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What trades from the last five years might the Yankees want back?

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The Bombers have avoided any catastrophes in recent years, but they’d probably reconsider a couple of deals

Miami Marlins v New York Mets Photo by Jim McIsaac/Getty Images

“Two roads diverged in a yellow wood,
And sorry I could not travel both
And be one traveler, long I stood
And looked down one as far as I could
To where it bent in the undergrowth…”

That’s the opening stanza of Robert Frost’s iconic 1916 poem “The Road Not Taken,” a meditation on how people make decisions, how we agonize over the unfulfilled possibilities of each rejected option, how we analyze and dissect, ponder and muse, regret and lament, and – ultimately – rationalize our choices to ourselves.

He was undoubtedly talking about baseball trades.

Over the last five years, the New York Yankees have made more than 50 trades, and while they’ve certainly avoided any Christian Yelich-to-Milwaukee catastrophes, perhaps there are one or two moves they’d like a mulligan on.

Now, before we dive into the deals that might qualify, I’ll say there won’t be any Giancarlo Stanton takes in this article, which will focus on who the Yankees gave up and those players’ potential value for the 2020 team, not on how many years and dollars are left on the former MVP’s contract.

Yankees trade Zack Littell and Dietrich Enns to the Minnesota Twins for Jaime Garcia – July 30, 2017

Divisional Series - Minnesota Twins v New York Yankees - Game One Photo by Brace Hemmelgarn/Minnesota Twins/Getty Images

Leading up to the 2017 trade deadline, the Yankees needed an arm. Michael Pineda went under the knife for Tommy John surgery on July 18 and the Bombers – on the back of a historic rookie campaign from Aaron Judge – deserved reinforcements as they entered a stretch run that would see them qualify for the wild card game against these very same Twins.

The reasoning was sound. Garcia, 30, was an established, if unexciting, lefty. Littell was a 21-year-old righty starter with a big 6’4’’ frame who had just been acquired from the Mariners the previous offseason and was putting up some promising numbers across High-A Tampa and Double-A Trenton. The Yankees gave up potential for certainty.

Unfortunately, Garcia struggled to meet even meager expectations in pinstripes, pitching to a 4.82 ERA (4.87 FIP) with an ugly 1.63 WHIP in 37.1 innings down the stretch. He made a lone postseason appearance for the team, tossing 2.2 scoreless innings in a Game One ALDS loss against the Cleveland Indians. He didn’t make the Wild Card roster against the Twins and didn’t feature against the Houston Astros in the ALCS.

Littell has had two big-league stints since the trade, most recently tossing 37 relief innings for the Twins last season; he pitched to 2.68 ERA (3.62 FIP) and 1.16 WHIP. Would he be an intriguing depth option for the 2020 Yankees bullpen? Probably.

Yankees trade James Kaprielian, Jorge Mateo and Dustin Fowler to the Oakland A’s for Sonny Gray and international bonus slot money – July 31, 2017

Oakland Athletics Workout

The overwhelming factor in determining the value of this particular trade – made just one day after the Garcia deal mentioned above – is the mountain of frustration that was Sonny Gray’s time in the Bronx. It just never materialized for Gray with the Yankees and after a disappointing year-and-a-half, he was dealt away in 2019 to the Cincinnati Reds, where he had the nerve to pitch like an ace.

All the Yanks have to show for the Sonny Gray experiment is Josh Stowers, who came over from Seattle in what was essentially a three-team deal. The 22-year-old outfield prospect (about to turn 23 in a few weeks) has a solid minor league track record but lacks huge upside, as this prospect profile lays out.

What makes this an interesting trade to reconsider is Jorge Mateo, once considered one of the Yankees’ most exciting prospects. After several years floundering in the minors, the enigmatic shortstop came alive in 2019, slashing .289/.330/.504 for Triple-A Las Vegas, with 19 home runs and 24 stolen bases in 532 at-bats. Are there caveats? Yes. He was repeating the level and playing in the notoriously hitter-friendly Pacific Coast League. He has also struggled mightily in back-to-back seasons in the Dominican Winter League. We’ll soon see just how much of his flashy potential remains, as Mateo is out of minor league options and a good bet to make a major league roster this season, whether with the A’s or elsewhere.

Would the Yankees, with an open competition this spring for a backup middle infielder, give up Stowers for Mateo, a lottery ticket arm in the oft-injured James Kaprielian and a depth outfielder in Dustin Fowler? Surely they would.

Yankees trade Nick Solak and Taylor Widener for Brandon Drury – Feb. 20, 2018

New York Yankees v Texas Rangers Photo by Ronald Martinez/Getty Images

This was a complicated one – seven players moved between three teams (the Rays and Diamondbacks being the other two involved) – but the principals to consider for this exercise are infielders Nick Solak and Brandon Drury.

At the time, the Yankees were looking at rookies Gleyber Torres and Miguel Andujar manning second base and third base, respectively. Apparently uneasy with such young players in key positions, Brian Cashman brought in an established infielder in Drury, who had experience at both positions. (Neil Walker was also a late signing to bolster the team’s infield depth.) Thankfully, the cream rose to the top. Andujar, defensive issues notwithstanding, and Torres became mainstays in the lineup, finishing second and third in Rookie of the Year voting, respectively. Drury, plagued by migraines, played in just 18 games for the Yankees before eventually being traded to the Blue Jays in a deal that returned J.A. Happ.

Solak was actually traded again, from the Rays to the Rangers in 2019, but he showed a lively bat, slashing .293/.393/.491, good for a 124 OPS+ across 135 plate appearances. He spent time at both second base and third base, but appears defensively limited. Roughly half of his plate appearances came at DH.

His defensive issues would probably have limited his potential on this 2020 Yankees roster, but he’ll be an intriguing bat to watch develop, and perhaps wistfully pine for.

Yankees trade Caleb Smith and Garrett Cooper to the Marlins for Mike King and international bonus slot money – Nov. 20, 2017

Miami Marlins v Arizona Diamondbacks Photo by Jennifer Stewart/Getty Images

If we were assessing this deal after the first three months of last season, boy would it sting!

First, some background: The international bonus slot money was a crucial factor because, at the time, the Yankees were hoping to entice two-way Japanese star Shohei Ohtani to make New York his home. As they would soon find out, though, he only had eyes for the West Coast and eventually signed with the Angels.

That was a bummer!

What was even more of a bummer was watching the lefty starter Caleb Smith post a 3.50 ERA and 1.01 WHIP through the first half of 2019 for Miami. And the righty-swinging first baseman Garrett Cooper slash .306/.375/.473 over the same period. Neither could maintain their impressive paces, however, with Smith finishing with a 4.52 ERA (5.11 FIP) in 153.1 innings pitched and Cooper ending with a .268/.334/.434 slash line with 14 home runs in 414 plate appearances.

However, both are still viable major leaguers while the 24-year-old Mike King hopes to rebound from an injury-plagued 2019. King still has potential, to be sure, and could make his major league debut this season, depending on the health of the starting rotation. Maybe he’ll be the best of the bunch. But thus far, the Smith/Cooper side of the equation has the edge.

Those are the deals to ponder. Which “road not taken” would you like to meander down?