Should the Yankees regret trading all those young pitchers?

The Yankees are usually contenders. That itself doesn’t necessarily mean they make a lot of trades (though they do), but it does mean that when they do trade, they’re usually trading prospects or young players for established big leaguers. Name a season, name a trade. There have been a lot of them.

By that process, the Yankees have traded away a lot of young pitchers. Damn near a whole pitching staff’s worth. Given their incredible string of injury luck with regards to pitchers this year, I thought it might be worth a check-in on some of the kids who are pitching in pinstripes in an alternate universe. It’s worth talking about because it’s a little bit remarkable how few of those pitchers have gone on to have impact roles in the majors since being dealt. Trades for Sonny Gray, Joey Gallo, and Frankie Montas have done a number on Brian Cashman’s career hit rate lately, but looking at the performances of some of the players sent the other way makes one think they could still look a lot worse.

Let’s start with Hayden Wesneski, the 2019 sixth rounder who hurled over 200 innings of low-threes ERA ball between Somerset and Scranton/Wilkes-Barre in 2021-22 before going to Chicago last summer in exchange for Scott Effross. The deal made sense, given what the Yankees clearly saw in Effross, but after an excellent cameo with the Cubs at the tail end of 2022 (2.18 ERA, 33 IP) and an equally excellent Grapefruit League performance in March, it looked as if the Yankees might have made a mistake. But despite high expectations, Wesneski has mostly flopped so far this year. While he’s sprinkled in a few gems against some of the worst offenses in baseball – he threw seven one-run innings against Oakland in April, and recorded back-to-back starts doing the same over six innings against Washington and Miami at the beginning of May – he also got blown up for seven runs on two separate occasions, and failed to make it through five innings in another three.

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It hasn’t been all bad, but the 4.92 ERA paints a fair enough picture. When Kyle Hendricks made ready to return from the IL earlier this month, he was optioned to Triple-A, and recalled on Tuesday to pitch out of the bullpen. With Justin Steele leaving yesterday’s start with forearm tightness, it appears Wesneski will once again be getting turns through the rotation, so he’s still got time to turn things around. It’s nonetheless surprising to consider that for everything that’s gone wrong in New York, he’d still only be on the fringes of the rotation.

As miserable as the Montas deal has been for the Yankees, it hasn’t exactly been going well for Oakland, either. Even though “things going well” clearly isn’t what the Oakland front office was trying for this year, they were certainly hoping for something better than the ghastly 5.98 ERA produced to this point by J.P. Sears, Ken Waldichuk, and Luis Medina.

The only positives to be found in that group right now belong to Sears, Oakland’s innings leader, whose 2.94 ERA in the month of May lowered his overall mark to a respectable 4.37. Along with Roansy Contreras (who we’ll get to in a minute), he’s one of the only pitchers in this article who the Yankees might be genuinely missing right now, though he also has the lowest upside of anybody mentioned here. It might be the clearest example of the tug-and-pull of the team’s developmental and transactional philosophy. By stuff and physical talent, Sears is the least impressive of any of these names. Drafted in the 11th round, Sears is the kind of pitcher whose ability is the most easily replaceable for an org like the Yankees. But when things go completely sideways — which is what you can call getting zero innings out of Montas, Carlos Rodón, and (until last week) Luis Severino — he’s the kind of reliable, low-variance pitcher that’s really nice to have waiting in the wings.

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You’d still include him in a trade like last summer’s every time — just maybe perhaps not when you’re already losing another 60 percent of the Triple-A rotation. Waldichuk (7.43 ERA in 49.2 IP) and Medina (6.83 ERA, 27.2 IP) have both been terrible in Oakland, but it’s hard to wonder if they wouldn’t be performing better if they were still in the organization that nursed their breakout. Oakland’s history with pitching is typically quite solid, but both pitchers’ development seems to have completely stalled.

Every prospect report’s fear about Waldichuk’s control has thus far materialized with gusto. His walks have ballooned to 12.5% (over five per nine innings), and the electric stuff just hasn’t missed enough bats, allowing 66 hits and generating just a touch under a strikeout per inning. Medina has dealt with injuries, and while his command issues haven’t manifested in an abnormal number of walks, he simply can’t put the ball in good spots, allowing boatloads of barrels and, like Waldichuk, not getting nearly enough strikeouts to account for it.

Pitching is weird. Evaluating is hard, and developing it is even harder, which can make trading painful. Ezequiel Durán is already making the Joey Gallo trade look even worse than it felt when Gallo was in pinstripes, but there was a moment when some wondered if Glen Otto might wind up being the prize of that deal for the Rangers. Otto was, like Wesneski, a sixth-round pick of the Yankees (2017), and followed a similar developmental and career track. 33 MLB starts, a 5.33 ERA, and Tommy John surgery later, it appears that will not be the case.

Indeed, it is remarkable how little regret there is to be had over the promising young pitchers traded by the Yankees over the last half-decade or so, just by their sheer volume. Taking it back even farther, the James Paxton and Sonny Gray trades brought disappointment of varying degrees (though Paxton had his moments), but how many of you have pined for Justus Sheffield or James Kaprielian since then?

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There may still be time to miss Roansy Contreras, who has a league-average 4.33 ERA in nine starts this year after posting a 3.79 mark in 95 innings as a 22-year-old rookie last season. Armed with a mid-nineties heater and a devastating slider, he still has a lot of work to do before becoming any kind of force, but with a viable curveball and ability to flash a changeup, the complete toolkit is there. Even then, it’s difficult to feel as if it’s production that the Yankees are missing out on. Unlike Gray, Gallo, and Montas, Jameson Taillon more or less did what he was asked in New York, delivering two solid seasons on the mound with a personality that engendered no clash with any bloodthirsty media. Meanwhile, Contreras was a developmental step behind just about everyone else here, having not yet tasted High-A at the time of the deal. There are simply too many more steps there to have envisioned him contributing to this Yankees team in the same way we can Wesneski or Sears.

All in all, it’s a frighteningly low success rate for Cashman’s trade partners. Whatever his flaws are in identifying whether potentially incoming players will be useful for the Yankees, he seems to be adept at identifying which pitchers are keepers and who they’re comfortable seeing elsewhere. When you combine that with a player development operation that gives you plenty of both, there’s little reason to not make the kind of trades he’s made every single time. They may get burned eventually, but the recent results seem to say that the upside to making that big trade splash is almost always worth the cost. Trade on!