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With just a fistful of days left before the MLB trade deadline, the direction and a few constraints are clear. The 2024 Cubs aren't good, and Jed Hoyer has helpfully acknowledged that he won't trade for players who only help this season's team. With a robust farm system and a pressing need to be better next year, though, could they pry loose a star-caliber contributor with significant team control?

Image courtesy of © Andrew Dieb-USA TODAY Sports

That Hoyer and company understand their situation better than to try to make short-term upgrades is encouraging. The next logical question they face, though, is an equally important one: how do you go about acquiring players who represent long-term upgrades, and who can help you avoid the grisly fate of being this forgettable again in 2025? The obvious answer is to be patient, develop what is one of the league's stronger farm systems, and make a splash or two in free agency this winter. But what if the right opportunity is out there right now, rather than later?

The Cubs aren't the only disappointed club looking to build for the future this month, and they're much closer to contention than a few of the others, like the Athletics, Angels, White Sox, and Rockies. (Hey, that almost sounded like a carefully chosen list!) Some of those other teams have great players under team control beyond 2025, who could be part of the Cubs' next winning window--but they also have significant motivation to move those guys now. Waiting until this winter (let alone next summer) might not be an option. So, which guys are good enough to justify paying a high price in young talent right now (even though it includes the cost of their contributions for the balance of 2024, which won't matter), to position the Cubs as a championship-caliber team for the next half-decade?

Luis Robert Jr.
Robert isn't as young as he might feel. He'll turn 27 just after the trade deadline. He's also vulnerable to lots of whiffs, and as he's tried to tone down his aggressiveness and accept some walks this season, he's seen his strikeout rate spike to the north side of 33%. There are also major durability questions, given that last year was the only one of his career in which he's played anything like a full season. Those are the downsides, and they're familiar refrains to most Cubs fans, because Robert plays right across town and the mounting frustration for Sox fans is well-known.

The upsides make up for all that. Robert doesn't hit for power as consistently as you might like or expect, given his tools, but last year was the breakthrough in that regard, as he hit 38 homers and 75 total extra-base hits. When he's been on the field this year, it's been the same story. Built like a strong safety, Robert is going to keep popping plenty of homers, and his speed translates to plenty of stolen bases and some strong defense in center field. He's under contract through 2027, if whichever team controls that contract exercises each of their options, and will only cost $55 million in total over the next three seasons.

Trading with a team with whom you share a city is tough, but we know the Cubs and Sox are capable of it. Hoyer has a farm system strong enough to put together a leading offer for Robert, and few players with any degree of availability are capable of transforming the Cubs lineup the way Robert could.

Garrett Crochet
Speaking of the White Sox, of course, Crochet is making huge headlines. If he weren't on an innings limit for this season, he'd be a very legitimate AL Cy Young Award contender, with power stuff that has translated surprisingly smoothly to starting after an early career spent in the bullpen. The caveat in that sentence looms large for contenders who are interested, though, because his usage limitations will cap his impact on anyone's World Series aspirations for 224.

Though four years Justin Steele's junior, Crochet is actually a year closer to free agency. His fast track to the big leagues and subsequent injury troubles have shaped one of the strangest career arcs in recent memory. He's under team control for just two more seasons after this one, but an acquiring team would be in a decent position to negotiate an extension with him. Even without one, he'd be such a high-impact addition that it's tantalizing.

Brent Rooker
Injuries and the pandemic distorted the early career of Rooker, too, making a player whose profile made him a good candidate to bloom late all along guaranteed to do so. He's bloomed in extraordinary fashion since the start of last season, though, with 30 homers in 2023 and 23 already this year, all playing his home games in Oakland. A take-and-rake pull-side slugger, Rooker could hit 35 or 40 homers in a good year at Wrigley Field. He strikes out a ton, but also draws plenty of walks, and would be the traditional cleanup man the team has needed for at least three years.

Rooker will turn 30 this November, but still has three seasons of team control remaining after this year. He's not likely to be good much longer than that, but the Cubs wouldn't need him to be. They could pay the price to get him, and slot him into their lineup right away, with increased confidence that 2025 will find him anchoring a more powerful offense. He'll get expensive in arbitration after that, but not prohibitively so, and for a team desperately needing pop, he's an obvious target.

Logan O'Hoppe
This is a bit of an out-there idea. O'Hoppe, 24, is under team control four more years after this one, and he's a career .262/.321/.472 hitter. He's a slightly below-average pitch framer but a strong controller of the running game, and his reputation as a game manager and handler of pitching staffs is strong. He's a budding star behind the plate.

Here's the thing: catchers all have short shelf lives, and the Angels aren't very close to contention. Nearly every day brings new evidence that that front office doesn't really know what it's doing. Swooping in and simply stealing a player as good as O'Hoppe isn't possible, but prying him loose from them might be easier than it would be from another organization that was a bit less of a mess.

The prospect package it would take to bring in O'Hoppe would be truly staggering, but the Cubs don't have to pay for him solely with prospects. It's possible they could get involved in a three-way trade in which Justin Steele goes to a high-level contender, and both the Cubs and the team acquiring Steele send prospect talent to the Angels in a huge package. Steele's value to a contender right now might be higher than O'Hoppe's, despite the latter being five years younger and under team and cost control longer. Therefore, the Cubs might get some small secondary piece in the deal, too, without giving up much more than Steele. The Angels have some interesting arms under long-term control, but whom they haven't had success developing yet.

Ryan McMahon
The Rockies sound a bit more like a rational organization, lately, which means
 they might be more open to trading a player like McMahon than they have tended to be in the past. According to one report, they've told McMahon he's not going anywhere, and he did sign a long-term extension with them in 2022, but if they're realistic and ready to be proactive, they have to see that keeping him would be foolish. Left far behind by the rest of their division, they're just now getting better at scouting and player development, in ways that might pay off in half a decade. 

McMahon is only under control through 2027, and will cost $44 million over the final three years of the deal. His timeline doesn't match theirs, and he's not the same face-of-the-franchise star that Troy Tulowitzki, Carlos González, or even Trevor Story were, anyway.

However, McMahon should appeal quite a bit to the Cubs. He's a left-handed hitter with ample power (though more in the form of doubles than over the fence, much of the time), and he's taking walks at an excellent rate this year. He's also one of the best defensive third basemen in baseball. He'd answer a lot of questions about the long-term alignment of the Cubs infield, just as they're pondering creating more such questions by trading Nico Hoerner.

Farm depth like the Cubs' is valuable in two ways. It can yield huge on-field value, directly, by having those players develop into homegrown stars. However, it can also return value by turning into trade value, and bringing back players like these. If the Cubs can consolidate some of their organizational depth this week, create more flexibility, and start to put cornerstones in place for a winning window they hoped would open this year, they'll be in much better position next July than they're in right now.


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Old-Timey Member
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I'd love to do some one-stop shopping and do a monster deal with the A's or Angels.  Something like Rooker and Langeliers or O'Hoppe and Rengifo (and Detmers?).  Roll into the offseason with a to-do list of, pending what goes down with Taillon and Bellinger, one starting caliber player and some relief help.  

Like I don't love Alex Bregman this winter, but if you've got all that added oomf in the lineup from Rooker and Langeliers banked it's a different story.  Filling the one remaining hole in the lineup with one of the premier patience/contact hitters in the sport makes the calculus completely different.

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