran closer like Kenley Jansen.

It’s possible the club could be banking on some internal improvements to their relief corps, as well. Any number of young arms might be able to take a step forward similar to the one Palencia made this past season, and with the Cubs seemingly likely to pursue starting pitching additions this winter, that could make converting a young rotation arm like Ben Brown into relief full-time a viable option. Brown is held back as a starter by a lack of a quality third pitch, but he did strike out 28.6% of his opponents with a 2.97 FIP after moving into a bullpen role to open the month of August. Porter Hodge and Luke Little are among the other arms in the club’s relief corps who have shown flashes of dominance at the big league level but have yet to put it all together consistently.

Orioles Acquire Andrew Kittredge From Cubs

By Mark Polishuk | November 4, 2025 at 1:05pm CDT

The Orioles have reunited with Andrew Kittredge, as the team announced that the right-hander has been acquired from the Cubs in exchange for cash considerations. While not mentioned in the Orioles’ press release, it can be assumed that the O’s will be exercising Kittredge’s $9MM club option for the 2026 season rather than swinging a trade for the reliever just to buy him out for $1MM.

Last January, Kittredge came to Baltimore for the first time when he signed a one-year deal worth $10MM in guaranteed money — a $9MM salary for 2025, and the $1MM in buyout money. A debridement procedure in his left knee delayed Kittredge’s 2025 debut until late May, but he was in fine form afterwards, and he became an obvious trade candidate when the O’s fell out of contention. The result was a deal to the Cubs at the trade deadline, with Baltimore netting infield prospect Wilfri De La Cruz in return.

Kittredge’s overall numbers were even better in Chicago after the trade, and he made five appearances for the Cubs in the postseason. For 2025 as a whole, Kittredge posted a 3.40 ERA and a superb set of advanced metrics. His 30.8% strikeout rate and 5.3% walk rate each sat in the 92nd percentile of all pitchers, his 49.2% grounder rate was far above average, and his 41.6% chase rate was the best of any pitcher in baseball.

Today’s trade means that the Orioles have now gotten Kittredge and De La Cruz in their organization, plus they saved roughly $2.8MM in salary when the Cubs took on the remainder of Kittredge’s 2025 salary. Had everything gone to plan for Baltimore this season, the team surely had an eye towards exercising Kittredge’s club option anyway, so they’ll now get to make that decision after all and address a bullpen need.

Felix Bautista will miss most or all of the 2026 season recovering from shoulder surgery, plus Kittredge was one of several relievers dealt away by the Orioles at the deadline. Even with Kittredge’s contributions, Baltimore’s bullpen was one of the weakest in the league in 2025, and rebuilding the relief core seems to be one of the club’s top priorities this offseason.

From the Cubs’ perspective, passing the buck (literally and figuratively) on Kittredge’s club option seems like an unusual move. While Kittredge is entering his age-36 season and Chicago has traditionally been wary about overspending on relief pitching, $9MM seems like a fairly safe investment given how well Kittredge performed in 2025. The Wrigleyville bullpen was quite solid this year, yet since many names from that group are free agents, exercising Kittredge’s club option would’ve been a way for the Cubs to partially solidify things early in the winter.

Since Shota Imanaga’s three-year club option was also declined by the Cubs earlier today, quite a bit of projected money has now been cleared off the team’s books between Imanaga and Kittredge. As per RosterResource, Chicago has an estimated 2026 payroll of roughly $148.3MM and a luxury tax number of $164MM — well below their $206.4MM payroll and $227.3MM tax figure from 2025. While Wrigleyville fans have a right to be concerned over how much ownership is willing to spend, this situation could mean that the Cubs are making room for a bigger-ticket acquisition or two this offseason.

Shota Imanaga Becomes Free Agent

By Nick Deeds | November 4, 2025 at 8:12am CDT

Left-hander Shota Imanaga has become a free agent, according to a report from Jesse Rogers of ESPN. The Cubs declined their three-year, $57MM club option on Imanaga’s services for 2026-28, and Imanaga subsequently declined his $15MM player option for 2026.

It’s an outcome that would’ve seemed unthinkable just a few months ago. Signed out of Japan to a deal that was on paper a four-year, $53MM contract during the 2023-24 offseason that had the aforementioned complex option structure set to kick in after the 2025 campaign, Imanaga was nothing short of sensational for Chicago in his first year as an MLB pitcher last year. In 29 starts, he pitched to a 2.91 ERA with a 25.1% strikeout rate across 173 1/3 innings of work that earned him an All-Star appearance and a fifth-place finish in NL Cy Young award voting last year.

