The New York Yankees are looking ahead at what could be one of the most significant trade deadlines in franchise history, but this market is stranger than others. With the third Wild Card in place, teams who are below .500 have a legitimate shot to turn their season around and compete when they would usually be fielding offers for top players on their roster. Whether that’s healthy for the game or not is another conversation for another day, but the Yankees cannot let an obscure market prevent them from adding key pieces.
With a roster that has holes that desperately need to be filled, here’s a three-trade plan I have outlined for the Yankees to fix their issues and become the class of a weak American League.
Adding The Perfect Third Baseman For This Lineup
Matt Chapman 2.4 WAR | 112 wRC+ | .735 OPS | +7 DRS | 0 OAA | FA: 2026*
The San Francisco Giants could do a bit of buying and selling, and with the season Matt Chapman is having he could find himself back on the free agent market this winter thanks to his opt-out. It’s a risky gamble to take knowing that he can opt into another year of his deal at roughly $18 million towards the Luxury Tax, but it’s one worth making given how desperately this team needs a third baseman. After slumping hard in the second half of 2023, Chapman has bounced back nicely with a 112 wRC+ and 14 home runs through 100 games, providing value on all sides of the ball.
He’s a positive contributor with the bat while having +2.4 Baserunning Runs and +2.8 Defensive Runs on FanGraphs, and that’s exactly what this team could use. An excellent athlete with good power and a watchful eye, Matt Chapman could settle atop the Yankees’ lineup, providing a bat who (in theory) should have an easier time getting the ball out of the ballpark in a place like Yankee Stadium where the corners are more pulled in than in San Francisco. While he’s not a sexy name, Chapman has very quietly posted the seventh-most fWAR for a third baseman (2.4).
Thus far the Yankees have gotten a 76 wRC+ and 0.7 fWAR out of the position, so I’ll gladly take what Matt Chapman provides over the disastrous DJ LeMahieu. As for a potential trade package, I don’t believe the San Francisco Giants would demand a king’s ransom, but this is still a duo of players with some value who could reasonably contribute at the Major League level soon.
- SFG Receives:
- 2B Jorbit Vivas
- LHP Brock Selvidge
- NYY Receives:
- 3B Matt Chapman
Both Vivas and Selvidge are considered top-15 prospects in the organization, with Vivas specifically being on the Yankees’ 40-man roster. Given the Giants’ need for offense and young controllable position players, he could provide exactly what they’re looking for. Brock Selvidge hasn’t had the season many hoped he could, but the stuff is still interesting, and while he deals with bicep tightness on the IL, could still pose a good bit of value to a team looking to stock up on upper-level MiLB talent.
Why It Could Happen: If the San Francisco Giants are confident that Matt Chapman would opt out (and I’d be confident in saying he will), then why wouldn’t they entertain offers for him? I know that Farhan Zaidi hasn’t historically sold at the deadline and that his job could be at stake, but perhaps this recent stretch of mediocrity helps him face the cold truth about success in this league. The Giants are 4.5 games back from a playoff spot and while Alex Cobb and Robbie Ray are legitimate reinforcements, this clearly isn’t the team that you go all-in for.
Making a Stunning Trade to Shore Up the Infield and Lineup
Carlos Santana: 2.1 WAR | 119 wRC+ | .769 OPS | +5 DRS | +9 OAA | FA: 2024
There’s no way the Minnesota Twins would entertain offers on Carlos Santana…right? Full transparency, I’m not at all an insider, this is purely speculatory based on the reports we’ve gotten, but Jeff Passan of ESPN mentioned Minnesota as a team that could both sell and buy. Given the fact that they could be dealing with financial restraints ahead of the trade deadline and their incredible infield depth, they could trade from that infield to save some cash and improve their pitching staff.
Carlos Santana has been remarkable in his age-38 season, posting a 119 wRC+ with 14 home runs and 20 doubles as he’s stabilized the middle of the Twins’ order. The switch-hitting first baseman is an excellent all-around hitter, providing some power, patience, and contact all in one profile. He’s the kind of hitter who would love hitting at Yankee Stadium as well, and he would fit perfectly in the middle of the Yankees’ lineup. Hitting him in between Aaron Judge and Giancarlo Stanton would be excellent for balance and depth purposes, and the team would have a new-look offense.
The concerns of slow bat speed or struggles with velocity that usually persist aren’t there with Santana, who has a wOBA north of .360 against pitches at or above 95 MPH. Defensively he’s still amazing as well, leading American League first basemen in DRS and OAA. With the Twins getting Jose Miranda and Royce Lewis back soon, impending free agent Carlos Santana makes sense as a trade piece to save cash, open up playing time, and get some MLB value back, but who makes sense to acquire from the Yankees?
