Red Sox's trade failures further magnified in recent roster move

The Boston Red Sox dismantled the 2018 World Series winning squad quickly after the trophy was lifted, particularly in the outfield.

Mookie Betts, Jackie Bradley Jr. and Andrew Benintendi were all playing elsewhere by 2021, under the guise of bettering the team.

Now, Boston is holding onto just a few trade pieces from the exchanges for its once-dominant outfield. This weekend, the Red Sox dropped right-handed pitcher, Luis De La Rosa.

De La Rosa was one of the five pieces the Sox got in exchange for sending Benintendi to the Royals in 2021, and he's the third one they no longer have in the organization. Franchy Cordero made 132 big-league appearances for Boston and departed in free agency while outfield prospect Freddy Valdez never made it past the Florida Complex League with the Red Sox.

De La Rosa is coming off an interesting 2023 campaign with Single-A Salem. The 21-year-old posted a 2.94 ERA in 70.1 innings with 88 strikeouts and 40 walks. His ERA was much improved from his 2022 numbers with Salem, although he only pitched 34 innings for the club that year. De La Rosa logged a 4.72 ERA in Single-A, but a 1.26 mark in the Florida Complex League over 14.1 innings.

The Red Sox cut ties with Luis De La Rosa, one of five return players from the Andrew Benintendi trade

It is uncertain why the Red Sox organization is letting De La Rosa go after his 2023 performance, but SoxProspects.com considered him more of a fringe-level prospect with potential as a minor-league depth or organizational arm. The Dominican Republic native converted from a shortstop to a pitcher shortly before signing with the Royals at the age of 16.

Boston cutting ties with De La Rosa leaves it with just two out of five pieces from the Benintendi trade — Josh Winckowski and Grant Gambrell. Winckowski is set to have a bigger role than ever for the Red Sox this coming season, as there are two spots in the starting rotation available to relievers on the team. Gambrell reached Triple-A last season and SoxProspects has him listed as a potential reliever at his highest outcome.

It's hard to know whether Benintendi would still be with the Red Sox had he played out his arbitration years. But it's clear that a lot of Boston's trades for prospects that were designed to better the club for the future haven't panned out.

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