Let's be honest — watching Paul Skenes on the Pittsburgh Pirates is sad. That's not because Skenes isn't great, because he's one of the best pitchers in the league. But his 2.15 ERA and 0.92 WHIP look out of place with the Pirates' 21-36, last-place record.
Pittsburgh's principal owner, Bob Nutting, hasn't signed a free agent to a deal longer than one year since 2016, and analysts around MLB have little to no faith that the team will build around Skenes. Jeff Passan appeared on ESPN's "Pat McAfee Show" and said the Pirates should trade Skenes so they don't lose him to free agency for no return.
The Pirates organization has come out and said it will not be trading Skenes, but that shouldn't stop other teams from approaching the desperate club. The Boston Red Sox have more than enough quality prospects in their top-tier farm system to make a deal, and the potential package proposed by MLB insider Bob Nightengale on May 28 could be hard to refuse.
Nightengale said in his latest for The Athletic that the Red Sox should package Roman Anthony, Franklin Arias, Justin Gonzales and Luis Perales in exchange for Skenes. It's an intriguing offer, but the Pirates could probably get a lot more for Skenes. The Red Sox have also been entirely unwilling to listen to trades involving Anthony, so such a deal may be impossible on all fronts.
MLB insider Bob Nightengale proposes Red Sox trade Roman Anthony and more to Pirates for Paul Skenes
Skenes won't be a free agent until after the 2029 season, and that's a lot of service time for another team to buy out. The Nationals got six players in exchange for trading Juan Soto to the Padres in 2022, when he had just two and a half years of service time left. Soto and Skenes aren't super comparable, though, since Soto plays every day and Skenes only pitches every five days. However, Skenes is a generational talent, and he already has a Rookie of the Year award and an All-Star nomination under his belt at just 23 years old.
Anthony is a high price for the Red Sox to pay for any player, but Gonzales, Arias and Perales take Nightengale's trade proposal to another level. Arias, 19, is Boston's No. 4 prospect, and he's slashing .351/.396/.511 with High-A Greenville. Gonzales is just 18, but he's already turned heads and earned a promotion from Single-A to High-A. He's batting .254/.397/.286 after 17 games in Greenville.
Perales is one of the Red Sox's most highly touted pitching prospects, of which they don't have many. SoxProspects.com tabs him as a potential mid-rotation starter in the big leagues, and he'd be an excellent get for the Pirates if they were to trade Skenes. Perales tore his UCL and underwent Tommy John surgery in June 2024 and hasn't pitched since, but he posted a 2.94 ERA with 56 strikeouts over 33.2 innings between High-A and Double-A last year.
The Pirates have made it crystal clear they're not trading Skenes this year, but that doesn't mean a potential trade won't open up down the road — it's almost impossible to think Pittsburgh will convince him to sign an extension, so it may look to trade him in a few years when his value is lower beause he'll be closer to free agency. The Red Sox could have a farm system stocked with prospects for a potential trade with the Pirates down the line, but for now, a deal involving Anthony is about as likely as Skenes re-signing with Pittsburgh as a free agent.