Paul Skenes trade grades for ex-MLB GM's Cubs-Pirates hypothetical
Paul Skenes broke onto the scene in 2024 when the Pittsburgh Pirates brought him up to the major leagues in 2024. He went 11-3 en route to starting in the All-Star game, making Skenes the first Pirates pitcher to do so in 50 years. In 2025, Skenes has shone as an individual, but the team around him has faltered. The Cubs could be a dark horse team to entice Pittsburgh to give him up this summer.
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Former Major League Baseball general manager Jim Bowden put together deals from every team for Skenes, and the Chicago Cubs' package features top prospects like Matt Shaw and Cade Horton. Almost every potential deal for the 23-year-old would require a team's best young players. The Cubs are one of the more interesting packages in the league; their top two prospects are already playing in the majors.
Skenes and the Pirates have been fighting trade rumors since they started after the team's slow start. However, experts like Bowden continue to explore the possibilities. According to him, the Chicago Cubs' players provide the most immediate upgrades to the Pittsburgh.
Proposed package: RHP Cade Horton, 3B Matt Shaw, OF Kevin Alcántara, SS Juan Tomas
'The Pirates would acquire Horton, the Cubs' top pitching prospect, who could immediately go into their rotation, and he'd come with an extra year of control than they have with Skenes,' Bowden. 'Shaw could be moved to second base. Alcántara could be promoted to the majors to play left field, and he'd be an instant upgrade in the Pirates' lineup. Tomas, 17, is a solid prospect who could develop into their long-term solution at shortstop. Meanwhile, Skenes would make the first-place Cubs a real October threat.'
Why the Chicago Cubs should make the trade
Adding Skenes would take teams from the fringe of contention to serious World Series consideration. The Cubs' rotation is led by Shota Imanaga, who would be in All-Star consideration if he wasn't on Chicago's injury list. Behind him, Matthew Boyd and Jameson Taillon have been serviceable, but Craig Counsell is in need of a second star. Skenes fills that hole emphatically and could be the team's ace for the next decade if they can keep him in a Cubs uniform.
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Both Imanaga and Skenes have ERAs less than 2.90. If they joined forces, they would be one of best pitching duos the league has to offer. For a team that is always done in by their pitching in the postseason, bringing in the young ace would give the Cubs peace of mind in tense playoff matchups. Skenes has yet to pitch in the playoffs, but odds of him translating poorly from the regular season to the playoffs are slim considering just how dominant he has been so far in his career.
Shaw and Horton recently made their MLB debuts for Chicago and have impressed so far. Giving them up leaves some immediate holes in the Cubs' roster, but it is well worth the price to bring in Skenes. However, losing both of them, along with two promising prospects still in the minor leagues is enough to give Chicago's front office a reason to step back and look at the deal closely.
Many of the Cubs' concerns would go away if they sign Pete Crow-Armstrong to a long-term deal. Doing so would secure their star of the future and allow them to be more aggressive. The move guts the top of their farm system, but Chicago is capable of developing talent as well as most other teams in the league.
Cubs Trade Grade: B+
Why the Pittsburgh Pirates should make the trade
Oneil Cruz, Bryan Reynolds, and Ke'Bryan Hayes are the leaders of the Pittsburgh Pirates' offense. However, Cruz and Skenes have both been thrown out as potential trade candidates. The future of the Pirates cannot be carried by just their ace, no matter how good he is. For that reason, Pittsburgh could make the tough call to bring in a variety of players instead of putting all their hopes into one.
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The Pirates moved on from Derek Shelton, a sign that more changes are coming. Things around Pittsburgh are in a state of flux, including the roster. However, losing so many games makes it difficult for the organization to determine which players are worth keeping. Because of that, the Pirates could chose to stand still at the deadline. If they do make a deal, they need to make sure it is the right one for their future.
Pittsburgh needs a miraculous turnaround to return to contention. Despite losing so many games, fans expect improvement from a roster that surprised the league in the second half of last season. Bringing in prospects would definitely give the team a different look.
Horton would immediately have a spot in the rotation. Straw would move from third base, but the Pirates' infield is in need of an upgrade as well. Alcántara is a bigger question mark. With Andrew McCutchen mentoring him, though, he could turn into an asset in the field.
The Pirates struck gold when they picked Skenes in the 2023 draft. However, if they team can't pay him what he will want in free agency, the best move could be a trade. The Cubs give them players to build around, but it is a tough sell to their fans. However, big risks are necessary for the Pirates to eventually get over the hump.
Pirates Trade Grade: B
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