5 Cubs trades that would break the internet if they happened

If Kyle Tucker chases the money (as is his right as a free agent), it's hard to imagine the Chicago Cubs are the ones writing the check and (re)introducing him at a press conference this winter. But that doesn't mean Jed Hoyer can't leave his mark on the offseason.

After balking in a series a trade talks back in July after he deemed asking prices well beyond reasonable, the recently-extended Cubs president of baseball operations could flex a little this winter by pulling off a blockbuster trade. Here are 5 trades he could make that would set the league ablaze.

5 Cubs trades that would break the internet if they happened

Tarik Skubal

The fact the Detroit Tigers are shopping Tarik Skubal who, in a few short weeks, will win his second straight AL Cy Young Award. A new report from The Athletic pegs his price tag in free agency at $400+ million - so if you're a team like the Cubs, acquiring the lefty would be a pure rental.

That being said, the Tigers would command a king's ransom for their prized ace. Over the last two years, he's been the most valuable pitcher in baseball: a 12.6 fWAR to go along with a 2.30 ERA/2.47 FIP over nearly 400 innings of work. Slotting him in atop the Chicago rotation would immediately help offset the loss of Tucker, making a path where the Cubs lean on their youth a bit more offensively more tenable.

Projected to earn $17.8 million in arbitration, Chicago could easily absorb that money - even if they bring Shota Imanaga back. This trade would bring pure ecstasy to Wrigleyville, while simultaneously feeling like a gut punch for a Tigers fanbase still reeling from the team's second-half collapse.

Hunter Greene

Looking for ace-level production but unwilling to part with a ton of top prospects for a rental? Then Hunter Greene may be more up your alley. The Cincinnati Reds right-hander is under team control through 2029 for just $61 million thanks to the extension he signed with the team in 2023 and multiple reports suggest Cincinnati will shop him this winter.

This year, Greene followed up his breakout 2024 with another strong showing, posting a 2.76 ERA in 19 starts, showcasing some of the best control of his career to go along with his overpowering arsenal. Having just turned 26 in August, the right-hander is heading into what should be the best years of his career.

The elephant in the room for the Cubs, though, is it seems highly unlikely Reds president of baseball ops Nick Krall is looking to trade Greene to a division rival or that Hoyer wants to see guys like Owen Caissie, Moises Ballesteros and Kevin Alcantara suiting up for Cincinnati for much of the next decade. That same logic can be applied to the next name on this list, as well.

Freddy Peralta

I will never again hear Freddy Peralta's name and not think about the incredible Wrigley Field crowd during his Game 4 start in the NLDS. That being said, I wouldn't be mad about having him in the Cubs' rotation next year - especially at a meager $8 million price tag.

This year, Peralta anchored the Brewers' rotation, leading the league with 17 wins and working to a 2.70 ERA in a career-high 176 2/3 innings. Since the start of the 2021 campaign, the right-hander has been as reliable as they come for Milwaukee, carrying a 3.30 ERA over 738 frames, earning two All-Star selections in the process.

The Brewers continue to trade away their highest-paid players before they hit free agency, recouping young talent in the process and never missing a beat - evidenced by four division titles in the last five years. Expect more of the same this winter in terms of shedding players on expiring contracts. Cubs fans can only hope that, this time around, their stranglehold on the NL Central breaks.

You want to talk about breaking the internet? The already heated Cubs-Brewers rivalry would hit unprecedented heights if Peralta called Wrigley Field home in 2026.

Sandy Alcantara

Sandy Alcantara was one of the biggest names being floated at the trade deadline but, when the dust settled, the former NL Cy Young Award winner stayed put in Miami.

He looked more and more like his old self as the season went on, posting a 3.33 ERA in the second half that was dramatically improved over his 7.22 ERA in 18 first-half starts. If the Marlins shop him this winter, they'll likely find a more receptive market than they did this summer - making him one of the top names to watch this offseason.

Alcantara can be controlled for both the 2026 and 2027 seasons - so the asking price will be sky-high and, if no deal comes together, the Fish can always look to shop him again in July or even next winter. Again, Cubs fans won't love the amount of young talent it would take to pull this trade off, but you don't get something for nothing.

Luis Robert

The Chicago White Sox improved in 2025 - but after posting the worst record in MLB history the year prior, there was only one direction to go. Unfortunately for the South Siders, outfielder Luis Robert was a non-factor for much of the year, making his $20 million team option for 2026 a bitter pill to swallow.

Chris Getz suggested the Sox would pick it up, but whether or not he's with the team come Opening Day remains to be seen. His name has regularly come up in trade rumors in recent years and, while there are better fits in a deal, the Cubs could, at least in theory, swing a deal for Robert to round out the outfield mix.

Before suffering a season-ending hamstring injury, Robert showed signs of life, slashing .298/.352/.456 in 31 second-half games, but his overall body of work left much to be desired and he is now two years removed from his 38-homer 2023 campaign. Injuries have taken their toll and the former All-Star has appeared in more than 110 games just once in his six years in the big leagues.

Assuming Tucker departs - and with the need to bolster the rotation, which could necessitate moving several top prospects - Chicago could acquire Robert and pencil him into right field for '26. A bounceback campaign on the other side of town (not to mention another team option for '27) would breathe new life into a Cubs-Sox rivalry that's gone dormant of late.

Do I think this is particularly likely? No. But it's a fun thought exercise, nonetheless.