The Skenes Conundrum

Paul Skenes, the Pirates' 22-year-old sensation and 2023 No. 1 overall pick, has become baseball's most sought-after pitching asset. With a 98-mph fastball and a devastating slider that induces a 65% swing-and-miss rate, he has already cemented himself as a frontline starter in the majors. His strong start to the 2025 Season (3.44 ERA, 0.82 WHIP in 18.1 innings) underscores his value, especially with four-plus years of team control remaining. Despite Chicago's aggressive pursuit, Pittsburgh shows no urgency to trade its cornerstone pitcher—particularly to a division rival.

Trade Math: Prospects vs. Reality

Pittsburgh's asking price for Skenes is reportedly steep: top Cubs prospects like third baseman Matt Shaw (No. 1 in Chicago's system), right-hander Cade Horton (No. 2), and outfielder Kevin Alcántara (No. 5) are all reportedly on the table. While Chicago's farm system ranks among MLB's deepest, surrendering these blue-chip prospects risks long-term damage. The "NL Central Tax" further complicates matters—the Pirates, trailing in the division standings, would demand a premium to strengthen a rival.

Navigating Divisional Politics

"Pittsburgh would need to be blown away to trade Skenes to Chicago. They’d rather send him to an AL team and avoid helping a competitor." — MLB Analyst

Cubs' Farm Depth: A Double-Edged Sword

Chicago's prospects could theoretically satisfy Pittsburgh's demands: Shaw’s positional Versatility addresses Pittsburgh's third-base needs, while Alcántara’s all-around tools (compared to Mookie Betts) could revitalize the Pirates' offense. However, trading these talents for a "rental" (even with team control) raises sustainability concerns. As one scout noted:

"Shaw and Horton are franchise-building pieces. This trade is a high-risk gamble." — MLB Scout

The Alternatives: A Pessimistic Outlook

Analysts suggest the Cubs might pivot to alternatives like re-signing Shota Imanaga or targeting lower-cost starters such as Frankie Montas. Creative three-team trades could also dilute divisional ties. Yet with Skenes' value peaking, these options may fail to close the gap. The Pirates, holding all leverage, demand maximum return:

"This is a seller’s market, and Skenes is the crown jewel. The Cubs might have to overpay—and even then, it might not be enough." — MLB Executive

Conclusion

As Chicago’s championship window narrows, acquiring Skenes could transform their rotation. But the Pirates’ terms and strategic priorities present insurmountable barriers. For now, the Cubs’ pursuit remains a cautionary tale of short-term ambition clashing with long-term survival.

Keywords: Paul Skenes, Chicago Cubs, Trade Projection