The Chicago White Sox are engaging in one of the largest rebuilding efforts in Major League Baseball history and could land a few big pieces by pulling off a swap with an American League East contender.

Just about anyone with knowledge of Chicago’s plight believes that the White Sox will deal away staff ace Garrett Crochet this winter. It will be a massive transaction, as Chicago needs to land at least two — if not three— future difference-makers for one of the team’s few remaining trade chips.

To that end, Jim Bowden of The Athletic envisions a deal that sends Crochet to the Boston Red Sox for a package of first baseman Triston Casas, outfielder Wilyer Abreu, and catcher/utilityman Connor Wong.

That proposed deal would land the White Sox the third-place finisher in the 2023 American League Rookie of the Year voting (Casas) as well as last season’s six-place ROY finisher and a Gold Glove Award winner (Abreu). 

While Chicago would give up its No. 1 starting pitcher, the team would receive two players that could star on the south side of the Windy City for at least the remainder of the decade. Casas is not eligible for free agency until 2029, and Abreu is not eligible until 2030.

Casas, 24, missed the majority of the 2024 campaign due to torn cartilage in his rib cage but returned in mid-August. He hit 13 home runs in 63 games after launching 24 homers in 132 games during his rookie season in 2023.

Abreu, 25, was impressive in his rookie year, finishing 2024 with a .253 average to go with 15 homers, 58 RBI, 59 runs scored, and splendid defensive work in right field at Fenway Park.

Wong is the “old man” of the trio at 28 years old. He is a catcher by trade but played all over the field for Boston over the past three seasons. He hit a career-best .280 in 126 games last season, hitting 13 homers with 52 RBI.

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