Yankees trade deadline preview: Biggest needs, potential targets, top trade chips before Aug. 2

For most of the season, the New York Yankees flirted with a pace that would challenge the single-season record of 116 wins. Even if they don’t get to 116 wins, and even if they don’t finish with the best record in MLB (the Astros and Dodgers are charging hard), New York is a postseason lock and a good bet to win the AL East for the first time since 2019 .

Last year, the Yankees traded Anthony Rizzo, Joey Gallo and others at the deadline because they needed help just to make the postseason. This year they are a postseason lock to prioritize players who can have a huge impact in October, not so much August and September. However, GM Brian Cashman said the team’s record won’t change their ultimate plans

“No. At the end of the day, you stay tied to the other 29 clubs,” GM Brian Cashman told SI.com earlier this month. “Myself, (assistant GM) Mike Fishman and our baseball operations staff are getting as much information as we can, sharing as much information as we can on our end with the opposing clubs. You get all the information they provide, ask about a lot of different players to find out what’s real and what’s not really available and then see if you’re a match.”

Cashman led the Yankees with 114 wins in 1998 and that team held up at the trade deadline even though the Yankees were able to land Hall of Famer Randy Johnson. It’s a reminder that even though the Yankees are having a special season, Cashman won’t make a move just to make a move. It should be something that makes sense for the current listing at the current price.

According to FanGraphs, the Yankees are worth roughly $7.7 million under the $270 million third tier of competitive balance. Go over $270 million and their 2023 first-round draft pick moves back 10 spots. The Yankees treated the third threshold as a hard cap in 2019 and 2020. If they do that again, they’ll likely have to get creative to make any impact deadlines financially relevant. Still, it’s the Yankees, and they’re having a great season. This is not the time to put an artificial salary cap.

Let’s preview the Bronx Bombers heading into the August 2 trade deadline.


For a team on pace to win over 100 games, the Yankees have a decent number of needs. Unloading and replacing the overmatched Gallo is a must, though the emergence of Matt Carpenter lessens the need for a lefty power bat. The Yankees seem happy with shortstop Isaiah Kiner-Falefa, but even if they wanted to trade him, the trade market lacks impact shortstops. Any improvements to the offense figure to come in the outfield and perhaps on the bench.

The recent injury to Luis Severino’s Latino, as well as Jameson Taillon and Nestor Cortes being hit with the regression home run stick over the last few weeks, should push the Yankees into the market for a starter, not just an innings player. The stars are aligned to trade a hitting pitcher. Any contender could use some bullpen help and the Yankees are no different, especially with Aroldis Chapman and Jonathan Loaisiga not performing as expected and Michael King is now out for the season.

Potential targets

Might as well start with the biggest name on the market, shall we? Soto recently turned down a $440 million extension and the Nationals will consider trade offers. You’d have to give up your first-born and second-born (and more) to get a player this good and this young, but the team that gets the generational talent will win the deal, not the team that has the prospects. (I direct you to the Miguel Cabrera trade.)

Soto would replace Gallo in New York’s lineup, and he’s under team control through 2024, so the Yankees would get him for three games into the postseason. Also, Aaron Judge turned down a big extension to his own spring training. Acquiring Soto would give the Yankees a little extra leverage in Judge’s contract negotiations and even allow them to move on completely. Losing Judge would have stung, no doubt, but having Soto would have softened the blow.

After all, when a player as good and young as Soto comes along, the front office of a big-market team like the Yankees has to go after him. Players like this rarely come around. Soto fits New York’s lineup right now and would give them a centerpiece for what could be a post-Judge world in 2023.

Soto is the best case scenario, and Reynolds is the next best thing as a productive, contact-oriented hitter who gets on base and has power and can play center field. His game is similar to Yankee Bernie Williams of the dynasty era of the late 1990s. Reynolds is also under team control through 2025, so trade for him and it’s both a win now and a win later. Pirates come at a high price, and understandably so. The price to acquire Reynolds may be out of New York’s comfort zone, but as Theo Epstein said when he was bolstering the Cubs at the 2016 trade deadline: if not now, when?


When Benintendi was unable to play in Toronto earlier this month due to his vaccination status, seemed to be closing the door on a trade with the Yankeesbut this is not the case. They stay in the mix (The Yankees have one more regular-season series in Toronto and could see them through the postseason) and Benintendi, on loan, is essentially the polar opposite of Gallo offensively. He is a high contact/low power bat and has AL East and big market experience from his time with the Red Sox. Benintendi will be moved at the deadline. The Yankees are as reasonable a destination as any other team.


