A blockbuster Orioles-Pirates Paul Skenes trade package that stunningly could work

The Pirates have fallen even further back of .500, and there are a lot of crazy ideas floating around regarding what to do with some players. One of the wildest thoughts about where this franchise could go involves entertaining trading Paul Skenes. Jeff Passan is one of the biggest names talking about this outcome and why Pittsburgh should consider it, which is enough to scare any diehard.

Although the season is not over yet, the Pirates completely failed to maximize 2025 as one of the few years they are going to get in their limited time with Skenes. Trading him would be a mistake and could very well put the Pirates into another rebuild. Nonetheless, with the idea out there, and with extension talks sounding more silent by the day, it could be fun to consider the possibilities a trade could bring to the organization.

Dani Wexelman, a radio host for MLB and ESPN, suggested that the Orioles should deliver an overwhelming package to land Skenes. Baltimore has an extremely young core of hitters, while lacking pitching in every facet.

The Pirates are the complete opposite, making this as a perfect trade match. It is extremely unlikely for the Orioles to put together a package that the Pirates would accept. Baltimore would simply have to give up so much to land Skenes, and that may hurt them more than help. That said ... it could be done.

This Pirates and Orioles mock trade for Paul Skenes may work for Pittsburgh.

Headlining this deal would absolutely be Jackson Holliday, the former No. 1 overall prospect in all of baseball. The 21-year-old would immediately give the Pirates a long-term answer at shortstop, with all the tools there to be a superstar. Holliday plays second base now, so maybe when Konnor Griffin is up, this could make for an incredible middle infield.

Another major leaguer in this deal would be Colton Cowser, an outfielder who produced a 4.0 fWAR in 2024. He's got a lot of power upside, despite being on the injured list right now. He would give the Pirates the big bat in the outfield that they need to go with Oneil Cruz and Bryan Reynolds.

Samuel Basallo, the 16th-ranked prospect in all of baseball, would join both big-leaguers in this deal. He is a catcher and first baseman, but regardless of the position, Basallo would give the organization another left-handed bat with excellent hit tools. MLB Pipeline rates his hit tool as a 55 and power as a 60. The 20-year-old has a lot of upside.

Coby Mayo, the 17th-ranked prospect in all of baseball, would also be in this deal. Although he is just 5-for-53 to open up his major league career, his 70-grade power would be a big-time add to the organization. His upside will likely land him at a corner infield position, but with his power, he would find a way into the lineup.

This package is incredibly valuable, and all could immediately jump into the Pirates' starting lineup. Who knows? With how great Skenes is and how much control he has left on his contract, Baltimore may need to add more in this deal. This trade could very well benefit Pittsburgh greatly, yet Skenes is a once in a lifetime kind of pitcher to this organization. That said, the odds of Bob Nutting spending to build around him are slim (as are the odds of Skenes believing in Nutting's future enough to extend), and we saw that in play for 2025. This may be the only way to build a contending lineup in Pittsburgh.

With how lousy the Pirates are right now, there may not be a right or wrong answer to the idea of dealing Skenes. They just lost Jared Jones until 2027 and they don't have a strong farm system with offensive prospects. Skenes will likely stay put in Pittsburgh, but with Ben Cherington on the hot seat, be prepared for anything as he tries to fix his own mess.