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Before swallowing the bitter pill of trading a beloved left-handed starter with a bulldog mindset and an ever-improving track record, the Cubs would have to be convinced that doing so was netting them a transformational talent. There might be a perfect storm brewing, though.

Image courtesy of © David Banks-USA TODAY Sports

After this season, the Cubs will still control the rights of Justin Steele for three more years, assuming they don't trade him first. Steele reached arbitration as a Super Two player last winter, and is making $4 million this season. He's going to get expensive over the next few years, but everything about his performance over the last two calendar years suggests he'll be worth it. Since Jul. 19, 2022, only one pitcher with at least 250 innings pitched has a lower ERA than Steele's 2.70 is impending free agent southpaw Max Fried--and he's at 2.68, in about 45 fewer innings than Steele has thrown.

As discussed yesterday, though, Fried is one of a small but exciting cadre of pitchers set to hit free agency this winter, and since Steele won't be cheap over the course of his arbitration years anyway, maybe it makes more sense to invest in one of those guys--if you can get a player who alters the future of your franchise on the positional side, in the process.

It's very rare that any team will let go of such a player in this cost-conscious, youth-oriented sport, but Steele is the kind of player who compels teams to do so. Three and a half years of team control is a lot, and we're talking about one of the game's best starters. In the heat of a pennant race and having made an unfortunate habit of battling injuries in their starting rotations, three teams stand out as having both the young talent and the motivation to make a big move.

Baltimore Orioles
It's no secret that Baltimore has the deepest, scariest collection of young hitters in baseball. The trick is getting prospect-hugging executive Mike Elias to let go of any of them. He's right to cleave to these types of players, whose value doesn't diminish much until you have a truly embarrassing surfeit, and the Orioles are trying to establish themselves as perennial powers in the AL East, just like the Yankees.

The team is inching toward that spot where they do need to move a young hitter or two, though, if it means capitalizing on the opportunity in front of them and leavening long-term fan engagement by making a deep run in October. They traded from their depth to add Corbin Burnes this winter, but Burnes will be a free agent at season's end, and he's not going to give Baltimore any kind of discount to stay put. A longer-term answer and a complement to Burnes atop the rotation would secure the Orioles' place as the favorites for the junior circuit's pennant, this year and into the future.

Jackson Holliday is probably out of reach, even for a player with long-term control, like Steele. His rude introduction to the big leagues notwithstanding, Holliday is still one of the five or six best prospects in baseball. Not far behind him, though, are slightly less balanced sluggers Coby Mayo and Heston Kjerstad. Mayo is a Christopher Morel-esque third baseman, which is to say that his future is probably in right field or at DH, but unlike Morel, he seems to have an optimized approach and the ability to lift the ball consistently to left field. He could be a perennial 30-homer threat (with 40-bomb upside) in the middle of the Chicago batting order, with an above-average OBP to boot.

Kjerstad is a bit more likely to work as an outfielder in the long run, though he'd be harder to pry away, too, since (unlike Mayo) he has already shown the ability to hammer big-league pitching and is on their big-league roster. He and Mayo are good echoes of the Michael Busch situation from this winter, though: extremely talented players blocked within a great organization, to whom the Cubs might provide the crucial opportunity. The Cubs could only get one of them for Steele, of course, and they'd have to be right about which one, but they'd also land some secondary piece in the trade.

Los Angeles Dodgers
Hey, speaking of the Busch trade, maybe the Cubs could revisit that very well. It's not clear when Yoshinobu Yamamoto will be ready to take the mound again for the Dodgers. Dustin May just had his annual season-ending surgery. Walker Buehler isn't himself anymore, and whenever Clayton Kershaw returns from his own offseason surgery, it might be to make his last ride with the team of whose excellence he's been the biggest symbol for the last 15 years. There are holes in this rotation, and there's a deep hunger in this fan base for a championship in a season that counts. They still haven't won one since 1988.

