Insider Urges Red Sox To Consider Cutting Ties With Struggling $90 Million Slugger

Can the Red Sox move on from this big-money contract?

Feb 18, 2019; Lee County, FL, USA; A general view of a Boston Red Sox helmet as Boston Red Sox center fielder Jackie Bradley Jr. (19) walks on the field during a spring training workout at Jet Blue Park at Fenway South. Mandatory Credit: Jasen Vinlove-Imagn Images / Jasen Vinlove-Imagn Images

The Boston Red Sox have some tricky puzzle pieces to fit together this winter, and unfortunately, one existing piece is extra difficult to place.

Two years ago, the Red Sox inked Japanese slugger Mastataka Yoshida to a five-year, $90 million contract to be their everyday left fielder. Two years into the deal, however, Yoshida has already become a full-time designated hitter due to his defensive shortcomings, and he hasn't been as good as advertised with the bat, either.

The Red Sox are kicking around all sorts of plans this winter, namely moving third baseman Rafael Devers either to first base, where Triston Casas currently resides, or to Yoshida's DH slot. That has made Casas a popular trade candidate in hypothetical deals this winter.

The Red Sox could also look to deal Yoshida, but his contract makes it difficult to find an interested party. However, one insider believes that shouldn't be enough of an impediment.

Recently, John Tomase of NBC Sports Boston urged the Red Sox to set Yoshida's contract aside and make whatever move best suited the team's offensive needs, moving Yoshida in a potential trade over letting go of Casas.

"If Devers moves, dominoes will start falling. He could assume first base duties and make young slugger Triston Casas available in a trade. Breslow sounds understandably disinclined to trade Casas, however, since the youngster boasts 40-homer power and has his entire prime in front of him," Tomase said.

"That means either Devers or Casas could slide over to DH and make incumbent Masataka Yoshida expendable, even though there's three years and more than $50 million remaining on his contract... Yoshida should not be the impediment to a Devers move, and his presence definitely shouldn't contribute to a Casas trade."

Further complicating matters, Yoshida underwent shoulder surgery at the end of September, possibly delaying the start of his 2025 season. The shoulder injury likely also affected his offensive production, so Yoshida is hoping to prove himself once he gets healthy.

Put plainly, Casas is a more valuable hitter than Yoshida at this point, and the Red Sox have to operate based on what will help them win more games. It's always painful to admit defeat on a big investment, but the Red Sox can't let past mistakes lead to future shortcomings.

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