A Red Sox-Cubs trade to steal a starting pitching option from the Yankees

The Boston Red Sox have made up tremendous ground in the American League in July. They've improved their record to 10 games over .500 and currently have over a 60 percent chance to make the postseason, per Baseball Reference.

MLB insider Bob Nightengale has reported that both the Red Sox and their arch rival New York Yankees are interested in making a trade for Chicago Cubs starter Jameson Taillon.

"The Boston Red Sox and Yankees have had talks with the Chicago Cubs about starter Jameson Taillon, but the Cubs are undecided whether they will be buyers or sellers," Nightengale wrote.

The Red Sox and Yankees rivalry could run deeper than just on the field this year, with Boston now having to outdo the Yankees in order to acquire the pitcher they may desperately need.

(For more news and rumors, check out MLB Insider Robert Murray’s work on the Baseball Insiders podcast and join the discord to get the inside scoop as we near the July 30 MLB trade deadline.)

A Red Sox-Cubs trade to steal Jameson Taillon from the Yankees

Taillon, 32, is attached to over $40 million left on his contract over the course of the next two and a half seasons. On the 2024 season, he holds a 3.10 ERA, 1.16 WHIP and a 1.8 WAR over his 16 starts. He's truly been impressive at the top of the Cubs rotation, but with Chicago falling out of contention, they will likely look to deal him, especially in order to get off some of his contract.

Projecting a trade for a player with so much money left on his contract is difficult. The Cubs will likely need to pay some of his salary to move him for the prospect capital that he's worth as a player. But guessing how much or how little they're willing to pay is where it gets complicated. For this hypothetical, let's assume the Cubs are paying half of his remaining salary.

In the deal are Boston's No. 8, 10 and 19 prospects, per MLB Pipeline.

Zanetello, 19, has struggled this season, slashing .207/.327/.371 in Low-A. Still being a teenager, he has plenty of time to grow and develop. His raw tools allow him to be a highly rated and highly coveted prospect.

Fitts, 24, is quite the opposite. He seems to be near MLB ready as he's on the older side of prospect status. He holds a 4.98 ERA in 77.2 innings in 2024. The 6-foot 3 righty has a good fastball/slider combination that he pairs with solid command.

Jordan, 21, is a solid offensive infielder with a .270/.317/.428 slash line in 2024. He's shown a developed approach at the plate this season and he looks to continue growing as he moves up the minor leagues.

With the Yankees showing interest in Taillon too, Boston needs to prioritize adding him or a pitcher of a higher caliber before their rivals pounce on it. Boston doesn't want to look back and regret missing out on a target that the Yankees landed.