Cubs Face Extra Obstacle in Potential Bid to Acquire Paul Skenes From Pirates

The Chicago Cubs would have their work cut out for them acquiring Paul Skenes from the Pittsburgh Pirates.

May 1, 2025; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates starting pitcher Paul Skenes (30) delivers a pitch against the Chicago Cubs during the first inning at PNC Park. | Charles LeClaire-Imagn Images

Chicago Cubs fans ears perked up with the recent discussions surrounding the potential of the Pittsburgh Pirates to trade away their superstar starting pitcher, Paul Skenes.

The reigning National League Rookie of the Year has gotten off to a historic start in his career, already starting the All-Star Game during his memorable first season as a Big Leaguer.

The Cubs have seen firsthand just how dominant Skenes can be, facing off against him five times, which is more than any other team in baseball.

Their success has been fleeting, with the righty going 2-1 with a 2.88 ERA across 25 innings, striking out 32. Chicago has managed a .215/.311/.366 slash line in 106 plate appearances against him.

Given how talented Skenes is, he would immediately improve every team in the league. However, a team with the pitching situation that the Cubs have should be even more aggressive in pursuing him should he be made available.

Chicago also has the organizational depth that would likely get the Pirates to the negotiating table, capable of offering a ton of young positional players with immense upside.

Pittsburgh has shown little ability to develop hitters drafted in recent years, so it could be appealing to acquire prospects who are close to being MLB-ready and developed in the Cubs’ system.

Cubs Would Have To Pay Even More Than Most Teams for Paul Skenes

There are plenty to choose from — third baseman Matt Shaw, who has made his Big League debut this year but the results haven’t followed yet.

Outfielders Owen Caissie and Kevin Alcantara, catcher/first baseman Moises Ballesteros, and middle infielder Jefferson Rojas could all be of interest to a Pirates team lacking impact hitters at every level.

However, there is one major obstacle that Chicago would have to overcome that other trade suitors won’t — they play in the National League Central against Pittsburgh.

It is hard to envision the Pirates trading away a generational talent and then having to face off against him regularly over the next four years, at minimum.

There could be an NL Central tax on the Cubs, requiring them to pay even more on top of what would already be an astronomical asking price to stay in the race to acquire Skenes.

Pittsburgh fans would be on the verge of mutiny if their only star was traded to a division rival and they didn’t get back everything, including the kitchen sink, in a trade package.

Luckily for Chicago, they have the minor league depth to address their most pressing need at the Major League level. Skenes would make them bona fide contenders with their current lack of starting pitching.