A Red Sox-Cubs trade to reunite Craig Breslow with previous free agent darling

The Boston Red Sox, behind a breakout season from Jarren Duran among others, have placed themselves in prime position to be buyers this year. One place that they need to upgrade before the upcoming trade deadline is the back end of their pitching staff.

MLB insider Bob Nightengale agrees, and he mentioned a few intriguing names as pieces the Red Sox could go after. Nightengale mentioned Chicago Cubs starter Jameson Taillon and Chicago White Sox starter Erick Fedde as two guys that Boston could pursue.

Taillon makes the most sense, largely because Red Sox GM Craig Breslow, played a large role in recruiting Taillon to the Cubs a few seasons ago. Now with Breslow in charge in Boston, he could look to reunite with his old friend Taillon.

670 The Score baseball analyst Bruce Levine also reported that Taillon will be available before the deadline, if teams are pursuing him.

A Red Sox-Cubs trade to make Craig Breslow a happy man

Taillon, 32, would come with two additional years of team control following this season, making him one of the safer options for buying teams at the deadline. He currently holds a 3.10 ERA and a 1.16 WHIP across 93 innings.

The Cubs would likely have to eat a chunk of his contract in order to deal him for the value that he's worth, which wouldn't kill them to do either way. It would be smart for both sides if Chicago eats a bit of the deal and Boston coughs up a bit better prospects.

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.

Wikelman Gonzalez, the Red Sox fifth-ranked prospect, has an electric arsenal but erratic control. His talent is incredible, but his inconsistency has led to an ERA near 7.00 this year. With Boston going pitcher-heavy in the early rounds of the draft, they can afford to lose their top farm system arm. The Cubs would be buying low on this electric prospect.

Allan Castro is also expendable to the Red Sox. Boston went outfield-heavy early on in the draft as well, making their second-highest-ranked outfielder somebody that can be dealt. He's slashing a respectable .239/.365/.434, good for an OPS near .800.

Boston would be losing out on two prospects that they recently replaced in their farm system with the draft while adding in a pitcher that can help them win. A pitcher that their GM likes a lot.