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Considering a Cubs blockbuster trade where the Cubs do the selling, not the buying

What would a single trade look like in which the Cubs sent out all of their best trade chips?

Brian Cassella/Chicago Tribune/Tribune News Service via Getty Images

As I wrote a few days ago, it is exceedingly likely that the Cubs front office will ship out anyone of value who doesn’t figure to contribute to the 2024 Cubs and beyond. That article was, well, a bit heavy and not terribly fun.

This one will be much, much different as I focus on the possible outcomes of one question: What if the biggest deal of this trade deadline isn’t the jettisoning of Juan Soto and is, instead, a blockbuster deal by which the Cubs sell of their biggest chips in a pennant-altering whopper? Let’s take a look.

Before looking at specific possible packages, let’s be clear about the basic framework of such a deal. It would involve the Cubs sending out their three biggest trade chips — All-Star catcher and impending free agent Willson Contreras, All-Star left fielder and post-2023 free agent Ian Happ, and impending free agent closer David Robertson — to a club in need of catching, another impact bat, and bullpen help. Thankfully for the Cubs, just about every contender needs an additional switch-hitting, cheap, controllable bat and a cheap late-inning reliever. And plenty of contenders need catching, too.

The potential buyers are below. And before you ask, despite their catchers’ abject failures this year, no, the Cubs aren’t making a blockbuster deal with the Cardinals to propel their rivals to glory.

  1. Houston. The Astros have gotten sub-replacement production from Martin Maldonado and Jason Castro. The pair has struggled so deeply that 24-year-old prospect Korey Lee got called up this month, despite a .297 on-base percentage across Double-A and Triple-A. Lee may be the future, but at 30 games over .500, Houston needs help at catcher now. The firt for Happ is less obvious, but Yuli Gurriel has followed an MVP-caliber 2021 with a nightmarish 2022, posting a sub-replacement line at first base. Perhaps Happ or even Michael Brantley could pick up an oversized glove and give it a shot? Happ is surely athletic enough for the job.
  2. New York Mets. When the Mets gave James McCann $40.6 million over four years, they figured that they had solved their catching issues. Nope. Between injury and ineffectiveness, McCann has been a flop and his replacements — Patrick Mazeika and Tomas Nido — have both been sub-replacement. Stud prospect Francisco Alvarez waits in the wings, but the Mets desperately need a bridge to Alvarez as they battle Atlanta for the NL East title. As for Happ, well, the Mets have tried five different players at DH; all five are sub-replacement this year.
  3. San Diego. The Padres’ time is supposed to be now. Only things aren’t quite working out for the Friars. Jorge Alfaro is enjoying a solid year behind the dish, but it doesn’t take too much examination to realize that his BABIP (.395) and strikeout rate (34.3 percent) suggest that he may turn into a pumpkin. Happ would likely force left fielder Jurickson Profar back to the dirt or take over at first base for Eric Hosmer. Hosmer finally produced in San Diego with a .389/.457/.597 April. Then the calendar flipped, and since May 1, he’s at .241/.301/.329. Per wRC+, Hosmer has been three percent worse than Frank Schwindel.
  4. Minnesota. Something of a dark horse in these sweepstakes, the Twins have gotten solid production from both their catchers and their left fielders. However, their regulars haven’t gotten on base and they have both the Guardians and the White Sox breathing down their necks. With Carlos Correa in the fold for the year and maybe only this year, it could make sense for Minnesota to push their chips into the middle.

With four teams at the bargaining table, let’s examine what deals might look like from these squads.


The Houston system is awfully shallow at this point, but there’s still enough here to make a deal work. Any deal with the Astros has to start with hard-throwing MLB-ready righty Hunter Brown. Brown turns 24 in August and lacks an elite pedigree or control, but he throws 100 with a plus curveball and is ready for a shot at an MLB rotation job. After Brown, our attention turns to lefty outfielder Colin Barber who is showcasing his complete offensive profile at High-A with strong walk and strikeout rates, solid power, and plus hitting. His offensive game profiles in a similar way to Happ’s, though perhaps not for another two years. Next, we figure out that the only thing better than having Christopher Morel is having another Christopher Morel; the next one is named Pedro Leon. The Cuban defector’s development has been tumultuous, but he has a huge arm, runs well, and is putting it all together at Triple-A this year with 12 homers and 31 steals to go with a robust 14.4 percent walk rate. Finally, a low-minors projectable arm like recent fourth-round-pick Chayce McDermott gives that Cubs one last arm on which to dream.

The Deal: Contreras, Happ, and Robertson for Brown, Barber, Leon, and McDermott

New York Mets

There’s no Pete Crow-Armstrong to acquire this year. Alvarez is off limits, but other meaningful prospects could be had. Stud third baseman Brett Baty could be the headliner that entices the Cubs to package their top chips, but the Mets could balk at dealing him even in such a large move. Baty has it all: power, walks, hitting, and an on-the-dirt defensive profile with a sweet lefty swing. Hefty switch-hitting shortstop Ronny Mauricio is much less attractive than Baty, but he is nonetheless intriguing. Mauricio hasn’t learned to walk (4 percent walk rate at Double-A this year) but he is a 6-foot-3 shortstop with plus power and the handles to stay up the middle. He’s also only 21, so there could be a regular here. I’m more interested in Dominican outfielder Alex Ramirez. Ramirez has a bit of power and some speed showing up in games and earned a promotion to High-A at just 19. He’ll need a couple of years to season and for his body to fill out, but the thought of him patrolling right field next to PCA sure is tantalizing. Righty Matt Allan is a perfect target for the Cubs. A top-20 prospect in the 2019 draft, Allan slipped to the fourth round and commanded a $2.5 million bonus to sign, then underwent Tommy John surgery in May 2021. As a result, he may not throw in a professional game from 2020-22 due to COVID and injury. Still, there’s a top-level starter in there. The Cubs can afford to wait a few years for Allan to develop. Undersized righty Calvin Ziegler present an intriguing relief profile with a huge arm but inconsistent stuff currently yielding big strikeouts and walks in A ball.

