Proposed Chicago Cubs Trade Would Send Starting Pitcher to Boston Red Sox

A proposed Chicago Cubs trade would get two top 12 prospects back from the Boston Red Sox system.

May 30, 2024; Milwaukee, Wisconsin, USA; Chicago Cubs starting pitcher Jameson Taillon (50) delivers a pitch against the Milwaukee Brewers in the first inning at American Family Field. / Michael McLoone-USA TODAY Sports

The Chicago Cubs had an opportunity out of the All-Star break to show the front office that they're a better team than what was shown in the first half. Instead, they lost the first two games of a three-game set against the Arizona Diamondbacks, and time appears to be running out.

With the July 30 trade deadline almost a week away, the Cubs are in the definition of a do-or-die situation. Any loss at this point of the season essentially kills the chances of them being buyers.

And if they aren't buyers, that could only mean one thing.

Chicago is in a position to sell, and from the look of things, it might be the right decision. It's clear that this team needs plenty of help, and with it being a buyers' market, it's tough to imagine a scenario where they can even improve the roster as much as they need to.

With players to trade, it's time to start thinking about who could bring back a favorable package. According to Bob Nightengale, Jameson Taillon could be one of those players, and he named the Boston Red Sox as a potential landing spot.

Add .@BNightengale to the list of people who expect the Red Sox to be buyers at the trade deadline.

He mentions Jameson Taillon (3.10 ERA/3.81 FIP) and Erick Fedde (2.99 ERA/3.53 FIP) as possibilities.

Breslow was a big part of recruiting Taillon…
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— Tyler Milliken ⚾️ (@tylermilliken_) July 19, 2024

Zach Pressnell of FanSided proposed a deal that has Taillon going to the Red Sox after the rumors. His trade would move Taillon and cash considerations for Wikelman Gonzalez and Allan Castro.

"Let's assume the Cubs are willing to eat about half of Taillon's remaining contract. With that in mind, the prospect capital in the deal is completely dependent on how much of the contract would end up on each side.

"Meaning, that if the Cubs, hypothetically, were to eat the entire deal, they would get significantly more prospects. If the Red Sox had to take the entire contract, they wouldn't have to send as much to Chicago. Let's assume this is in the middle."

Gonzalez is the No. 5 player in Boston's system, while Castro comes in at No. 12, according to MLB Pipeline.

Taillon's four-year, $68 million contract is where things get difficult in a trade for him. He does have another two years on his contract, and the right-hander has proven he can be an above-average arm, so it's not necessarily the worst contract out there.

However, moving an expensive arm does get tough, especially if they aren't elite.

On the season, Taillon has been better than ever before, posting the highest ERA+ of his career at 136. His 3.10 ERA would also be a career best if he keeps it up.

That should interest teams.