Yankees trade deadline preview: Biggest needs, possible fits, top trade chips leading into July 30

At 51-47, the New York Yankees are well out of the AL East race and 3 1/2 games behind the second AL wild card spot, and they’ve developed a knack for “gut punch” losses, as manager Aaron Boone calls them. The Yankees are 3-3 when leading by at least four runs in the eighth inning or later this month. The rest of MLB was 129-4 in such games going into Monday’s action.

“We’ve got the [Red Sox today] and we’ve got to go out and get a win. That’s kind of been our mindset here for several weeks now,” Boone told reporters, including’s Brendan Kuty, when asked about the trade deadline this past weekend. “We understand the situation we’re in. We can’t control what moves are or aren’t going to be made. We’ve got to try and rack up wins.”

Despite the heartbreaking losses, the Yankees are expected to buy prior to Friday’s trade deadline (there is little chance they sell at this point), though to what extent is unclear. New York was inactive the last two deadlines and they have less than $4 million to spend under the $210 million luxury-tax threshold, according to Cot’s Baseball Contracts. Staying under the threshold is a goal.

“I’m going to seriously consider doing whatever I need to do,” chairman Hal Steinbrenner said when asked about possibly exceeding the threshold earlier this month. “… If a piece comes up that I think is a good piece and that baseball ops thinks is a good piece and something we should do, I would absolutely consider doing it.”

In terms of making roster upgrades, the “win at all costs” era has been replaced with the “seriously consider” era in the Bronx. The Yankees are within striking distance of a postseason spot but have several glaring weaknesses and needs. Here’s a look at where they stand heading into the July 30 trade deadline.


First and foremost, the Yankees need an outfielder. Center fielder Aaron Hicks is done for the season and their smorgasbord of left fielders (Miguel Andújar, Clint Frazier, Tim Locastro, etc.) were all ineffective before getting hurt. New York’s center and left fielders are hitting a combined .209/.299/.343 this year. That is untenable. An outfielder is a must, ideally a left-handed hitter.

The Yankees also need pitching, which makes them no different than any other team this time of year. Corey Kluber (shoulder) and Luis Severino (Tommy John surgery) are working their way back from injuries but are still weeks away, so it’s difficult to count on them. Nestor Cortes Jr., Michael King, and Asher Wojciechowski have each taken a spin as the No. 5 starter recently.

The bullpen was expected to be a significant strength has instead been a weakness of late, with trusted late-inning relievers Chad Green, Jonathan Loaisiga, and Aroldis Chapman all contributing to crushing losses the last few weeks. Zack Britton has missed most of the year with injuries and has looked rusty since his return last week. Reinforcing the bullpen would be smart.

Put the shopping list in order and it’s an outfielder (no internal help coming) followed by a starting pitcher (Kluber and Severino are expected back at some point) followed by a reliever (it’s not unreasonable to expect the guys on the roster to perform better going forward). That plus general depth figure to be the priorities for the Yankees going into the deadline.

Potential targets

It is only a matter of the until the Pirates trade lefty Tyler Anderson, a capable starter on a one-year contract having a nice season. He is a bit of a stathead favorite given his ability to induce weak contact and tunnel his pitches together. Anderson is owed less than $1 million the rest of the season and would fit neatly into New York’s luxury-tax plan. He’s not a difference-maker, though he would be an upgrade over their current No. 4 and 5 starter options.

The Yankees believe in exit velocity as an evaluation tool and only a handful of players in baseball hit the ball harder than Rangers slugger Joey Gallo, and the few that do already wear pinstripes (Aaron Judge and Giancarlo Stanton, most notably). Gallo is an excellent defender and would give the Yankees much-needed lefty power. He would also add more strikeouts to a lineup that already strikes out a little too much, so while he’s an obvious upgrade, he’s an imperfect fit. Gallo will remain under team control as an arbitration-eligible player in 2022.

Reports indicate the Yankees already touched base with the Twins about several players, including Byron Buxton and Andrelton Simmons. I assume they also asked about José Berríos. The Yankees have inquired about Max Kepler as well, who would address multiple needs as a lefty-hitting outfielder. Kepler is also signed affordably through 2023 with a club option for 2024, so he’s a long-term addition. There are reasons to believe Kepler can be better than he has been to date (very strong chase rate and exit velocity, among other things.) and the Yankees had success poaching Hicks from Minnesota years ago.

Starling Marte reportedly rejected a lowball extension offer last week, and now the Marlins are likely to trade him. The Yankees were said to have interest in him last trade deadline and that interest could linger even though he’d be another righty bat in a righty-heavy lineup. Marte is having an excellent season and is a legitimate center fielder, and would push Brett Gardner back to his more familiar left field. At this point, a Marte trade is inevitable, and the Yankees are desperate for an outfielder. He fits on the field, though squeezing the $4.4 million still owed to him under the luxury-tax threshold would take some creativity.

The Yankees were connected to Rockies shortstop Trevor Story over the weekend and my hunch is they’re doing their due diligence more than showing serious interest. He wouldn’t come cheap and fitting his $4.8 million remaining luxury-tax number under the threshold would be a headache. That said, Story is an excellent all-around player (though he’s having a down year), and the Yankees could accommodate him by moving Gleyber Torres to second, DJ LeMahieu to first, Luke Voit to DH (once healthy), and Stanton to left field. It’s doable. You need to squint your eyes a bit, but it’s doable. 

If the Yankees blow up their luxury-tax plan, Max Scherzer is the player I think they would do it for. The Nationals ace is a balance of power player. Scherzer can help the Yankees separate themselves in the wild card race, and should they advance beyond the Wild Card Game, he and Gerrit Cole would be a formidable 1-2 punch. Scherzer’s recent triceps issue seems minor but he has full no-trade protection, and who’s to say he’ll want to join the Yankees to chase a wild card spot? Surely other clubs on steadier ground in the postseason race (Dodgers? Mets?) would want him. If you’re the Yankees, you have to at least call Washington to ask.

Potential trade chips

The Yankees currently have three top-100 prospects, according to Baseball America: outfielder Jasson Dominguez (No. 29) and shortstops Anthony Volpe (No. 86) and Oswald Peraza (No. 92). Volpe, a 2019 first-round pick, is having a monster breakout season and Erik Boland of Newsday hears the Yankees have made him off-limits. I would strongly bet against Dominguez being available as well. Peraza is likely the best prospect New York would be willing to part with at the deadline.

Righty Deivi García came into the season as a top-100 prospect but has struggled mightily in Triple-A, making him a less desirable trade target for other clubs. Andújar and Frazier have little value at this point, and it’s unlikely the Yankees will subtract from their MLB roster in a meaningful way at the deadline (Green, Torres, Jordan Montgomery, etc.). Any trades are likely to involve prospects for big leaguers, specifically mid-range prospects for big leaguers.

New York’s second-tier prospects include righty Glenn Otto, the current minor-league strikeout leader, and lefty Ken Waldichuk, who is third in the minors in strikeouts. Otto dominated Double-A and recently moved up to Triple-A. Waldichuk started the season in High-A before moving up to Double-A. The Yankees could push Peraza, Otto, Waldichuk, and hard-throwing righties Luis Gil and Luis Medina on potential trade partners. Outfielder Estevan Florial is another possibility.

Money and the luxury tax will shape the trade deadline for the Yankees. If they’re willing to exceed the $210 million threshold, then they have a world of possibilities. If not, then their pool of available targets will be very small, unless they give up more and/or better prospects to get the other team to eat money. The Yankees have done that before, it should be noted. They got the other team to eat money in the Britton, JA Happ, and Lance Lynn trades at the 2018 deadline.

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