Red Sox Targeting Stud Starter Who 'Has A History' With Craig Breslow

Boston might have an advantage over other suitors in pursuit of a certain Cubs pitcher

Feb 13, 2019; Mesa, AZ, USA; Chicago Cubs manager Joe Maddon (right) talks with director of strategic initiatives Craig Breslow during a spring training workout at Sloan Park. Mandatory Credit: Matt Kartozian-USA TODAY Sports / Matt Kartozian-USA TODAY Sports

The Boston Red Sox will be jockeying on the trade market for a talented starting pitcher over the next five days.

In seeking a competitive edge, the Red Sox might discover that trading with the Chicago Cubs presents a unique opportunity that other teams are not granted.

Boston’s chief baseball officer Craig Breslow worked for the Cubs in the years before Breslow was hired by the Red Sox in October 2023. As such, Breslow is ultra familiar with the Cubs organization and Chicago’s roster.

One Cubs player with whom Breslow has a notable connection is Jameson Taillon. Conveniently, Taillon has been linked to the Red Sox in recent days; he’d be an excellent addition to Boston’s understaffed pitching rotation.

As Taillon’s various suitors (Boston included) line up to prepare offers, the Red Sox could have the upper hand in negotiations based on Breslow’s familiarity with Taillon.

The Athletic’s Jen McCaffrey reported on this advantage on Wednesday.

“As far as the Taillon rumor, that one piqued my interest, particularly because chief baseball officer Craig Breslow has a history with Taillon,” McCaffrey said. “When Breslow was hired by the Cubs, Breslow put together a detailed pitch to Taillon when he was a free agent in 2021, and the Cubs signed him to a four-year, $68 million deal. Taillon, 32, has two years left on the deal and has a 3.10 ERA in 16 starts this season. Breslow has a good idea of what the Cubs would want in return, and adding Taillon could be one way to stabilize the rotation.”

Acquiring Taillon would be an enormous win for Breslow, to the point where even if Breslow struck out on other deadline deals, fans would be satisfied on the whole with his deadline performance.

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