Yankees trade deadline preview: New York’s biggest needs, targets and trade chips

As expected, the New York Yankees are on the short list of the best teams in baseball this season. They’ve lost several key players to injury (Zack Britton, Aaron Judge, DJ LeMahieu, Giancarlo Stanton, Gleyber Torres, etc.) and they still have one of the best records in baseball, just like 2019. The Yankees are very good and very deep. Their Plan Bs are as good as many teams’ Plan A.

Yankees GM Brian Cashman has been quite active at the trade deadline in recent years. Since returning to prominence in 2017, the Yankees have added the likes of Britton, Edwin Encarnacion, Todd Frazier, Sonny Gray, Tommy Kahnle, Lance Lynn, David Robertson, and others in the days leading up to the deadline. When the Yankees have a weakness, Cashman acts.

This will be an unusual trade deadline — will it busy because so many teams are in the expanded postseason race, or will it be slow because no one wants to give up prospects or take on money after the shutdown? — but the Yankees, as a World Series contender, figure to seek upgrades aggressively. Let’s preview the trade deadline for Cashman and the Yankees.

Biggest needs

GM Brian Cashman has been aggressive at the trade deadline in recent years.

On the position player side, the Yankees are mostly set even with LeMahieu, Stanton, and Torres expected to be sidelined another few weeks. They have quality replacements in Miguel Andujar, Mike Ford, and Clint Frazier. Offensively, the Yankees need a few of their regulars to start hitting (i.e. Gary Sanchez) more than they need a trade deadline addition.

New York’s needs lie on the mound because Kahnle and Luis Severino are done for the year with Tommy John surgery. J.A. Happ has mostly struggled and James Paxtonwho was missing close to 4 mph, is now on the injured list with a flexor problem. Gerrit Cole, Jordan Montgomery, and Masahiro Tanaka are a fine top three. There’s room for a better No. 4 starter though.

The Yankees value a deep bullpen and I expect them to look for another reliever in addition to a starter at the deadline. Someone to replace Kahnle as a fourth setup option alongside Chad Green, Adam Ottavino, and eventually Britton. That will be their focus prior to Aug. 31, a starter and a reliever. A better backup catcher than Erik Kratz and Kyle Higashioka is lower on the shopping list. 

Possible targets

It has been a brutal season for Matthew Boyd, whose strikeouts are way down and home runs (and, thus, ERA) are way up. The Yankees and Tigers discussed Boyd last trade deadline but talks went nowhere because Detroit asked for Gleyber Torres. The price has presumably dropped and you don’t have to try too hard to see Boyd as a bounce-back candidate. The Yankees value high spin rates and he has a history of them, and Boyd will remain under team control through 2022 as an arbitration-eligible player, which is an obvious plus with Paxton and Tanaka becoming free agents this winter (and Severino not expected back until midseason 2021).

Johnny Cueto is the bigger name in San Francisco but his contract, specifically the $21 million he is owed in 2021, will be a major obstacle during trade talks. It would behoove the rebuilding Giants to eat money to facilitate a trade. As for Gausman, the Yankees know him well from his time in the AL East with the Orioles, and San Francisco has helped him post a career best strikeout rate in the early going thanks to an improved pitch mix (fewer sliders and more splitters). Gausman is a rental and has experience pitching out of the bullpen, so if Paxton returns before October, there’s still a way for Gausman to contribute significantly.


Ken Giles

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After battling elbow woes much of last year, Ken Giles landed on the injured list with a flexor strain three days into this season, so that’s an obvious red flag. He did resume playing catch recently but it is unlikely he will pitch in a game before the deadline. Giles is an impending free agent and his situation is very similar to Josh Donaldson’s in 2018. The Blue Jays kept hoping Donaldson would get healthy in 2018, and when he didn’t, they traded him for whatever they could get (Julian Merryweather, who was rehabbing from Tommy John surgery at the time) rather than potentially lose him for nothing as a free agent. They may do the same with Giles. The Yankees and Blue Jays made “significant progress” on a Giles trade prior to last year’s deadline, according to The Athletic’s Ken Rosenthal. The two sides could reengage with New York getting Giles at an extreme discount, and hoping he stays healthy and has an impact down the stretch and in October.

