The Yankees Should Trade for Jeremy Pena

By EJ Fagan

June 15, 2026

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The following post comes from EJ Fagan's Substack, Baseball Is Life. It is shared with permission.

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Trade season is just a few weeks away. The Yankees are in a tough spot. They have a pretty full roster, albeit with some long term injuries. While they can no doubt trade for some bullpen arms, they have a logjam at 1b/OF/DH and starting pitcher. That leaves basically three positions to significantly improve: catcher, third base and shortstop.

Unfortunately, it’s pretty darn hard to find significant improvements at these positions. Third base has a reputation as a power spot, but the average MLB third basemen is hitting just .234/.311/.381 in 2026, well below league average. Ryan McMahon has been better than that since roughly mid April, especially on defense.

Shortstop is another story. To date. Yankee shortstops have hit .239/.316/.365 with only above average defense. Anthony Volpe is not hitting to even his 2024 standard. Jose Cabarello has slowed down after having some good batted ball luck (and strong small sample defensive numbers) in the early season. Lots of room to improve.

The obvious target is Jeremy Pena. The Astros star shortstop will be a free agent after the 2027 season. He hasn’t signed an extension and seems unlikely to do so before hitting the open market. The Astros are 31-39 on the season. They don’t like to pay top dollar for free agents. It seem likely that they will trade him.

Jeremy Pena started off the season slow, went down with an injury, and returned in May. Since then, he has hit an impressive .295/.371/.449. His defense hasn’t been up to his usual Gold Glove standard, but I don’t see any reason to believe that he can’t play a good shortstop going forward.

He’s right-handed with moderate platoon splits. He’s got a strong contact swing. He’s a World Series MVP. The dude makes so much sense on the Yankees roster. He would slot in comfortably near the top of the lineup.

But he also makes a lot of sense on other rosters, including the Astros. He won’t come cheap.

Let’s find some comparable trades.

• For one year of Francisco Lindor (and a salary dump Carlos Carassco), the Mets gave up Isaiah Green, Josh Wolf, Andres Gimenez and Amed Rosario.

  
  

• For two years of Matt Olson, the Braves gave up Shea Langeliers, Joey Estes and Cristen Pache

  
  

• For two years of Matt Chapman, the Blue Jays gave up Gunnar Hogland, Zach Logue, Kevin Smith and Kirby Snead.

  
  

• For two and half years of Randy Arozarena, the Rays got Brody Hopkins and Aidan Smith.

I’d describe all of these returns as significant but not stupid. Jeremy Pena is going to require at least one significant piece, either a top prospect like Brody Hopkins or Shea Langeliers or a promising young MLB piece like Andres Gimenez.

So what would it take to trade for Pena? Here’s how I think about it:

• Anthony Volpe

• One of Jasson Dominguez, Will Warren or George Lombard Jr.

• A second mid level prospect like Elmer Rodriguez, Carlos LaGrange or maayyb beee Ben Hess

• A throw in or two

  
  

I think that deal would hurt, but would also be worth it. I’m not sure who the Astros value more between Dominguez, Warren and Lombard Jr, but Dominguez sure feels like an Astros type player. Volpe is the Amed Rosario comp. The mid-level guy makes it worth it for the Astros.

How much competition would the Yankees have if Pena is on the market? A few contenders could use a shortstop. The Braves and Dodgers would probably love a real shortstop, especially given how hard Mookie Betts has fallen off this season. Maybe the Rays and Brewers would like an upgrade too, but neither are often in the business of buying 28 year-olds at the deadline. This doesn’t feel like a bidding war situation to me.

Go get Jeremy Pena, Cashman!