While that strong rookie campaign seemed to portend a long stay near the front of Chicago’s rotation for Imanaga, things started to unravel this year. Early in the season, he managed to get strong results despite shoddy peripherals, with a 2.82 ERA through eight starts despite a 4.59 FIP and a strikeout rate that had plummeted to just 18.8%. His season was abruptly put on hold by a hamstring injury that cost him nearly two months, and when he returned his strikeout rate continued to dip. He did manage to fire off seven scoreless innings with five strikeouts during his first start after the All-Star break, but from there he began a downward spiral where his results started to match his lackluster peripherals.

From July 25 through the end of the season, Imanaga made 12 starts where he surrendered a 5.17 ERA with a 5.42 FIP across 69 2/3 innings of work. His strikeout rate actually recovered a bit during this stretch, creeping back up to 23.2%, but he allowed an eye-popping 20 home runs in that stretch. Imanaga has always had trouble with the long ball, and even in his excellent 2024 campaign he allowed the tenth-most homers among qualified starters. This year, his 31 homers allowed were the fourth-most in all of baseball despite him pitching just 144 2/3 frames. That’s fewer innings than anyone else in the top 20 besides Tyler Anderson, who allowed 28 homers in 136 1/3 innings of work.

In spite of his lackluster season, a poll of MLBTR readers on September 10 suggested that more than 91% believed the Cubs should exercise his club option. From that point onward, what seemed at the time like a borderline call became more clear as he posted an 8.04 ERA in his final three regular season starts before posting an 8.10 ERA in the postseason and ultimately being passed over for a winner-take-all Game 5 start against the Brewers in the ALDS despite him being on regular rest. By that time, this outcome seemed far more likely. MLBTR’s Tim Dierkes took a guess at Imanaga’s future in our Offseason Outlook coverage of the Cubs on October 22, and settled on the sides both declining their options and Imanaga heading into free agency.

From the Cubs’ perspective, moving on from Imanaga is understandable for a handful of reasons. By picking up his option, the Cubs would be counting on Imanaga to rebound into at least mid-rotation form for his age-32, -33, and -34 seasons. That might not seem like a bad bet to make, but it’s worth noting that Wrigley Field is notoriously fickle in terms of park factors thanks to the wind. In 2024, when Imanaga was at his best with the Cubs, Wrigley suppressed home runs at the fifth-highest rate in all of baseball according to Statcast. This year, that inverted to make the Friendly Confines the 11th-friendliest ballpark in baseball to home run hitters.

Perhaps Imanaga will be able to return to form elsewhere, particularly if he signs in a park with more consistent homer-suppressing tendencies, but it’s not hard to see why the Cubs wouldn’t want to commit to him long-term given that reality. That doesn’t necessarily rule out the possibility that he’ll return to the Cubs at all; Rogers reports that it’s not yet clear if Chicago intends to extend Imanaga the qualifying offer. Recouping draft pick compensation for Imanaga if he departs would surely be attractive to the Cubs, and him accepting the QO may be preferable to having kept him on a three-year deal at a lower annual cost due to the short-term nature of the arrangement. With that said, the market has plenty of mid-rotation or better starters available this winter, and the Cubs might prefer to not risk Imanaga accepting the offer so they can reallocate those dollars to a starter they feel better fits their roster.

Yoervis Medina Passes Away

By AJ Eustace | October 31, 2025 at 6:44pm CDT

Former major league pitcher Yoervis Medina has passed away. Reports out of his native Venezuela indicate that authorities believe Medina suffered a heart attack while he was driving, leading to a fatal car accident. He was 37 years old.

Medina pitched for the Mariners and Cubs from 2013-15, working 146 innings across an identical number of games. He posted a 3.08 career ERA with a 23.1% strikeout rate along with a 12.4% walk rate. Most of his success came in his first two seasons, as Medina pitched to a 2.81 ERA with a 24.3% strikeout rate and 12.6% walk rate in 125 innings for the Mariners from 2013-14. In that span, he ranked 34th out of 109 qualified relievers in ERA and ranked 21st with a 53.5% ground ball rate.

He was traded to the Cubs in May 2015 for Welington Castillo and pitched in five games for them with a 7.00 ERA, but he wound up spending most of the season in the minors. That was followed by brief stints in the Pirates and Phillies organizations in 2016, neither of which resulted in a big league call. Medina then pitched in the Venezuelan winter league from 2016-20 before moving to the Italian Baseball League in 2023 and the Czech Baseball Extraliga in 2024.