After signing Will Smith to a 10-year deal (even if it's not really a 10-year deal) this spring, the Dodgers have another prospect with plenty of pedigree who doesn't have a clear path to playing time. Dalton Rushing is batting .266/.377/.459 in the Double-A Texas League, as the team brings him along slowly in the system. Rushing, 23, is a lefty batter and a no-doubt catcher who's not going to have to move to first base or DH. He'd almost certainly be in Triple-A for any other organization, and in many, he'd already be starting at catcher.

Rushing isn't the only enticing player the Dodgers have, either. Josue de Paula is an outfielder who's not even 20 yet, and who has real star potential. As Kevin Alcántara's prospect star dims, de Paula is a player with the same kind of upside that excites so many about Alcántara. The comp illustrates the risk with such a player, but don't lose sight of the reward that comes with that, if the player pans out. The Dodgers also have such an impressive pitching pipeline that rounding out a trade package would be easy and fun. Maybe the Cubs could get Jackson Ferris back.

Minnesota Twins
One of these things is not like the others, right? The Twins are neither a financial behemoth nor a lauded producer of superstar prospects. Yet, they're marching toward what would be their fourth division title in six years (although one was in that season that doesn't count), and quietly, they've become one of the deepest organizations in baseball. They have three different players who could headline various versions of a very intriguing Steele deal.

Walker Jenkins would probably be the toughest to peel away, and he's also the furthest from the majors. For those reasons, maybe he's the least likely or important of the trio. He might also have the highest ceiling, though, with a chance to be a plus-hit, plus-power, plus-glove outfielder who goes to multiple All-Star Games. The funny thing is, Emmanuel Rodriguez has that potential, too. Though just 21 years old, Rodriguez already has 167 plate appearances at Double-A Wichita, and he's batting .298/.479/.621 there. That OBP is not a typo. Rodriguez has 42 walks in that short time, which is typical of him: he's one of the most patient hitters in professional baseball. He also has speed and power, and will stick in center field until he's 30 if he doesn't end up on a team that also has Pete Crow-Armstrong.

Rodriguez is on a rehab assignment in the Complex League right now; injuries have been the only thing capable of slowing his ascent to the majors. He'd be a marvelous headliner in a trade, though. So would Brooks Lee, whom the Cubs could have taken instead of Cade Horton in 2022--but who signed for about $1.2 million more than Horton did, when the Twins took him right after Horton. He's now with the Twins' parent club, and looks like a star-caliber second or third baseman who would be able to plug and play at either spot for the Cubs. The Twins would be loathe to let him go, of course, but with Willi Castro, Carlos Correa, Royce Lewis, José Miranda, and Edouard Julien, they have so much depth across the positions Lee plays that they might surrender Lee for the affordable control and playoff upside of Steele.

Mayo, Kjerstad, Rushing and Rodriguez stand out, especially, as prospects who match proximity, impact potential and attainability, and who could anchor a trade package for Steele that would have to at least get Jed Hoyer talking. As the Cubs make what Hoyer has termed "tough decisions" over the next 12 days, they have to think about whether keeping Steele and paying him handsomely for the next three years is the most sensible course--or whether it would be wiser to add a potentially elite position player with more team control to their mix.


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Posted

It would take a massive haul for me to be on board with this. He's under control up to 2028, and been a top 10-15 pitcher in baseball since the 2nd half of 2023. It would take something that's not going to be offered by anyone like Holliday+Heston Kjerstad+Cade Povich.

Posted

Steele has the best ERA in baseball over the last 2 calendar years (min. 250 IP)

Hoerner is replaceable enough internally that i like gauging the market, but i don't know how we really improve by selling off a steady frontline SP unless maybe it's Basallo & Holliday coming back

Posted

Yeah it'd have to be a HAUL at this point.  Justin Steele wasn't even supposed to be Justin Steele - how'd the Roy Halliday trade turnout.

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