MLB Insider Proposes Chicago Cubs Trade Star Prospects for Cy Young Winner

The Chicago Cubs still have six weeks until the MLB trade deadline, and that’s plenty of time to ponder what the best fits are for their starting rotation.

Despite boasting one of the top records in baseball and a trajectory to the postseason, the Cubs can’t just focus on getting there. To be true contenders, they must address the obvious: the starting rotation.

There will be plenty of sellers with pitchers at the July 31 deadline, but Chicago needs to dominate the market if they want to win games in October.

More News: Former MLB Exec Lists Rangers Ace As Potential Cubs Trade Target Ahead of Deadline

The blockbuster trade by the San Francisco Giants for Boston Red Sox DH Rafael Devers was a jolt to the baseball world, and it ripped the bandage off of the first big move.

The trade demonstrated the willingness of contenders to address a pressing need, and the Cubs must incorporate this blueprint into a package that rivals Devers'.

Jim Bowden of The Athletic (subscription required) recently proposed a trade for Miami Marlins ace Sandy Alcantara to solidify that rotation.

More News: Ian Happ Walks It Off As Cubs Keep Rolling With Another Series Win

In exchange, Chicago would send off top prospects, three of whom are in the MLB Pipeline Top 100: No. 32 right-handed pitcher Cade Horton, No. 45 outfielder Owen Caissie, and No. 69 outfielder Kevin Alcantara. Bowden also included the Cubs' No. 13 prospect, shortstop Ronny Cruz.

Alcantara has emerged as the next headliner of the trade deadline after showing desperately needed signs of a turnaround following Tommy John surgery that sidelined him all of 2024.

From the start of his 2025 campaign through May, Alcantara carried a brutal 8.47 ERA that all but took him off the trade board.

More News: Chicago Cubs Monitoring Health Status of Important Trio of Stars

In his three starts through June 17, Alcantara has a team-best 2.12 ERA and has allowed two runs or fewer in each contest. He allowed no less than five in his four May starts.

Should he show staying power in his return to Cy Young Award-winning form, Bowden thinks he’ll be the acquisition of the deadline.

“In that scenario, adding an ace like Alcantara to their starting rotation would solidify the Cubs’ chances to not only win the NL Central but also vastly improve their postseason odds and chances of advancing to the World Series,” Bowden wrote.

More News: Pittsburgh Pirates Could Satisfy Chicago Cubs’ Pitching Needs at Trade Deadline

The proposal would send 23-year-old Horton to the Marlins to replace Alcantara and two presumably major-league-ready outfielders by next season in Caissie and Alcantara, giving Miami the freedom to potentially trade their outfielders at the deadline.

Caissie has an .879 OPS this year in Triple-A Iowa, and his teammate Alcantara is slashing 239/.322/.400 with seven homers and nine stolen bases. The young 18-year-old Cruz would round out the package.

It’s a steep package—certainly more than the haul the Giants sent for Devers. But this isn’t a disgruntled situation that will downplay Alcantara’s value in a similar fashion.

If Alcantara is truly finding his command and form back, it’s an opportunity Chicago can’t afford to pass up.

For more Cubs news, head over to Cubs On SI.