Medina was teammates in Seattle with Jesús Montero, who was tragically killed in a motorcycle crash earlier this month. We at MLB Trade Rumors send our condolences to Medina’s family, friends, loved ones and former teammates.

AL East Notes: Story, Flaherty, Lowe, Fairbanks

By Mark Polishuk | October 29, 2025 at 12:50pm CDT

MassLive.com’s Chris Cotillo and Sean McAdam touched on an assortment of Red Sox topics in the latest edition of their Fenway Rundown podcast, including a brief mention of Trevor Story’s status as the shortstop considers an opt-out clause in his contract. Cotillo believes “the Red Sox are pretty cautiously very optimistic that” Story will be staying with the team, and while’s plenty of grey area within that statement, it does offer some indication that Story is leaning towards declining his opt-out.

Story is owed $25MM in each of the next two seasons, plus there’s a $5MM buyout on his $25MM club option for the 2028 campaign. The Red Sox can override Story’s opt-out by guaranteeing that 2028 club option right now, but that doesn’t appear to be on the team’s radar, so the ball looks to be entirely in Story’s court. While Story’s .263/.308/.433 slash line and 25 homers over 654 plate appearances only translates to a 101 wRC+, his numbers were weighed down by a cold start to the season, as Story posted an .825 OPS over his final 429 PA.

Between this strong finish and a thin free agent shortstop market, there’s a case for Story to leave his $55MM guaranteed on the table and look for a bigger contract this winter. On the flip side, Story turns 33 next month, his defensive metrics were subpar, and the injury problems that plagued him in 2022-24 will be on the minds of front offices even though Story stayed pretty healthy in 2025. If Story wants to avoid the risks of another prolonged stint in free agency, staying in Boston with a contending Red Sox team certainly seems like a viable choice.

MLBTR Podcast: Bo Bichette’s Health, Kazuma Okamoto, And Dylan Cease’s Market

By Darragh McDonald | October 29, 2025 at 10:15am CDT

This week, host Darragh McDonald is joined by Steve Adams of MLB Trade Rumors to discuss…

The Blue Jays getting Bo Bichette back for the World Series as he is on the cusp of free agency (2:45)
Kazuma Okamoto to be posted for MLB clubs this offseason (10:45)
The free agent market for Dylan Cease, who has interest from the Cubs (20:10)
The Orioles hiring Craig Albernaz and the Angels hiring Kurt Suzuki for their managerial vacancies (34:45)

Plus, we answer your questions, including…

If the Blue Jays were to extend Addison Barger, would the Lawrence Butler deal be a good comp? (40:35)
If a veteran signs a minor league deal, are they eligible to be taken in the Rule 5 draft? (44:50)
Will the Red Sox trade Jarren Duran? (46:25)

Check out our past episodes!

The Phillies’ Outfield, Tarik Skubal, And Hiring College Coaches – listen here
Murakami To Be Posted This Offseason, Managerial Vacancies, And More! – listen here
Rockies’ Front Office Changes, Skip Schumaker, And ABS Talk – listen here

The podcast intro and outro song “So Long” is provided courtesy of the band Showoff. Check out their Facebook page here!

Photo courtesy of Dan Hamilton, Imagn Images

Extension Candidate: Pete Crow-Armstrong

By Nick Deeds | October 26, 2025 at 3:06pm CDT

Few players captured more attention throughout the 2025 season than Pete Crow-Armstrong. The young center fielder seemed to launch himself into superstardom in the first half this year, with 20 doubles, 21 homers, and 25 steals through the end of June. That worked out to a .263/.299/.537 slash line, good for a 128 wRC+ with elite defense in center field that made him an early rival for Shohei Ohtani in this year’s MVP race. He followed up that brilliant performance with a far less exciting second half, as he slashed just .228/.274/.412 (86 wRC+) with 17 doubles, ten home runs, and ten steals from July 1 onward.

Crow-Armstrong’s second-half slump was enough to knock him far out of the MVP conversation, but his season-long numbers remain impressive. In 157 games, the 23-year-old hit .247/.287/.481 (109 wRC+) with 35 steals in 43 attempts and an MLB-best +24 Outs Above Average for his work in center field. All of that combined to be worth 6.0 bWAR and 5.4 fWAR, good for 11th and 15th respectively among qualified hitters this year. A five- or six-win season from a 23-year-old who entered the year with less than 150 games of big league experience is hard to view as anything other than an exciting success, and that’s how Jed Hoyer characterized it in his end-of-season press conference shortly after the Cubs’ season came to a close in Game 5 of the NLDS.

