The Chicago Cubs have had a very eventful offseason and, in a lot of ways, have changed the narrative regarding their ownership being irredeemably frugal and conservative with spending.
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They went out and pulled a daring trade for emerging power pitcher Edward Cabrera, dealing away three prospects, including no. 1 prospect Owen Caissie.
They signed free agent third baseman Alex Bregman to a 5-year, $175 million contract.
They also restocked a deplete bullpen with four new free agent relievers and several depth pieces below them.
All told, the Cubs spent over $220 million this offseason on acquiring new talent and re-signing holdovers from last season.
But the work’s not completely done for a squad that hopes to compete for a championship in 2026.
The last piece of the Cubs’ 2026 puzzle
Oct 8, 2025; Chicago, Illinois, USA; Chicago Cubs left fielder Ian Happ (8), center fielder Pete Crow-Armstrong (4) and right fielder Seiya Suzuki (27) celebrate after defeating the Milwaukee Brewers in game three of the NLDS round for the 2025 MLB playoffs at Wrigley Field. Mandatory Credit: Matt Marton-Imagn Images
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Maybe the biggest remaining question mark on the roster can be found in the outfield, one notch below starters Ian Happ, Pete Crow-Armstrong, and Seiya Suzuki. To be precise, there’s pretty much nobody in the fourth outfielder spot who can spell the three starters and take their position in case of injury.
Currently penciled into that role is the 23-year-old Kevin Alcantara, who has played all three outfield positions in the minors. He hasn’t shown, however, an ability to play every day in the majors. The Cubs also picked up Dodgers castoff Justin Dean, who looks to be a no-bat, all-speed player. They’re also talking about using Matt Shaw as an outfield backup this season.
So, with an apparent willingness to spend and, also, a willingness to drift just above the luxury tax threshold, could the Cubs dip into the free agency pool once again for a quality fourth outfielder?
One more free agent this year?
Sep 3, 2025; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates designated hitter Andrew McCutchen (22) circles the bases on a solo home run against the Los Angeles Dodgers during the second inning at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images
Jake Misener of Cubbies Crib is pushing for the Cubs to sign the 39-year-old Andrew McCutchen for that role:
“Andrew McCutchen is universally loved – and that’s coming from a site dedicated to a team he’s had plenty of big moments against in his 17-year MLB career. At age 39, his best days are behind him. But that doesn’t mean he doesn’t still have something to offer.
Last year with Pittsburgh, McCutchen slashed just .239/.333/.367, slightly below average in terms of wRC+ and OPS+, but still serviceable if you’re thinking of him as a veteran bench piece heading into 2026. The Cubs’ bench was abysmal last year and adding someone like the former 2013 NL MVP could, again, not only provide another veteran leader but also bolster the outfield depth.”
Pulling McCutchen from the Pirates
Aug 23, 2025; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates designated hitter Andrew McCutchen (22) hits a two run home run against the Colorado Rockies during the second inning at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images
McCutchen, by all accounts, wants to remain with the Pittsburgh Pirates, but the new-look Pirates, apparently, aren’t burning with desire to re-sign him. The mega-veteran has played the vast majority of his games recently at DH (120 in 2025, 113 in 2024), but he insists that he can still go out and play the field.
He even felt the need to recently jump on social media to defend his ability to still play defense against public statements claiming otherwise:
“It is really funny how so many ppl say I ‘Can’t(key word) play defense.’ I haven’t played much defense because they haven’t asked that of me. The only reason I played a few games last year is because Reynolds needed rest from a minor injury and I ASKED to play defense to get in the lineup. No one said anything then? Bottom line is if it is needed, I can not only do it, but do it like I’ve been out there all year. So stop creating false narratives and take your wives or GFs out to dinner and get off the coat tails of other men. That’s weird energy.”
McCutchen has played the last three seasons on $5 million-per-season deals. His price will likely drop a bit heading into 2026 after a season where he hit .239.
On the Cubs, he’ll get his wish to play the field again, albeit as a backup and/or emergency fill-in. He might also be able to return to postseason play for the first time since 2018, when he was with the Yankees.
Clearly, at 39, his best days are well behind him and the Cubs will be in trouble if he has to start more than a handful of games in the outfield in 2026. But he’s still got some pop from the right side of the plate and he has a wealth of experience, as well as a reputation as a great clubhouse presence. Why not grab him from an indifferent Pirates team?
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