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Yankees Trade Deadline Cheat Sheet

Joey Gallo has been such a disaster that Yankees fans have abandoned ridicule in favor of pity. Thirty-six year-old Josh Donaldson has struggled with velocity in the unfortunate reality we never truly considered. A lion’s share of the bullpen expenditures have produced zero or less (I’m looking at you Chapman) production. But we were on a 120-win pace, and a little turbulence is an afterthought if your flight is headed to Barbados.

Lately, however, the destination for the 2022 Yankees has looked less certain. The team’s shortcomings have finally led to ticks in the loss column, which can both be a gift and a curse. Sure they have work to do, but also tremendous clarity. They are looking for (1) a reliable Game 2 starter, (2) an outfielder, preferably one that handles right-handed pitching, and (3) bullpen depth. Let’s look a bit closer at some of their options in hopes of gaining some clarity on the blueprint of the Yankee front office.

Note: If you’d like more information on which Yankee prospects you can expect to see in deals check out Kevin Wisla’s piece here.


The Starters

RHP Luis Castillo

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The Yankees and Reds have had intermittent discussions regarding Castillo over the past few years, now approaching a dramatic conclusion. Castillo doesn’t possess the high-end chase or whiff rates the Yankees tend to prioritize in their arms but it doesn’t seem to be deterring their pursuit. The Yankees’ affinity for Castillo, roster fit, and timing have all but ensured the Reds ace’s new threads, right? The only concern is value. Castillo is the clear cut ace of the market and will thus demand a top-of-the-market package. Do the Yankees see more of a true 1B to Gerrit Cole or an inconsistent, albeit at times brilliant, upper-mid rotation arm? My money is on the former, making Castillo the Yanks most likely big splash.

RHP Frankie Montas

While the focus is on Castillo, Montas very well may end up being the steal of the deadline. He recently missed some time with shoulder inflammation which leads to some uncertainty. If teams are satisfied with the medicals however, he becomes an interesting discount option. He gets barreled up more than Castillo but has him bested in both K% and BB%. Familiarity is important come the deadline and these teams have worked together recently with the Sonny Gray deal and Matt Olson discussions. Castillo is likely still the priority but if Cashman and company are also looking to add elsewhere, Montas makes sense.

LHP Jose Quintana

As previously mentioned familiarity is key this time of year and in this case it exists at both the team and player level. The Yankees and Pirates have worked out a number of deals in recent years including the trades for Clay Holmes and Jameson Taillon, and more recently have discussed Bryan Reynolds, which we’ll get to later. In addition Quintana spent some time in the Yankees system in the early 2010’s and the human element can never fully be discounted. A move for Quintana could pair with Castillo or Montas as affordable depth or be in response to a big splash in another area.

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Other options: Pablo Lopez, Carlos Rodon, Tyler Mahle, Tarik Skubal, Merrill Kelly, Kyle Freeland


The Outfielders:

RF Juan Soto

The only fun way to start here is with the closest Ted Williams comparison we have ever seen. For those uninformed, Soto has historic plate discipline as well as elite power for a 23 year-old. Acquiring a player of this caliber for 2 ½ seasons is unprecedented and will lead to a historic haul for Nats president Mike Rizzo. Are the Yankees willing to meet that price? They are thin on pre-arbitration players on the big-league roster and have a strong, yet unspectacular, farm system. They have #1 prospect Anthony Volpe penciled in at shortstop as soon as 2023 and he would be the centerpiece, yet only a portion, of the deal. Will the Yankees desolate the farm for a Soto rental, or worse as a Judge replacement? Based on the Yankees’ moves in recent years, the answer is likely no. However, the Yankees interest in Soto is seen as legitimate and no one would dare underestimate the Yankees’ financial muscle. If there was ever an all-in, league-altering move to make, this is it. 

CF Bryan Reynolds

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While the odds on Soto remain slim, the Yankees have stayed engaged with Pittsburgh on Reynolds. The switch-hitting center fielder would give the Yankees stability in their outfield through 2025. He hasn’t matched his 2021 output thus far in 2022 but a recent surge has done enough to impress those in the Yankee organization. His barrels are down, whiffs are up, and chase rate has risen as well. Is Reynolds the perennial All-Star that the Pirates are charging for? I don’t expect him to be moved, but if that changes, expect the Yankees to be at the top of the list.

LF Andrew Benintendi

Sure, I could’ve picked David Peralta or Ian Happ for this piece but Benintendi has been the name most often linked to New York, and is probably the best fit. Benintendi has altered his swing and approach a bit since his Boston days, which will negatively impact the lefty short porch advantage he’d stand to enjoy. His pull rate is at a career low and his fly ball rate is its lowest since 2017. On the plus side his strikeout rate is in the elite category and his low chase rate has added up to a sterling .389 OBP. His .368 BAbip is unsustainable but not outrageous, so his results this season look legit. Factor in his Gold Glove left field and his postseason experience and you have a player that feels like a match made in heaven to these new-look Yankees.

Other options: Ian Happ, David Peralta, Ramon Laureano, Joc Pederson


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The Relievers:

RHP David Robertson

We stay on the theme of familiarity with a pitcher who has logged nearly five-hundred regular season innings in pinstripes with Robertson. He has had a resurgence in Chicago this season, registering in the 91st percentile in whiff percentage and 61st in barrel percentage. The 11.9% walk rate is well above his career 9.4% mark, but for the most part has looked like the pitcher he was during his time in New York. He is garnering a lot of interest early on and looks like someone who can be packaged with one of the Cubs’ other trade chips.

LHP Joe Mantiply

At age thirty-one Mantiply has finally put it all together as an analytics darling in 2022. He holds a ridiculous 98th percentile barrel rate, 100th percentile walk rate, and a 99th percentile chase rate, essentially checking all the boxes as an elite reliever. Arizona may feel like they found a diamond in the rough worth holding on to long-term, but if they chose to move him expect heavy interest, including from the Yankees.

RHP Daniel Bard

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The beautiful thing about baseball is there is an infinite number of ways to succeed, leading to stories like Daniel Bard. Bard flamed out of the majors in 2013 only to return six years later with Colorado, and the adjustments which got him back are starting to pay dividends. He has completely abandoned his once signature four-seam fastball in favor of a hard sinker. He doesn’t get a ton of bite on the pitch but at 98 mph it is effective. If the Yankees feel like they can extract even more he has a chance to be a high-leverage weapon for them down the stretch.

Other options: Anthony Bass, Gregory Soto, David Bednar, Scott Barlow, Mark Melancon


Wild Card

C Willson Contreras

While reports have pegged the Mets and Astros as favorites for the three-time All-Star backstop, it may be too soon to count the Yankees out. Remember Anthony Rizzo was supposed to be in Boston? Jose Trevino has done an admirable job thus far and the Yankees seem reluctant to add a new catcher to the mix this late in the season, but is that enough to deter them? Contreras is amidst arguably his finest offensive season, sporting a career-high .373 OBP while maintaining a 91st percentile hard-hit rate. If the Yankees fail to land a massive offensive upgrade in the outfield will they be content with a bottom third of Hicks – Kiner-Falefa – Trevino? Expect Cashman to keep a close eye on the dealings of the Cubs, who should hold him in good favor after sending them now top-100 prospect Kevin Alcantara last summer.

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I hope this gave you an idea of the immense number of options the Yankees have this upcoming deadline. While the Yankees may miss on both Soto and Castillo the only measure of success or failure will be determined this fall. As a fan I am optimistic as I believe the pieces are out there to help seal a 28th championship, it’s on the front office to execute.

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