The Pressly Paradox: Why Selling Relievers Is a Precarious Path

Trade deadline season is fully upon us, and the Minnesota Twins are considered by many (including opposing scouts who are flocking to Target Field) to be "open for business." Naturally, the team's assortment of controllable high-octane relief arms are known to be drawing a large share of the interest.  

There is an undeniable logic behind selling high on relief pitchers at the deadline. Contending buyers feel a sense of urgency to shore up their rosters for the stretch, and bullpen help is always in high demand. This leads front offices to pay a premium for widely sought targets. Add in the volatility of relief pitchers in general, and you see why big offers can prove hard to resist.

Jhoan Durán and Griffin Jax are undoubtedly drawing a steady steam of calls with the trade deadline now just days away. Probably Brock Stewart and Louie Varland as well. All are high performers with excellent raw stuff, all are free of injury flags at the moment, and all are controllable for multiple years beyond 2025. The Twins are in position to cash in right now in a big way, if they so choose. 

Plenty of teams have benefited immensely in the past from taking advantage of moments like this. The most famous recent example would have to be Kansas City sending Aroldis Chapman to Texas in 2023, one month ahead of the deadline, receiving back a left-handed pitcher named Cole Ragans. The move worked out in the short-term for the Rangers, who won the World Series, but Ragans became Kansas City's ace almost immediately, helping propel them to the playoffs in 2024 for the first time in nine seasons. Seven years earlier, Chapman was also involved in a memorable win/win deadline swap, going from New York to the Cubs (where he also won a World Series) in exchange for Gleyber Torres. 

The latter example is probably more pertinent to Minnesota's current situation, because back in 2016 Chapman was 28 and at the height of his powers. Even then, he was only a rental — the Yankees would re-sign him the following offseason — but New York still managed to score a prospect on his way to consensus top-10 global status. It took less than two years for Torres to become an All-Star regular in New York.

Those are the kinds of precedents that illustrate why Minnesota's front office would be foolish not to keep an open mind about trading someone like Durán or Jax. The idea of acquiring a game-changing talent who could enter the mix within a relatively short timeframe is enticing, and Minnesota's probably got enough bullpen depth to survive without one of them, especially with Varland's emergence.

But there's a downside and a cost to these types of moves also. Twins fans have seen that, up close and personally.

I've written before about the Ryan Pressly trade, which I consider to be the most regrettable move this front office ever made. In 2018, Pressly was not quite fully established as an elite reliever but well on his way, with spectacular swing-and-miss numbers and swing rates. Still under control beyond the 2018 season, Pressly was an alluring target in the same vein as Durán or Jax — especially to an analytically driven team like Houston.

The Astros made an offer that Derek Falvey and the Twins decided they could not refuse: hard-throwing right-hander Jorge Alcalá and athletic outfielder Gilberto Celestino. Neither of those prospects amounted to much in a Minnesota uniform. 

Meanwhile, Pressly blossomed into an instant bullpen ace for the Astros. He posted a 0.77 ERA the rest of the way in 2018. More painfully, in 2019, which would have been his last year under control with the Twins, Pressly was an All-Star who dominated the late innings as Houston won 107 games and the pushed the World Series to seven games. That year's Twins team, of course, was the Bomba Squad, which one 101 games and the division but fell short in the postseason, in part, because their relievers posted a 9.00 ERA against the Yankees. 

Man, could that 2019 team have used Ryan Pressly. I don't want to overstate things but it very well might have been the difference between getting swept out of the first round and making a deep run in the playoffs. That's a missed opportunity that will always gnaw away at me. Especially because the very next year, Minnesota's bullpen once again flopped in the playoffs, this time against Pressly's Astros as they cruised to yet another ALCS. While the Twins watched their season slip away with a 37-year-old Sergio Romo on the mound in crunch time, Pressly posted a 2.46 ERA and tallied four saves for the Astros as they marched through October yet again.

I share these cautionary tales to underscore why trading any of their top relievers is a precarious path for the Twins, and far from a no-brainer even if the offers feel overwhelming. Dominant late-inning relievers are in short supply, and can make a difference when the stakes are highest like few other players. We've already seen that in the cases of Durán and Jax, whose contributions in tight games were instrumental when the Twins finally broke through and won a playoff series in 2023.

I'm personally not quite ready to give up on this 2025 season, as sour as the outlook may be right now. I fully understand why anyone would be, including the front office as they evaluate their options and their future. But 2026 is very much still in play, with all the requisite pieces in place to put an aspirational World Series contender on the field, led by Pablo López, Joe Ryan, Byron Buxton, Royce Lewis and a hopefully rebounding Carlos Correa. Having a stable of high-end relievers to support this group will be vital to maximizing the opportunity. Subtract from it at your own risk.