The Pirates sit at the bottom of the NL Central, and have already fired their manager this season. They are a long way from being back in contention. Meanwhile, Paul Skenes has become a must-watch pitcher for their club and helped to invigorate the fanbase, but the Pirates will be irrelevant during his tenure with the club. He is scheduled to reach free agency after the 2029 season, and each pitch he throws for the Pirates takes away some of his value. This is even more true when teams consider that even the most durable pitchers will inevitably have some impact on their careers due to injury. Pittsburgh doesn’t want to trade him away, but it might be the best thing for the club’s long-term growth.

So, why would the Twins want to make this trade? Minnesota already has one of baseball’s best starting rotations, with depth built in the high minors. However, the Twins’ winning window may slowly be closing, with aging stars like Byron Buxton and Carlos Correa in the middle of the lineup. If the Twins want to go all-in, the next two or three seasons are the club’s best opportunity to make an extended playoff run. It would take quite the package of prospects, but the Twins have multiple ways of acquiring Skenes. 

Trade Package 1: Walker Jenkins, Kaelen Culpepper, Connor Prielipp, Billy Amick
It seems likely for Jenkins, Minnesota’s top prospect, to be the starting point for any trade involving Skenes. He is considered one of baseball’s top prospects despite missing time during his first two professional seasons. The Twins hope he can return to the field in June, and that could give the Pirates time to evaluate the young outfielder as a potential cornerstone for their franchise. 

Culpepper is one of the fastest-rising prospects in the Twins organization. As last season’s first-round pick, he’s posted a 160 wRC+ at High-A this season. The Athletic’s Keith Law recently updated his top-50 prospect list, and Culpepper slid in at No. 45. Prospects with rising stocks tend to be dealt with in July, and Culpepper fits this mold. 

On the pitching side, Prielipp has established himself as a top-100 prospect this season with his performance at Double-A. He’s one of the highest-upside arms in the Twins system, and could be a long-term rotational option for Pittsburgh. Like Culpepper, Amick is another player with rising stock, including a 167 wRC+ at High-A. Amick may never develop into a superstar, but he has the potential to be a regular big-leaguer, and that has significant value. 
Overall: Three top-100 prospects, including Jenkins, is the type of deal it will take for Skenes. 

Trade Package 2: Emmanuel Rodriguez, David Festa, Kyle DeBarge, Dasan Hill
The first trade package offers significant long-term upside, while the second package includes both immediate value for the Pirates and long-term building blocks. Rodriguez is on the cusp of the big leagues with a 120 wRC+ at Triple-A, including a bat that has been heating up in recent weeks with a .969 OPS in May. His unique skill set, including a patient approach, powerful swing, and defensive versatility, could make him the headliner for the Pirates. He isn’t as highly rated as Jenkins, but he is still considered one of baseball’s top prospects. 

Festa could immediately be added to the Pirates rotation. He has one more year of team control than Skenes does, and has demonstrated plenty of upside during his time at the major-league level. It’s important to note that Festa dealt with some shoulder soreness earlier in the season, so the Pirates would want to clear his medicals before trading for him. 

DeBarge has been one of the most exciting Twins prospects this season. The 33rd overall pick in last summer’s draft has posted a 133 wRC+ at High-A. He’s also shown the ability to play multiple infield and outfield positions, which can help a player find a role at the big-league level. The Twins selected Hill in the fourth round of the 2024 MLB Draft out of high school in Texas. At Low-A, the 19-year-old has mowed through lineups with a 41.2 K% and held batters to a .121 BA. Hill is a long way from the majors but has some of the most significant upside in the system. 
Overall: Two near big-league-ready assets and two upside plays can make a deal work.

Minnesota’s front office has taken a cautious approach at most trade deadlines, so it seems unlikely for the Twins to mortgage the entire farm system on one starting pitcher. There is also no indication that the Pirates are interested in trading their star player. He has made it clear that he wants to stay in Pittsburgh and help the organization get back into contention. Still, it’s fun to dream of what a blockbuster trade could look like for the Twins and Pirates. 

Which trade are the Pirates more likely to accept? Should the Twins go all-in at this trade deadline? Leave a comment and start the discussion.