- MIN Receives:
- Nestor Cortes
- NYY Receives:
- Carlos Santana
Early deadline reports have suggested that the Twins have shown some interest in Yusei Kikuchi and Nathan Eovaldi, but the Texas Rangers are starting to lean more toward buying with the Mariners and Astros failing to run away with the AL West. As for Kikuchi, the Twins could get an extra year of control at a lower AAV if they pivoted towards Cortes instead, who also has the better ERA between the two starters. Nestor Cortes has been a league-average starter this season, but two years of an okay starter could be valuable enough to land you half a season of a good first baseman.
I love Ben Rice and think he’ll become a good player, but if the Yankees land someone with the fifth-best fWAR (2.1) among first basemen, they’re getting better. It’s about winning in 2024 at the moment, and Rice is a great emergency option if one of Giancarlo Stanton or Carlos Santana were to go down entering October.
Why It Could Happen: The Twins are not going to add much payroll if any at all this deadline which means they’re going to have to get creative. Jeff Passan isn’t the only person to report about this financial crunch either, and the Twins have three infielders on the way back from the IL who have a higher OPS+ than Carlos Santana this season. I’m not saying this is a lock to happen, we don’t even know if the Yankees are shopping for a first baseman right now, but this could be a mutually beneficial trade that helps both teams.
Bolstering the Rotation With a Big-Time Starting Pitcher
Jack Flaherty: 2.5 WAR | 2.95 ERA | 3.09 FIP | 27.5% K-BB% | 104 Pitching+ | FA: 2024
If the New York Yankees decide to go after any starter, it should be Jack Flaherty, and that’s thanks to his excellent trio of pitches that include a four-seamer, slider, and curveball that can carve through any lineup. With a 2.95 ERA through 18 starts, the right-hander has proven to everybody that he’s the kind of pitcher that you want taking the ball near the top of your rotation thanks to his high strikeout rate and low walk rate. When a pitcher can miss bats as often as Flaherty can with the nasty breaking stuff that he has, he’s a nightmare for any hitter when he’s on the mound.
The Detroit Tigers are most definitely trading him away, and while there will be plenty of suitors, the Yankees need to make sure they’re heavily involved in these sweepstakes. Gerrit Cole has not gotten off to a sparkling start while Marcus Stroman and Carlos Rodon have slumped, and while Clarke Schmidt’s return could help, they’ll need some external additions as well to go alongside him. Luis Gil’s new slider is awesome and I have a ton of faith in him staying on track, but Flaherty could give the Yankees a fearsome rotation for the postseason.
- DET Receives:
- RHP Will Warren
- SS Roderick Arias
- SS Ben Cowles
- NYY Receives:
- Jack Flaherty
It seems like a lot to give up Roderick Arias, but he’s clearly a work-in-progress and his stock in the organization has taken a massive hit due to really low in-zone contact rates. Still, he’s a fast and athletic shortstop with the power and projectability to potentially become a stud, and I think that’s a flier that the Tigers would consider worth taking. I know Will Warren hasn’t had a great Triple-A campaign, but I think his ERA is a facade and that the stuff still plays at a very high level.
His four starts in May have completely tanked his season numbers, as he’s been impressive outside of that stretch, and I think the Tigers could view him as a near MLB-ready option. Benjamin Cowles has mashed this season seemingly out of nowhere, posting a 139 wRC+ in Double-A with the Somerset Patriots while running a mere 18.1% strikeout rate and generating a ton of contact in the air. With his excellent play at the plate, he’s also been a strong defensive infielder, with a chance to really stick at shortstop.
It’s two top-10 prospects and a top-30 for half a season of Jack Flaherty, and while I could see another team bidding more (and I’d completely understand why), I don’t think this package is too far off of what the Tigers could be looking for.
Why It Could Happen: This is going to be my briefest explanation of the group; the Tigers are 100% trading Jack Flaherty and the Yankees could use a guy like him to take the ball in Game 2 of a postseason series. Plain and simple.
The Finishing Touches For the Yankees’ Bullpen
A.J. Puk: 0.6 WAR | 4.30 ERA | 3.62 FIP | 11.5% K-BB% | 102 Pitching+ | FA: 2027
A.J. Puk has been excellent out of the bullpen for the Miami Marlins after struggling to make the transition to being a starting pitcher. He posted an ERA north of 9.00 through his first four starts of the season, but after being moved back to the bullpen the ERA has dropped to a sparkling 2.08 with a 28.9% strikeout rate. Puk is trending in the right direction as well, with the southpaw adding a sharper slider that prioritizes vertical drop and velocity over the horizontal action his sweeper was known for.