Unlike Benintendi, Happ is not a rental. He will remain under team control through 2023, which could appeal to a Yankees team that isn’t sure if they will re-sign Judge after the season (I think they will, but it’s not a lock). The first-time All-Star has cut his strikeouts significantly this year and is now a solid all-around shooter. The Yankees and Cubs were linked about trading Rizzo last year, and perhaps Chicago’s familiarity with the Yankees’ farm system will help facilitate a Happ deal.


Soto is Plan A, Reynolds is Plan B, Happ is Plan C and a guy like Peralta figures to be Plan D. The Diamondbacks are loaded with young outfielders, and the soon-to-be 35-year-old Peralta is gone one way or another at the deadline , or as a free agent after the season. He is an accessible lefty who punishes righties and is a sneaky good left fielder. Peralta may not be the sexiest name, but he represents an upgrade over the current version of Gallo and would extend New York’s lineup without requiring a significant package of prospects.


Every contender wants Castillo, a 29-year-old two-time All-Star with upper-90s gas and one of the best changeups in the game. The Yankees saw it firsthand two weeks ago when Castillo marched into Yankee Stadium and took a no-hitter into the sixth inning and finished with one run allowed in seven innings.

The Reds have been shedding payroll since the end of the season, and the deadline could be an opportunity for the Yankees to use their financial muscle by taking on a bad contract to lower the prospect cost of Castillo. Mike Moustakas is owed roughly $27 million through 2023. If that’s too much, Mike Minor (about $4.5 million left this year) or Tyler Naquin (about $1.4 million left this year) could work in their place. Either way, Castillo is an obvious fit for the Yankees as 1B opposite Gerrit Cole’s 1A, plus he’ll remain under team control next season. It is not for rent.


The question is not if the Athletics will trade Montas, but when will the Athletics trade Montas? A recent bout of shoulder inflammation came at a bad time, though Montas looked fine in his return last week and never went on the injured list. When healthy, Montas is on par with Castillo and is also under team control next season. The two are very comparable. However, Castillo is coming off a recent shoulder problem. But if Montas is truly healthy now, he might be the better option for the money.


How about a third stay in stripes? Robertson, 37, is having a fantastic season, his first full season since Tommy John surgery, and he’s the kind of high-leverage rental reliever that can help any contender. Robertson also passed every “can he handle New York?” test in his previous two stints with the Yankees. He can close, he can set up, he can pitch in middle relief, you name it. Robertson is an ideal modern reliever given his ability to disappear with bats and his versatility.


The Rockies are doing some weird things, but I think even they know they have to trade Bard, a 37-year-old soon-to-be free agent. Bard has an upper-90s sinker and both misses bats and gets ground balls, which is exactly what the Yankees are building their bullpen around these days (think Clay Holmes). Walks can be a concern at times, especially given his history with the yips, but Bard is a bona fide, high-leverage reliever, and the Yankees could use one right now.


An ugly ERA (over 7.00 for most of the season) hides a pitcher with a new sweeper skid and a propensity for poor ground contact with powerful sinking. The trade of Matt Chapman and Matt Olson lowered Oakland’s defense tremendously, and Trivino saw a ton of ground balls slip by as a result. He’s a much better pitcher than his ERA would lead you to believe, and he’s exactly the type of guy that smart teams target with a low buyout (like the Yankees did with Holmes last year).

Exchange chips

Gallo has little to no trade value and is a trade-off candidate at best. Padres GM AJ Preller briefly overlapped with Gallo when he worked in the Rangers front office and has long been a fan, and Preller could jump at the chance to get Gallo on the cheap. However, it will not bring significant returns. Neither is 2018 AL Rookie of the Year runner-up Miguel Andujar, who is buried in Triple-A and has requested a trade (several times). These two aren’t necessarily “commercial chips”, but they are very affordable.

The Yankees have three consensus top-100 prospects in outfielder Jasson Domínguez and shortstops Anthony Volpe and Oswald Peraza. Outfielder Everson Pereira and left-hander Ken Waldichuk also appeared on some top 100 lists. Yankees love… love — Volpe and he will likely be banned, maybe even in the Soto trade. Dominguez is not untouchable, but he will be difficult to release. I think Peraza, Pereira and Waldychuk are the best prospects the Yankees are willing to deal at the deadline.

Last year, the Yankees used the deadline to clear the looming 40-man roster. They have a deep farm system, so instead of potentially losing prospects in the postseason Rule 5 Draft, they can put a few together to get big league help. Catcher Josh Brough, left-hander Matt Crook and right-handers Johnny Brito and Randy Vazquez are on the 40-man roster and could be suspended at the deadline. Brough, Brito and Crook are also Triple-A, near-MLB players, making them attractive to rebuilding teams that don’t want to wait for a prospect to develop in the lower minors.

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