Ranking the Yankees’ top 10 trade deadlines of the past decade


On the heels of an exciting trade deadline, the effects of which can’t yet really be known, memories and feelings of past deadlines have been at the forefront of my head. What better exercise for this moment than to rank the last 10 deadlines for the Yankees?

These rankings will of course be subjective, but I’ll try to weigh each deadline’s impact on the future, and the simple overall entertainment value in running down the list. Let’s get into it.

10. 2020

Key additions: None

Key Departures: David Hale

Due to the COVID-shortened season, 2020 was a weird and largely uneventful deadline for the Yankees, as they just sent David Hale to the Phillies. Beyond that, not much else of note, which at least makes picking the last spot pretty easy for me.

9. 2015

Key additions: Dustin Ackley

Key departures: None

Another fairly uneventful trade deadline for the Bombers, 2015 saw Dustin Ackley’s arrival as the most significant deadline move. He did have a 162 wRC+ in 52 plate appearances, and he was once the second overall pick in the draft, so there’s that!

8. 2019

Key additions: Edwin Encarnación

Key departures: None

The last on this list of largely quiet deadlines, 2019 was such because it was already a very good team. Edwin Encarnación is a big name, which is worth something in this ranking, and he was also solid for the Yanks, hitting 13 home runs and posting a 121 wRC+ in 44 games at the twilight of his career. Of course, they also got him in the middle of June, so while that was helpful in terms of maximizing production, it made the deadline itself a bore.

7. 2014

Key additions: Martín Prado, Chase Headley, Brandon McCarthy, Stephen Drew, Chris Capuano

Key departures: Yangervis Solarte, Peter O’Brien, Kelly Johnson, Vidal Nuño

I wish I could rank this much higher, based on the fantastic list of names that this is, but alas. This team missed the playoffs, though Chase Headley walked off in his debut and was good for the remainder of 2014 (123 wRC+ in 58 games) before sticking around for a few years on a new contract.

Martín Prado did a good job as well in his 37 games in pinstripes; he was flipped to the Marlins in the offseason deal for Nathan Eovaldi. In the first Yankees/Red Sox trade in 17 years, Stephen Drew was bad, but it made me laugh remembering this happened. Brandon McCarthy was excellent, though, with a sub-3 ERA in 14 starts, and he was acquired for just Nuño. We miss Dave Stewart as the D-backs GM.

6. 2022

Key additions: Frankie Montas, Lou Trivino, Andrew Benintendi, Scott Effross, Harrison Bader

Key departures: Jordan Montgomery, Joey Gallo, Ken Waldichuk, JP Sears, Hayden Wesneski

Perhaps it’s unfair to even rank this year, not knowing the impacts of the moves yet, but I think it fits well around the middle of the list for now. Frankie Montas, Lou Trivino, and Scott Effross stand as very important additions to parts of this team that needed reinforcements. The same goes for the outfielders (at least one of them). My confusion around the Jordan Montgomery-Harrison Bader swap holds this year back a bit. And frankly, the whole Joey Gallo thing is just kind of a bummer to me.

5. 2013

Key additions: Alfonso Soriano

Key departures: Corey Black

This may be a bit of a sentimental pick, but this was an extremely fun addition. Although it was really the only one, and it didn’t push the Yankees to the postseason, watching Alfonso Soriano celebrate his return to the Bronx by putting the team on his back for awhile was exhilarating.

Soriano finished with 17 homers and a 131 wRC+ in just 58 games to finish out the year before running out of steam in 2014, while Corey Black never made it to the majors. The only question with this one is if this already-injury-ravaged team of misfits should have sold at the deadline instead, but nonetheless, one can’t deny that Soriano’s slugfest was a blast.

4. 2016

Key additions: Gleyber Torres, Adam Warren, Jackson Frazier, Justus Sheffield, Tyler Clippard, Billy McKinney, Dillon Tate

Key departures: Aroldis Chapman, Andrew Miller, Iván Nova, Carlos Beltrán

2016 was a rare instance of a selling deadline for New York, even if it wasn’t a full-blown rebuild or anything. They tore apart the back of their bullpen, shipping off Aroldis Chapman and Andrew Miller who would eventually meet in the World Series. Carlos Beltrán and Iván Nova were dumped for prospects, too.

They did, however, acquire Gleyber Torres and Jackson Frazier (who went by Clint until recently), who were both extremely high-ranking prospects, and they also scooped up a few future trade chips. Torres is of course the main attraction here, but they restocked their farm system pretty thoroughly in one fell swoop. The only disappointment is that Frazier never managed to pan out in pinstripes.

3. 2021

Key additions: Joey Gallo, Anthony Rizzo, Andrew Heaney, Clay Holmes, Wandy Peralta, Tim Locastro

Key departures: Ezequiel Duran, Josh H. Smith, Glenn Otto, Alexander Vizcaíno, Kevin Alcantara, Luis Cessa, Justin Wilson, Mike Tauchman

Anthony Rizzo was respectable to finish the 2021 season, and of course re-signed in the offseason to become a big part of this year’s team as well. His past month notwithstanding, Clay Holmes has been quite the find, and Joey Gallo seemed like a great idea at the time. Andrew Heaney was … okay, fine, an absolute bust. Still, while there may be some bias at play here and it’s possible that one of the prospects dealt could eventually cause some regret, the current impacts of Rizzo and Holmes play a big role in 2021’s high rating.

2. 2017

Key additions: Todd Frazier, David Robertson, Tommy Kahnle, Sonny Gray, Jaime García, Garrett Cooper

Key departures: James Kaprielian, Blake Rutherford, Jorge Mateo, Ian Clarkin, Tyler Clippard, Dustin Fowler, Rob Refsnyder

Getting three real impact pieces at the deadline doesn’t happen all that often. Frazier, Robertson, and Kahnle were all excellent in 2017, and we ranked the trade to bring the trio in from the White Sox among Brian Cashman’s 25 smartest moves of the past 25 years. The three players played a pivotal role in helping New York come painfully close to a World Series appearance. Although Gray was the big get at the time and he wasn’t terrible in the second half, he struggled mightily the following year. At least none of the young players dealt have become All-Stars or anything like that.

1. 2018

Key additions: J.A. Happ, Zack Britton, Lance Lynn, Luke Voit

Key departures: Brandon Drury, Tyler Austin, Adam Warren, Chasen Shreve, Giovanny Gallegos, Billy McKinney, Dillon Tate

These top two spots are mostly interchangeable to me, both filled with impact major league talent. J.A. Happ and Lance Lynn were excellent, Happ with a sub-3 ERA and Lynn with a sparkling 2.17 FIP in nine starts, though the Yankees chose to re-sign the wrong pitcher in the following offseason. Zack Britton was solid in 2018, and has stuck around to be an important part of the bullpen around injury problems. And Luke Voit was a pleasant surprise, as he stepped in for the injured Greg Bird at first base and hit everything in sight after being dealt. Voit swatted 14 home runs in just 39 games, creeping toward a 200 wRC+, and of course made an impact going forward, particularly in 2020.

Each of these deadlines had their own repercussions, some good and still seen today, some not very impactful at all. The trade deadline always brings excitement, and hopefully this year’s moves will prove to be the best of the bunch when it’s all said and done.



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