5 Impending Free Agents Who Should Shape Cubs' Trade Deadline Plans

[Matthew Trueblood]

We're inside two weeks until the 2024 MLB trade deadline, and the Chicago Cubs need to be sellers during that time. They have a variety of options, though, and choosing which to pursue is a matter of sifting through both internal and external talents with an eye on 2025 and beyond.

Image courtesy of © Thomas Shea-USA TODAY Sports

The particular shape of the Cubs' frustrating first half has closed some doors for Jed Hoyer and company. At the outset of the season, names like Pete Alonso (a free agent at season's end) and Vladimir Guerrero Jr.(a costly potential trade target) were high on the wish lists of many Cubs fans. Now, they should almost be completely eliminated from those fans' thoughts. Michael Busch has been one of the best stories of the team's season, and the team needs to save either first base or DH for him for the foreseeable future.

Since it also doesn't look like Seiya Suzuki is a viable big-league outfielder, defensively; or like Cody Bellinger will be opting out and heading back to free agency; or like Christopher Morel can play third base, it doesn't make sense to wedge an extremely expensive Alonso or Guerrero into the team's plans for the second half of this decade--let alone to give up major young talent, as they would have to do to acquire Guerrero.

Let's talk, then, about the five high-profile players hitting free agency this fall who should occupy fans'minds, and whose impending availability should inform the front office's strategy over the next fortnight.

Juan Soto, RF
While he's only a slightly better positional fit than Alonso or Guerrero (in that he's only marginally better in the field than is Suzuki, and might not be any better, were he tasked with playing the tough sun in right field at Wrigley Field on a regular basis), Soto is a special category. He's one of the four or five best overall hitters in baseball, with those skills heavily weighted toward things (power and plate discipline) that will age exceptionally well and port across a change in environment. He's very nearly as good as Aaron Judge, but is hitting the market a half-decade younger than Judge did.

For all those reasons, Soto is likely to sign for more than half a billion dollars, and therefore, he's overwhelmingly likely to sign somewhere other than the North Side. Still, he belongs to an echelon of talent the Cubs need to start pursuing. They don't develop players of this caliber. They don't draft high enough to get ahold of players this talented through pure scouting. They have to at least take a serious look and make a good-faith offer every time someone like Soto hits free agency. It only happens a few times per decade, anyway.

In the short term, that means clearing a path. With Bellinger likely to be back next year, it becomes more urgent than ever to trade one of Ian Happ and Suzuki, clearing some space in both the payroll and the positional picture for the next few years. Though it already looks like the Cubs are just below the first luxury-tax threshold, it's also crucial to ensure that they stay that way, because their taxpayer status will affect the penalty they pay if they sign a player of Soto's caliber this winter, and signing him would mean being a taxpayer for the next few seasons, at least. You want to be starting from the non-payer level, going into such a deal.

Alex Bregman, 3B
It's clear that Morel isn't the third baseman of the future. Maybe Cam Smith is, but that's a little ways off. Matt Shaw is a fine player with a bright future, but it's more likely to be at second base than at third. His bat might not profile well at the hot corner, and even if it does, his defensive skillset might better align with the demands of the keystone.

Counting either Shaw or Smith as a hatched chicken would, in any case, be the kind of foolish error the Cubs have made too often over the last several years. They have to stop thinking of themselves as an elite player development organization, unless and until they actually become one, so they can operate in a clear-eyed, non-delusional way. One thing that means is ardently pursuing a player like Bregman, who is batting .256/.316/.414 in his age-30 season but will surely finish the season with his metronomic .800+ OPS. Since the start of 2022, his OPS before the All-Star break is under .750, but after the break, it's just a hair shy of .900.

Bregman is an exceptionally tough out, and would be the consistent, high-floor hitter missing from this lineup full of streaky sluggers. He's going to be expensive too, but age and a less obviously elite profile will reduce his asking price a little bit. The Cubs should be in heavily on him, and the move to set that up is obvious: trading Nico Hoerner for the solid young talent he should command, to clear second base for Shaw or Morel, making it possible to land Bregman and slot him into the everyday lineup.

Corbin Burnes, RHP
Illustrating how much work the Cubs have to do, it still feels like the Brewers won the trade they made with the Orioles this winter, even after Burnes started the All-Star Game Tuesday for the American League. Milwaukee got budding star infielder Joey Ortiz, potential long-term bullpen weapon DL Hall, and the 34th overall pick in this week's Draft, with which they selected college bat Blake Burke and were able to further goose a generous bonus pool. They're going to win the 2024 NL Central, and they look very nicely set for 2025 and beyond, too.

That said, Burnes's season is important, because it reaffirms his status as one of the game's best and most durable aces. Craig Counsell knows him, and has gotten the best out of him. His approach mirrors what the Cubs like their pitchers to do, and as the manager gets more chances to shape his staff and filter his preferred messages out to players, that figures to hold true. Burnes will be a candidate to get $300 million on a single deal, as only two other pitchers ever have, but no matter the exact price tag he eventually commands, he's going to be the top pitcher on the market this winter.

Starting pitching has been the strength of this year's Cubs, but maybe it's a strength from which they need to trade, in order to build the best possible club in 2025. With Soto and Bregman the only positional free agents with any meaningful profile who will move the needle for next year's team, maybe the move is to swap Justin Steele, Jameson Taillon, Shota Imanaga, or Javier Assad (whichever turns out to yield the most value in return, based on what the Cubs project each to actually do in the next few years) for a position player-centric package, akin to what the Brewers just did with Burnes--and then splash money around this winter in the deeper pitching market, be that on Burnes himself or on someone like...

Max Fried, LHP
Whereas Burnes is as good a bet to take the ball and work deep into the game every fifth day as any starter in baseball, Fried is a health risk. He doesn't strike out as many hitters as Burnes does, either, and is more vulnerable to the odd blowup start. When he's right, though, he's even more dominant than Burnes. With a deep arsenal and a diverse skill set, he induces ground balls at one of the best rates in the league; limits walks; and keeps the ball in the park. He could be a very simple 1-for-1 replacement for Steele or Imanaga, although a more expensive one. This is one of the ways the Cubs could (by being less risk-averse and more willing to spend like the big-market behemoth they ought to be) attempt a lateral move on the pitching side and get more young positional talent in the process.

Jack Flaherty, RHP
Fried, Burnes, Soto, and Bregman are all going to be given a qualifying offer on their way into the free-agent pool. That means each will cost the Cubs a draft pick, should they manage to sign them. Flaherty, Fried's high-school teammate, is an exception. The Tigers will trade him before the end of this month, and once they do, he'll be ineligible to receive a qualifying offer. Whichever team signs him this winter, all they'll have to give up for him is cash.

It'll be a lot of cash, because Flaherty has made some overdue and vital adjustments this season. In the wake of them, he's striking out over 32% of opposing batters, and walking fewer than 5% of them. If he can sustain the slider command he's shown this season, Flaherty is going to remain an ace, and he has good enough control to pitch deep into games, too.

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The Cubs front office needs to think like a chess player over the coming weeks and months. Each move they make (or don't make) will have short- and long-term ramifications. As they choose from their menu of possible pursuits at the deadline, they have to think about how each would set up another move this fall or winter. It's important that they make some moves, but the risk of making the wrong one is clear and present. These five players should loom over each course they choose, because of the way each could change the organization and reshape their needs.

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[Tryptamine]

With about 99% certainty we can cross Burnes and Soto off the list. This FO has proven they don't swim in the deep end of the talent pool.