The Yankees’ recent track record with trading prospects

As 2021 progresses, it is likely that the Yankees will start dealing. Cashing in trade chips could reinforce a roster chasing its first World Series title since 2009 after recent painful playoff eliminations. Upon reflection, it anecdotally occurred to me that the Yankees have done well recently at not trading away prospects who make them regret it.

Luckily for New York, and for fan sanity, looking at recent deals confirms my earlier thesis. Cashman rarely trades prospects who then succeed elsewhere, regardless of whether the Yankees “win” each trade.

But ye gods, the Yankees trade frequently. Accordingly, I limited my scope. I began with the acquisition of Didi Gregorius and ended with the James Paxton trade. Transactions since the latter need more time before we judge them.

There are deals in between that I omitted. I ignored the trade that dealt Manny Bañuelos to Atlanta. A former top prospect, his star had faded before his departure. Likewise, I left out the heist that acquired Luke Voit from the Cardinals, as Giovanny Gallegos was not a prominent prospect. Finally, I disregarded the trade that brought Luis Gil to New York. Jake Cave was not a top prospect when Cashman dealt him.

Without further ado ... some recent deals involving Yankees prospects. In December 2014, the Yankees sent pitcher Shane Greene to Detroit in a three-team deal that brought Sir Didi to New York. Classifying Greene as a “top prospect” at the time is admittedly a stretch. He had just completed his rookie season at age 25, though, and gave the Yankees nearly 80 quality innings in 2014.

This swap kicked off a stretch of (mostly) successful trades, though … and it allows me to remind us of Didi’s knack for clutch — and swaggy — dingers. Verdict: Yankees win the trade. Fans have no reason to regret dealing Greene.

A year later, the Cincinnati Reds looked to unload closer Aroldis Chapman, embroiled in domestic violence allegations. Those off-field issues almost certainly affected his trade value. Cashman swooped in.

The Yankees’ 2013 first-round pick Eric Jagielo (10th on PSA’s pre-2015 Yankees Top 20 prospects) headlined the package that went to Cincinnati for Chapman. Famously, Cashman then dealt the closer to the Cubs at the 2016 trade deadline, bringing Gleyber Torres to the Bronx.

None of the prospects Cashman sent to Cincinnati are currently with an MLB organization, and Chapman … well, Chapman’s still throwing smoke. Verdict: Yankees win this trade running away. No reason to rue “what could have been.”

As the trade deadline approached in a scintillating 2017 season, Cashman struck again – sending prospects and Tyler Clippard to the White Sox for relievers David Robertson and Tommy Kahnle, and third baseman Todd Frazier.

This time it was the team’s 2016 first-round pick Blake Rutherford that headlined the package Chicago received. Rutherford remains in the Sox system and is playing well at Triple-A. Neither of the other two pieces in the trade have made the majors.

The trade paid dividends for the Yankees. D-Rob’s second Yankees stint extended through 2018 and yielded 2.5 fWAR. The Toddfather played well down the stretch in 2017 and put up a 115 wRC+ in 66 games. And Tommy Kahnle turned out to be a revelation for the Yankees. He was admittedly subpar in 2018, but that was a valley in between two great seasons in 2017 and 2019. Kahnle compiled 1.9 fWAR in 90 innings over those two seasons, striking out 124 batters.

None of the players the Yankees acquired remain, and it’s theoretically possible the prospects sent to Chicago could bloom. The verdict now, however, is a Yankees win and another where Yankees fans have no reason to curse the fickle fates.

Cashman kept dealing in 2017, acquiring starting pitcher Sonny Gray from Oakland at the deadline. The price? Three of the Yankees’ most prominent prospects — though injury and underperformance affected their stock.

Oakland received 2015 first-round pick James Kaprielian (sixth on the PSA 2017 Top-20), shortstop Jorge Mateo (fourth), and outfielder Dustin Fowler (13th). Of them, only Kaprielian remains with Oakland. Mateo debuted with San Diego last season, and though Fowler has reached the majors, he currently toils for the Pirates at Triple-A.

Thus far, this trade has disappointed both teams. Kaprielian, though, could swing it firmly towards Oakland. He has overcome myriad injuries to make the A’s rotation. In three starts so far in 2021, he has pitched to a 1.53 ERA in 17.2 innings. It won’t take many more quality outings for Kaprielian to win this for Oakland. Verdict: The trade? Push … for now. Regrets? There’s potential, if Kaprielian continues his hot start.

During the 2017 off-season, the Miami Marlins’ most recent fire sale, the Yankees obtained Giancarlo Stanton for Starlin Castro and prospects José Devers and Jorge Guzmán. Both prospects have reached Miami, but their performances are too incomplete to make any definitive judgements. Stanton, meanwhile, has been excellent for the Yankees when he has been healthy, which admittedly has been all too rarely. Verdict: Yankees win the trade, and it looks like fans won’t bemoan the loss of Devers or Guzmán.

Cashman also dealt at the 2018 deadline. He sent a package headlined by pitcher Dillon Tate, once 11th on MLB’s Yankees prospect watch, to Baltimore for relief ace Zack Britton. Britton remains in pinstripes, and though he is currently injured, he has pitched well in the Bronx, with 1.5 fWAR in 105.1 innings since his arrival.

The prospects Baltimore acquired remain in their organization, with Tate the most successful. In three seasons, he has pitched to, or slightly above, replacement level for Baltimore in each. Verdict: Yankees win the intra-division trade and none of the prospects traded away fill fans’ hearts with angst.

James Kaprielian might not be the only former prospect who makes Yankees fans sad. In November 2018, New York acquired James Paxton from Seattle. In return, the M’s received a return built around top prospect Justus Sheffield (28th on MLB Pipeline’s Top 100 prospects in mid-2018).

Paxton was excellent in 2018, racking up 15 wins and 3.5 fWAR in 150.2 innings. Unfortunately, his career-long struggle with injuries caught up to him, and he only pitched 20.1 more innings as a Yankee.

Erik Swanson, one of the prospects Seattle acquired, has pitched well out of their ‘pen in 2021. Sheffield, though, has the potential to make Yankees fans regret his loss. It just depends on which version of him becomes the most consistent. Will he develop into the number two or three starter that he looked like in 2020? Or will he pitch like the Quad-A fill-in that he’s been in his other two seasons for Seattle? He’s still only 25-years-old, so he’s got time to figure it out. Verdict: Trade? Not bad but no room to improve for New York. Regrets? None at the moment, but wait and see.

Recent serious injuries, notably to Corey Kluber, Luke Voit, and Aaron Hicks, increasingly make me think the Yankees will use prospects to pursue reinforcements. The good news, though, is that the Yankees seem adept at self-scouting. Very rarely over the past several years have prospects traded away given the Yankees or their fans reason to regret dealing them. They just have to work on getting more consistency out of the players they get back in return.