In addition to Giles, the Yankees also pursued Orioles reliever Mychal Givens at the trade deadline last year, reports Joel Sherman of the New York Post. Giles absolutely dominates right-handed hitters with a hard fastball and sweepy slider from a low arm slot, and that would have definite value in a short postseason series against the fellow American League powerhouses like the Astros (Jose Altuve, Alex Bregman, Carlos Correa, George Springer), Athletics (Mark Canha, Matt Chapman, Marcus Semien), and Twins (Donaldson, Byron Buxton, Nelson Cruz, Miguel Sano). Givens is not a rental — he will remain under team control as an arbitration-eligible player in 2021 — and the Britton deal shows the Yankees and O’s are not against intradivision trades. Alex Cobb is healthy and productive again and could interest the Yankees as well, though he’s owed $15 million in 2021, and that may be a problem.

There may be no reliever more coveted at the deadline than Royals closer Trevor Rosenthal. He walked 26 batters in 15 1/3 innings with the Nationals and Tigers last season, his first year back from Tommy John surgery, and generally looked lost. Rosenthal even spent a little time with the Yankees’ Triple-A affiliate in August, but it didn’t go well (four runs on three walks and a hit batsman in one-third of an inning). This year Rosenthal is throwing as well as he did during his Cardinals days, and he’s throwing more pitches in the zone. This tells a story:

  • 2016: 57.5 percent zone rate
  • 2017: 54.9 percent
  • 2018: Out with Tommy John surgery
  • 2019: 48.4 percent
  • 2020: 56.0 percent

Control is often the last thing to return following elbow reconstruction and now that Rosenthal is a year removed from surgery, he’s looking more like himself. Rosenthal is on a one-year contract and the Royals are out of the race, so he is a Grade-A piece of trade bait. The Yankees have some history with him (last year’s brief Triple-A stint). The question is whether they’re willing to go all-out to win a deadline bidding war to get him.

As our R.J. Anderson recently noted, the Marlins came close to trading Jordan Yamamoto over the winter, and they could rekindle those efforts at the deadline given their young pitching depth. Yamamoto is missing 2-3 mph off his fastball this year, but he is only 24 and he is under team control through at least 2025, plus he has a five-pitch arsenal. He’s a good change of scenery candidate and a potential cheap long-term addition for any team looking for rotation help, including the Yankees. It’s worth noting Marlins director of player development Gary Denbo used to run New York’s farm system, so he’s familiar with many of their prospects. That could help facilitate a trade.

Other potential targets: RHP Keone Kela, Pirates; LHP Robbie Ray, Diamondbacks; RHP Richard Rodriguez, Pirates; LHP Drew Smyly, Giants; RHP Taijuan Walker, Mariners

Trade chips

The Yankees have two talented young hitters to peddle in Andujar and Frazier. Andujar was the Rookie of the Year runner-up two years ago but missed most of 2019 with shoulder surgery and is now stuck behind Gio Urshela at third base. Frazier always hits when called upon but is blocked in the outfield by Judge, Stanton, Brett Gardner, Aaron Hicks, and Mike Tauchman.

New York has resisted moving Andujar and Frazier in the past — the Padres were said to have interest in Andujar two years ago and the D-Backs wanted Frazier in Robbie Ray trade talks last year — and they don’t have to trade them now. They have minor-league options and can be (and have been at times) stashed at the alternate site until needed. Retaining depth is never a bad idea.

The Yankees have the 18th-best farm system in the game according to Baseball America‘s midseason update. Their top prospect, 17-year-old wunderkind Jasson Dominguez, is presumably off-limits in trade talks. Pitchers Deivi Garcia and Clarke Schmidt are top-100 prospects on the cusp of the big leagues. The Yankees may be willing to trade one. I’d bet against them dealing both.

Only players included in a team’s 60-man player pool can be traded this year and the Yankees have eight of their top 15 prospects according to MLB.com at the alternate site: Schmidt (No. 2), Garcia (No. 3), Luis Gil (No. 5), Estevan Florial (No. 7), Alexander Vizcaino (No. 8), Luis Medina (No. 11), Albert Abreu (No. 12), and Miguel Yajure (No. 15). That presumably makes them available.

Teams can get around the 60-man player pool rule with players to be named later. They can include a player to be named in a trade as a placeholder, then, once the season ends, a non-60-man player becomes the player to be named. So, really, anyone in the system can be traded, and New York’s list of untouchables is likely small with their World Series window as open as it’s going to get.

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