Houston Astros shortstop Jeremy Peña recently changed representation, hiring Scott Boras as his new agent as he nears the completion of his fourth year of big-league service time. That schedule means he’s set to hit free agency after the 2028 season. His new agent, however, isn’t stopping the Astros from pursuing an extension. Astros general manager Dana Brown divulged Sunday that he let Boras know that he’s “still interested in signing Jeremy long-term” and that he’ll “be in touch” regarding a possible extension. (Brown also went public about his intention to extend a different Boras client, Alex Bregman, without a deal ever coming to fruition.)
Peña, 27, has developed into Houston’s most productive player. This season, he’s hitting .322/.378/.489 with 11 home runs and 15 stolen bases. His 143 OPS+ would represent a new career high and his half-season 4.5 estimated Wins Above Replacement puts him on pace to obliterate his current best (5, back in 2022). For his career, he’s averaged more than 5 WAR per 162 games — that despite not yet making an All-Star Game or winning an individual regular season award other than a Gold Glove in 2022.
If you compare Peña to all shortstops, he ranks fifth in WAR since the start of the 2022 season — that’s ahead of the likes of Dansby Swanson and Willy Adames, among others. It’s easy enough to understand why the Astros would want to extend Peña’s contract, especially since he’ll have just two seasons of team control remaining after this year. But how much might such an endeavor cost?
The secret to predicting the future in baseball is to look at the past — and, specifically, to look for situations that most closely resemble the one at hand. To wit, while it may be tempting to refer to the recent free-agent contracts signed by Swanson ($25 million annually) and Adames ($26 million annually), the way these things work is that a player’s contract will be discounted from their true value until they reach free agency. (The exact discount rate varies based on their distance from that date.) If Peña were a free agent this winter, he would undoubtedly clear those average annual values. He’s not, though, so any extension he signed would likely reflect his remaining team control.
With that in mind, here’s a complete list of shortstops with at least two years of service time to sign extensions of four years or longer since 2021, according to MLB Trade Rumors’ contract database:
Finding an exact comparison point isn’t easy. Giménez and Fletcher are included because they had played some shortstop leading up to their extensions; Giménez still has the defensive chops to swing it, but I think it’s fair to ignore Fletcher as a point of comparison. The same might be true for Witt and Tatis, both of whom were a few years younger at the time of their extensions. Meanwhile, I don’t think it would be fair to say that either Perdomo or Crawford were quite on Peña’s level.
Although I can’t point to one of the above extensions as an easy blueprint for the Astros, I do think the spectrum of contracts can serve as guideposts. If Witt and Tatis’ extensions feel a touch rich (they’re nearly at the level that Adames and Swanson received through free agency), and Perdomo, Crawford, and Giménez’s feel way too light … well, you get where I’m going with this. I think you’d be within reason to estimate a Peña extension’s AAV as being within that $22 to $24 million range.
Alas, it’s not that simple. Peña’s age (he’ll turn 28 in September) means he has two obvious extension routes forward: sign a short deal that enables him to reach free agency in his early 30s while providing more certainty upfront, or go for a long-term deal that could encapsulate the rest of his career. If you accept that those are the obvious choices, then you can understand if Boras might resist recommending any extension of team control at all. Yes, there’s the risk of injury or an unexpected decline, but the upside (a payday closer to $30 million annually) might be worth rolling the dice.
In other words: good luck to Brown, because he’s probably going to have his work cut out for him if he stays true to his word on pursuing a Peña extension.
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