If the Cubs want to make things really interesting, they could consider taking back McCann...

The Deal: Contreras, Happ, and Robertson for Baty, Allan, and Ziegler


Contreras, Happ, and Robertson for Mauricio, Ramirez, Allan, and Ziegler


Contreras, Happ, and Robertson for McCann, Baty, Ramirez, Allan, and Ziegler

San Diego

The Padres have a few different machinations that could work given the presence of two headliners in their system even after setting aside shortstop C.J. Abrams given that Abrams is currently filling an everyday role for the big league Padres. Catcher Luis Campusano has the look of an everyday catcher moving ahead, but his timing is tricky; he’s clearly done with Triple-A yet his bat hasn’t showed up yet in the Majors. He may need time to work through struggles that San Diego can’t give him. As much value as Campusano carries, however, this section is primarily here to be a Robert Hassell III appreciation post. Hassell is obliterating High-A pitching with a Bryce Harper-style load-and-swing, peppering the opposite field. He’s plenty athletic such that he could hack centerfield and be dramatically overqualified defensively in a corner; an outfield consisting of Davis-PCA-Hassell would cover an absurd amount of ground. I’m drooling.

San Diego’s system has way more than enough depth to fill out a deal. Ever wondered what Adam Dunn would look like with plus speed? Here’s James Wood at 6-foot-4, 240 pounds, with plus speed. Prefer contact-oriented shortstops with first-round pedigrees? Here’s Jackson Merrill. Want a teen lefty with a sweet swing? Samuel Zavala is here. There are plenty of permutations.

But what about a bigger, messier deal? What happens if San Diego wants to minimize their tax hit in acquiring three Major League vets? Let’s fold in Eric Hosmer. Hosmer is owed $39 million over the next three years on a team with World Series aspirations, yet he’s a sub-replacement level player with 10-and-5 rights following the 2022 season. If San Diego wants to get out from his deal as they attempt to keep Joe Musgrove, the time is now.

The Padres get bonus points for having so many players in the lower minors with monster ceilings, the exact players that the Cubs should be targeting based on their system strength.

The Deals: Contreras, Happ, and Robertson for Hassell, Wood, and Zavala


Contreras, Happ, and Robertson for Hosmer, Campusano, Hassell, Wood, Merrill, and Zavala


I didn’t know which teams made the most sense for such a blockbuster at the beginning of this exercise, but I’m gravitating toward Minnesota. Austin Martin looks very much like Nick Madrigal plus walks, which is to say that his lack of power and defensive value places incredible stress on his immense on-base skills. Martin has only played at Double-A as a professional, and despite hitting .261 with six homers, he has a .399 on-base percentage. If his power or defense kicks up, he’s a plus starter; if not, he’s a risky one-of-a-kind type of prospect.

I’m intrigued by big righty Josh Winder. He forced his way into Minnesota’s rotation this year, features a diverse set of pitches, and comes with a typical starter’s build. He’s on the injured list with a shoulder issue right now, something that could entice the Twins to part with him given that he’ll be missing time as they make their push this season.

The rest of the system features tons of depth pieces in making a deal, such as shortstop Noah Miller (light on power right now, everything else is there), twice-traded righty Simeon Woods-Richardson (enjoying a solid rebound year at Double-A but on the injured list), and designated hitting prospect Matt Wallner (huge power, OK hitter, terrible defender). But any deal with the Twins likely hinges on whether the Cubs love, like, or ignore Martin.

The Deal: Contreras, Happ, and Robertson for Martin, Winder, Miller, and Wallner

The Verdict

The incentives are hard to ignore here. San Diego isn’t winning the West, so they’re heading for a Wild Card series. Houston isn’t getting caugh by Seattle or anyone else, and they’re 12 games clear of the Twins in looking for a first-round bye. Neither club has a huge incentive to make a massive deal. Conversely, a couple of additional wins hold tremendous marginal value for the Mets and the Twins given their tight positions in the standings. Although I like the Padres system the best out of these four clubs, the Mets find themselves in the greatest need of a couple of big upgrades. Thus, while it pains me to say it...

Who’s ready for another deadline deal with the Mets?


Which of the proposed trades mentioned above would be best for the Cubs?

This poll is closed

  • 8%
    (59 votes)
  • 13%
    NY Mets 1
    (91 votes)
  • 3%
    NY Mets 2
    (26 votes)
  • 14%
    NY Mets 3
    (99 votes)
  • 15%
    San Diego 1
    (104 votes)
  • 39%
    San Diego 2
    (265 votes)
  • 4%
    (33 votes)
677 votes total Vote Now