Red Sox, Cubs Entered Last-Second Cy Young Winner Sweepstakes

The Red Sox and Cubs reportedly tried to get deals done...

Feb 27, 2024; Mesa, Arizona, USA; General view of a Chicago Cubs glove, hat and glasses in the first inning against the Cincinnati Reds during a spring training game at Sloan Park. Mandatory Credit: Matt Kartozian-Imagn Images | Matt Kartozian-Imagn Images

The Boston Red Sox were all over starting pitching ahead of the 2025 Major League Baseball trade deadline.

Boston ended up with Dustin May, but he isn't the only starter the Red Sox pursued. Joe Ryan of the Minnesota Twins was the guy who was talked about the most when it came to Boston. But, Jon Heyman of the New York Post reported that the Red Sox and Chicago Cubs were the "most active" teams in the Sandy Alcántara sweepstakes.

"With the (New York Yankees), they asked for one of their top two prospects: Spencer Jones or George Lombard Jr. George Lombard Jr. who is from Miami, so that would've been nice for them. Yankees did not want to trade either of those guys. It did feel like Boston and the Cubs were the most active there. I don't think anyone came close."

Alcántara's name has been mentioned in regard to Boston, but not at the same level that Ryan has. If the Red Sox had landed Alcántara, that would've been a fun move. He's a high-upside guy with a Cy Young Award under his belt. But, he also has severe question marks attached to him. Through 22 starts this season, Alcántara has a 6.44 ERA.

It's not shocking that Alcántara has some rust. He missed the 2024 season after undergoing Tommy John surgery. He has shown flashes of his old self this season and would've been an interesting guy to pair with Garrett Crochet, but it sounds like Miami was asking for too much at this time.