This shift from a slider to a sweeper has seen him go on a tear that includes 14 straight outings without allowing a run where he has struck out 43.9% of batters faced. The stuff is electric, and with multiple years of control after the 2024 season, he could transition into the closer role for New York if they’re unable to retain Clay Holmes this winter. His fastball sits in the mid-90s, his primary breaking ball is disgusting, and he misses a ton of bats, there’s not really a reason the Yankees shouldn’t be interested (outside of the fact that he would look gross without a beard in my opinion.
Anthony Bender: 0.5 WAR | 3.99 ERA | 2.99 FIP | 16.9% K-BB% | 108 Pitching+ | FA: 2028
A fun project reliever for Matt Blake and Sam Briend to try and fix up, Anthony Bender has a wicked sinker-slider combination that’s resulted in a 2.98 FIP and 3.57 xERA (which are great) but a mere 3.99 ERA. (not great). He has a 117 Stuff+ and command isn’t a problem for him, so why hasn’t it all magically come together for him as it did through his first two seasons in the league where he had a 2.90 ERA and 27.1% strikeout rate?
Well, he’s tweaked the slider to become more of a sweeper, which is great because it’s the best version of the slider he’s thrown at the Major League level results-wise, but I think it creates a massive hole in his game. Having a gyro slider with good vertical drop keeps left-handed batters honest, having just a big loopy sweeper only creates an easier matchup for left-handed batters, who have a mere 18.3% K% and .367 OBP against him. Throwing a gyro slider again alongside the sweeper could really help him, and his sinker wouldn’t have to be a pitch he relies upon so heavily against lefties.
It’s a bit of a crapshoot to see if he can find it or not, but Bender has three more years of club control after the 2024 campaign and would be an upgrade over internal options. If he doesn’t work out, he does still have three MiLB options, so that should be noted as well. It’s a low-risk project who could take off or find himself on the Scranton shuttle.
- MIA Receives
- SS Jared Serna
- RHP Cam Schlittler
- 2B Anthony Seigler
- C Rafael Flores
- NYY Receives:
- LHP A.J. Puk
- RHP Anthony Bender
The Yankees are parting ways with infield prospect Jared Serna who has been a solid bat in High-A with good projectable skills across the board, and his teammate Cam Schlittler goes alongside him. The right-handed starter has posted a strong ERA with good strikeout numbers thanks to a good breaking ball and a pretty strange fastball that has cutting action at high velocities. Anthony Seigler was a former first-round pick who has started to hammer the baseball thanks to a shift in approach, pulling the ball in the air more often and seeing his MiLB career turn on a dime.
Rafael Flores is a catching prospect who just got to Double-A, and his power is finally being tapped into as he’s lifted the ball in the air more. The UDFA has some contact issues but I think the defensive skills are strong behind the dish, and the Miami Marlins have to improve their catching depth internally. It’s more of a quantity-over-quality package, but I think all three of these prospects would enter into the Marlins’ top 30 immediately.
Why It Could Happen: The Yankees need relievers and the Marlins are awful, and both of these names bring some more swing-and-miss (especially Puk) with years of control after the 2024 and 2025 seasons. They need insurance in their bullpen for the next couple of seasons, and I think both of them can contribute at a very high level. Tanner Scott is right there, but I think A.J. Puk will end up being the better get from a value standpoint at a potentially lower price. Only time will tell.
Final Roster and Thoughts About the Deadline Plan
It’s easy to say that the Yankees’ problems can’t be fixed at the deadline, but I’m sure every team besides the Phillies is hearing that from their fanbase right now. The Yankees have flaws, and not all of them will be addressed, but the duo of Aaron Judge and Juan Soto create a massive margin for error. Offensively, this group should be more than good enough with the proposed additions I laid out, and I’d argue they could match up with any in the sport thanks to their aforementioned dynamic duo:
Six hitters with a wRC+ above 110, two hitters who are right below the league average, and one hitter who can quickly be replaced by Jasson Dominguez when he’s ready. Not bad at all, and you could walk away with an even better lineup if you were to acquire someone like Isaac Paredes instead of Matt Chapman or Gleyber Torres keeps the momentum going after a hot stretch as of late.
On the pitching side of things, I feel equally confident that this group can get the job done. Gerrit Cole, Luis Gil, Jack Flaherty, and Clarke Schmidt are an awesome 1-4, and the bullpen is shut down with their trio of A.J. Puk, Clay Holmes, and Luke Weaver coming into late-game situations. Anthony Bender should be able to support a middle bullpen that includes Tommy Kahnle, Michael Tonkin, and potentially other arms like Ian Hamilton or Scott Effross who could make their returns this summer.
It’s a revamped roster that should be able to put up runs and sit down opposing batters, but we’ll see how Brian Cashman navigates through this year’s trade deadline in less than a week.