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Major Breaking: Chicago Cubs Reunite With Former Cy Young Winner

Posted on April 18, 2025

The Chicago Cubs faced a challenging 2024 season, finishing with an 83-79 record and missing the postseason for the fourth straight year.

While the Chicago Cubs’ starting rotation performed well overall, they struggled with production from the No. 5 spot due to a lack of depth. To address this issue, the team signed Matthew Boyd and Colin Rea during free agency.

Despite strengthening their rotation and reportedly being in talks with free agent Lance Lynn, the Cubs have also been linked to 2022 NL Cy Young Award winner Sandy Alcantara.

Jeff Passan of ESPN recently reported that teams are speculating whether the Miami Marlins will make their ace, Sandy Alcantara, available at the trade deadline.

Zach Rymer of Bleacher Report predicts that Chicago will be one of the teams in the hunt to acquire two-time All-Star Sandy Alcantara. He points out that the Cubs’ interest in Lance Lynn highlights their lack of depth beyond their top three starters.

The Cubs, similar to the Red Sox, have more young hitters than they have space for. Zach Rymer of Bleacher Report suggests that the saying “If you can’t play ’em, trade ’em” should apply here. His trade proposal involves the Chicago Cubs acquiring RHP Sandy Alcantara from the Miami Marlins in exchange for RHP Javier Assad, C Moises Ballesteros (Cubs No. 3, MLB No. 41), and OF Kevin Alcántara (Cubs No. 6). While Assad may be a bit redundant in Chicago, the 27-year-old has proven to be a capable major league pitcher, with a 3.73 ERA over 147 innings last season. The key assets in this trade would be Ballesteros, a high-average hitter, and Alcántara, a player with both power and speed. Neither has a clear path to playing time in Chicago, but both would have an opportunity to contribute in Miami.

Javier Assad made 29 starts for the Cubs last season, recording a 7-6 record, a 3.73 ERA, and 124 strikeouts in 147.0 innings pitched. However, he is currently dealing with an oblique strain and did not pitch during Spring Training.

All three players in the proposed trade—Javier Assad, Moises Ballesteros, and Kevin Alcántara—did not make the Chicago Cubs’ Opening Day roster. They were also not among the 31 players who traveled to Japan for the Tokyo Series.

Meanwhile, Sandy Alcantara has been outstanding during Spring Training after missing all of 2024 due to Tommy John surgery. The two-time All-Star has pitched 12.1 innings, not allowing an earned run, striking out ten batters, and walking just three.

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