MLB Rumors: 3 Blockbuster Trade Proposals To Acquire Pirates' Paul Skenes
ESPN’s Jeff Passan recently argued on The Pat McAfee Show that the Pirates may eventually have no choice but to move their prized pitcher while his value is sky-high, calling him “a candidate for a $400 million pact.”
Though one Pirates source firmly told The New York Post’s Jon Heyman there’s “no chance, no way, no how” Skenes is being moved right now, history suggests otherwise.
Pirates source: Paul Skenes is not getting traded. “No chance, no way, no how,” is the way I heard it. While there’s a bit of logic to such a scenario, superstars just aren’t traded by anyone with 1 year service time and the Pirates remain determined to build around Skenes.
— Jon Heyman (@JonHeyman) May 21, 2025
With the Pirates at 16-33 and ownership known for tight spending, Bleacher Report’s Zachary D. Rymer explored what it might take to pry Skenes away. Here are three blockbuster packages from that list that could test Pittsburgh’s resolve.
1. Phillies Offer Top Pitching Prospect Andrew Painter
To Phillies: RHP Paul Skenes
To Pirates: RHP Andrew Painter, SS Aidan Miller, RHP Mick Abel
This deal would give the Pirates an elite return, headlined by Andrew Painter, widely considered one of the top pitching prospects in baseball. Aidan Miller, a potential impact bat at shortstop, and former first-rounder Mick Abel round out a package that mirrors the kind of multi-premium return Pittsburgh would require to even entertain a Skenes trade.
The catch? The Phillies already boast MLB’s best rotation by WAR and have no pressing need for pitching. But with Dave Dombrowski at the helm, nothing can be ruled out.
Despite rumblings, it looks like Paul Skenes will not be traded by Pittsburgh per @JonHeyman pic.twitter.com/RJkzg7WiSA
— FOX Sports: MLB (@MLBONFOX) May 21, 2025
2. Orioles Pitch a Star-Studded Prospect Package
To Orioles: RHP Paul Skenes
To Pirates: RHP Grayson Rodriguez, C Samuel Basallo, 3B/1B Coby Mayo
Baltimore’s rotation is a mess, and Skenes could be the ace they sorely need. The Orioles have the prospect capital to make it happen. Basallo and Mayo both rank inside MLB Pipeline’s top 20 prospects, while Rodriguez is a recent top-tier pitching prospect still under team control.
This package might actually be the most balanced for Pittsburgh—high-end position players plus a potential frontline starter. It could be tough for the Bucs to turn down if they truly shift toward a rebuild.
3. Red Sox Dangle Baseball’s No. 1 Prospect
To Red Sox: RHP Paul Skenes
To Pirates: OF Roman Anthony, SS Franklin Arias, RHP Luis Perales
This is the most headline-worthy offer yet. Roman Anthony is widely considered the top prospect in baseball right now, tearing up Triple-A. Pair him with two more top-five Red Sox prospects, and Pittsburgh could walk away with one of the most talent-rich hauls in recent memory.
For Boston, it’s a risky all-in play—but one that could anchor the rotation with Skenes and Garrett Crochet through 2029. It also aligns with their current need: everyone in the rotation not named Crochet has an ERA over 5.00.
While Pirates leadership insists Skenes isn’t going anywhere, their 2025 collapse has already started whispers. The right-hander remains under control through 2029, but as history has shown—from Gerrit Cole to Tyler Glasnow—the end often comes sooner in Pittsburgh.
The only question left: who will blow them away first?
Photo Credit: Brad Penner-Imagn Images