“In totality, he had a great year,” Hoyer said of Crow-Armstrong, as relayed by Patrick Mooney of The Athletic. Hoyer went on to describe Crow-Armstrong as “the best defensive player in baseball” and noted that “when he’s hitting, he’s a superstar.”

All of that rings true based on his performance this season, and as the Cubs head into an offseason where Hoyer acknowledged they hope to have extension conversations with several players, Mooney writes that locking up the team’s star center fielder “figures to be the top priority.”

It won’t be the first time the Cubs and Crow-Armstrong talk about extending his stay in Chicago beyond his years of team control. The sides discussed an extension towards the beginning of the year, before his standout first half, and Crow-Armstrong passed on a deal that reportedly would’ve maxed out around $75MM with a guarantee in the $60MM-$70MM range. Crow-Armstrong, of course, rejected that offer, and while Hoyer expressed an openness to discussing an extension with the youngster’s camp during the season no further progress on the topic was reported throughout the year. Perhaps that’s not surprising, given the unusual year Crow-Armstrong just had.

If the Cubs do intend to reopen extension talks with their budding star, what could a sensible contract look like? After entering 2025 just barely short of a full year of MLB service time, Crow-Armstrong currently remains under control through the end of the 2030 season. At that point, he figures to be ticketed for free agency ahead of his age-29 campaign. A look at MLBTR’s Contract Tracker offers a wide range of comparable players in recent years. Players like Ke’Bryan Hayes, Lawrence Butler, and Ezequiel Tovar had less than two years of MLB service when they signed their deals, like Crow-Armstrong. They all landed extensions in the $60MM to $70MM range that the Cubs reportedly offered prior to this season, but those deals were blown out of the water by the $134.2MM guarantee Jackson Merrill landed in his eight-year extension with the Padres back in April.

Merrill is a year younger than Crow-Armstrong, meaning he signed his deal at the start of his age-22 season while Crow-Armstrong would be signing ahead of his age-24 season this offseason. Both players had five seasons left under club control before free agency, however, and were coming off similarly elite platform seasons; Merril’s 130 wRC+ outshone Crow-Armstrong, but his lesser defense and baserunning left him with a roughly comparable 5.3 fWAR. They also play the same position, making Merrill’s recent deal a logical point of reference for Crow-Armstrong overall.

It’s the second-highest guarantee an outfielder with less than two seasons of MLB service time has received in MLB history, behind the $210MM guarantee the Mariners offered Julio Rodriguez that can max out at $470MM over 17 years if all incentives are reached and options are exercised. Given that Rodriguez was in the midst of posting a 148 wRC+ with 5.7 fWAR and 6.2 bWAR in just 132 games as a 21-year-old rookie when he signed his extension, it’s safe to expect that a deal for Crow-Armstrong would come in closer to Merrill’s contract.

A contract similar to the one signed by Merrill could make some sense, and an eight-year, $140MM contract would beat Merrill’s contract in terms of both guarantee and average annual value. However, the Cubs may not be interested in such a large guarantee for only three additional seasons of team control, while Crow-Armstrong may not want to head into free agency at the tail end of his physical prime as a player who derives as much value from speed and defense.

Then, perhaps, the sides could get together on a longer contract that would buy out more free agent years. An 11-year deal that runs through the 2036 season would keep Crow-Armstrong in town for the rest of his prime and buy out six free agent years. An 11-year, $187MM guarantee would narrowly eclipse Merrill by both guarantee and AAV, while also narrowly beating out the eight-year, $184MM contract the Cubs gave Jason Heyward during the 2015-16 offseason for the largest deal in franchise history.

It would be a risky investment given Crow-Armstrong’s lackluster plate discipline, which left him with the third-highest swinging-strike rate in the majors this year. Given that risk and the fact that Crow-Armstrong is not set to even reach arbitration until next winter, it would be understandable if the Cubs decided to wait and see how the 2026 season played out before committing that sort of money to their center fielder.

On the other hand, the upside in Crow-Armstrong’s profile is obvious and Chicago’s reluctance to spend at the top of the market on free agents in recent years could mean that waiting another year could put Crow-Armstrong out of Chicago’s price range entirely. Rolling the dice on an extension for Crow-Armstrong could be the team’s best bet of securing a long-term, star-caliber talent. Meanwhile, it would be understandable if Crow-Armstrong was motivated to lock in long-term financial security ahead of a 2026-27 offseason where a contentious round of collective bargaining over the sport’s economic future is widely expected.

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