Yankees trade scenarios: Bowden weighs 6 proposals to upgrade, address weak spots on roster

By Chris Kirschner, Brendan Kuty and Jim Bowden 

It’s about a month until the MLB trade deadline hits July 30.

Still, it’s never too soon to start looking ahead for the New York Yankees, who have been one of baseball’s best teams but also have weak spots on their roster.

After proposing six hypothetical Yankees trades, we asked former general manager Jim Bowden to weigh in on them.

Alex Bregman appears headed to free agency in the offseason. If the Astros stumble in the coming weeks, would they deal him at the deadline? (Troy Taormina / USA Today)

This may be an overpay for a rental, but the Yankees have what the Astros need: starting pitching. But is it even possible for the two rivals to link up for a player associated with the 2017 Astros? The Yankees could use a different third baseman with DJ LeMahieu looking close to the finish line of his career. Bregman has also been one of the best postseason players over his career and could provide the Yankees with another quality bat in the middle of the order. The Astros have climbed back to .500 and have said they won’t sell, but with how battered their starting pitching has been this season, they could use a reset. — Kirschner

Bowden: I love the concept of the Yankees improving at third base and Bregman, despite a slow start, has come on strong in June, slashing .341/.404/.494. On the season, he has nine home runs and 35 RBIs. Bregman works the count as good as any hitter in baseball and has tremendous plate discipline. He’d also be a great fit in the Yankees clubhouse with his competitiveness and leadership qualities. However, in my conversations with Astros GM Dana Brown, he’s been clear that under no circumstances will they be sellers at the deadline. Since May 1, the Astros have gone 30-20, and they feel confident they will get back to the playoffs for the eighth consecutive season. All that said, for an impending free agent like Bregman, the suggested return seems reasonable if they were to trade him.

The Yankees are in a bind with Gleyber Torres. It’s gotten so bad that manager Aaron Boone has had to sit him the last two games, crossing his fingers for a “reset” from the 27-year-old. And I get it: Chisholm hasn’t played second base since 2022. But he was an All-Star that season as a second baseman and he graded favorably defensively there. He’s 26 years old, under team control until after the 2026 season, and he fills a long-term need for the Yankees, who also won’t hate his ability to play center field. This deal has the Yankees giving up a lot to get him. But for the Marlins, they get a season and a half of Miami guy and mid-rotation arm Cortes, a close-to-ready MLB starting pitching prospect in Selvidge and a talented youngster in the dynamic Arias (ranked the No. 98 prospect in baseball by The Athletic’s Keith Law before the season). — Kuty

Bowden: I love the idea of the Yankees going after Chisholm, who is sure to be traded between now and July 30, and second base is probably his best position. He provides a rare combination of speed and power and I think being around veterans like Aaron Judge, Juan Soto and LeMahieu would help him develop into a much better player. However, Miami has no interest in a pitcher like Cortes as the headliner because they’re looking for either prospects or non-arbitration-eligible players. For Chisholm, they’d be seeking a package centered around right-hander Will Warren and a power bat like Everson Pereira with center fielder Jace Avina as the final piece.

Rockies get: RHP Will Warren, OF Brando Mayea

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Ryan McMahon is signed through 2027. He is making $12 million this year and will make $12 million in ’25, $16 million in ’26 and $16 million in ’27. (Jesse Johnson / USA Today)

If Colorado makes McMahon available, the competition for him will surely be fierce. But he’s also in the middle of a career year at the plate (124 OPS+). The Yankees aren’t going to want to overpay too much. But the 29-year-old McMahon would likely give them their everyday third baseman through the 2027 season. In Warren, the Yankees would be surrendering their top healthy pitching prospect who struggled initially at Triple A before turning it back around in his last five starts (3.12 ERA). Mayea is just 18 years old, but the Yankees gave him a $4.35 million signing bonus in 2023. He’s powerful, fast and should remain in center field for the long haul. Law ranked him as the Yankees’ No. 12 overall prospect before this season, but said he has “probably the best chance of any of their non-top 100 prospects of exploding onto the list next year.” — Kuty

Bowden: I think this trade makes a lot of sense for both sides. McMahon would be a perfect fit to become the Yankees next third baseman. The suggested return is fair market value in my opinion, although if I’m the Rockies, I’d try to get Oswaldo Cabrera included as a fourth player in the deal.

Marlins get: SS Oswald Peraza, UTIL Oswaldo Cabrera

It may be a slight overpay from the Yankees, but Scott should have numerous suitors. The Yankees need bullpen help. They’ve cycled in relievers Tim Hill, Phil Bickford and Yoendrys Gómez over the past couple of weeks with the hope that at least one of them sticks around. They should get Scott Effross back soon, and JT Brubaker may transition to a bullpen role, too. But getting Scott would give the Yankees a formidable back-end option to pair with Clay Holmes. In this scenario, the Yankees part with Peraza, a former top prospect who doesn’t have a clear path to the major-league club and Cabrera, a utility option who has shown promise but hasn’t broken through in a bench role. — Kirschner

Bowden: The Marlins should jump at this offer because I don’t think they’re going to do any better elsewhere. Peraza would become the Marlins’ starting shortstop and Cabrera their super-utility player. Both of them are blocked by better players on the Yankees, which makes them expendable. Peraza still has significant upside despite not showing it in the Bronx.

Tigers get: OF Everson Pereira, SS Oswald Peraza, RHP Clayton Beeter

The Yankees could use another starting pitcher. It’s not their biggest need but adding Flaherty would give them another option if Luis Gil ends up seeing his workload reduced, or if Carlos Rodón’s poor underlying metrics continue to catch up with him and he becomes a less-trusted option. Flaherty has been one of MLB’s best strikeout artists this season and he’s massively improved his command compared to last year with St. Louis and Baltimore. The Tigers could use more power. Pereira is out for the season after undergoing elbow surgery. He should make a full recovery. When healthy, he has 20-plus home run potential if he can control the zone better. Beeter profiles as a reliever long term but the 25-year-old has started in the minors with the Yankees. — Kirschner

Bowden: Based on what I’m hearing from opposing GMs, the Yankees are not looking to add another starting pitcher as they are happy with their group that includes Gerrit Cole, Gil, Rodón, Marcus Stroman, Cortes, and Clarke Schmidt. The industry believes if the Yankees trade from their farm system it will be to improve at second base, third base or in the bullpen. 

Angels get: OF Everson Pereira, RHP Ian Hamilton

Rengifo is not the best available infielder the Yankees could acquire, but if they don’t shoot for the top of the market, he wouldn’t be a bad option. His underlying metrics aren’t the best, but this is his third straight season of posting an above-average wRC+. He also steals bases — 20 so far this season — and the Yankees could benefit from his speed. The knock on Rengifo is he’s a very poor defender. Perhaps moving him to second base would help but it’s an issue. Estévez has been lights out recently for the Angels as their closer. He strikes guys out and minimizes base runners and would be a perfect fit for the Yankees. Ian Hamilton and Pereira would go to the Angels in this proposal. Hamilton has looked shaky this season and is currently on the injured list but does come with team control through 2028. — Kirschner

Bowden: I also love this trade concept for the Yankees as Rengifo is an underrated player who comes with an additional year of control and Estévez would give New York closing security behind Holmes. However, this deal makes little sense for the Angels. Pereira has huge power but his hit tool is no sure thing and Hamilton will be 30 years old next year. A rebuilding team like the Angels need prospects more than a veteran reliever with a 1.584 WHIP and 4.2 walks per nine innings. Love it for the Yankees, hate it for the Angels.



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(Top photo of Jazz Chisholm Jr.: Gregory Bull / Associated Press)

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