MLB insider Steve Phillips identifies one team that needs to trade for Red Sox Aroldis Chapman

With the MLB trade deadline rapidly approaching, the Boston Red Sox appear to be headed toward selling off some of their most valuable assets. Sitting in last place and well out of contention, the organization is expected to listen to offers for several veterans, with closer Aroldis Chapman likely to generate the most interest.

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One baseball analyst already has a destination in mind. According to MLB insider Steve Phillips, the Chicago White Sox should make Chapman one of their top trade targets before the deadline.

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A Perfect Match for Chicago

Jun 28, 2026; Boston, Massachusetts, USA; Boston Red Sox relief pitcher Aroldis Chapman (44) delivers a pitch during the ninth inning against the New York Yankees at Fenway Park. Mandatory Credit: Paul Rutherford-Imagn Images

The White Sox have been one of the biggest surprises in baseball this season. After entering the year with modest expectations, Chicago has emerged as a legitimate playoff contender and is firmly in the hunt for the American League Central title. While the club has played well on both sides of the ball, adding another elite reliever could be the move that puts it over the top.

That’s where Chapman enters the picture. Even at this stage of his career, the veteran left-hander remains one of baseball’s most intimidating bullpen arms. His experience closing out high-pressure games, including appearances on the World Series stage, would bring immediate credibility to Chicago’s bullpen.

Familiar Trade Partners

Jun 18, 2026; Boston, Massachusetts, USA; Boston Red Sox relief pitcher Aroldis Chapman (44) pitches against the Toronto Blue Jays during the ninth inning at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images

A deal between Boston and Chicago wouldn’t be unprecedented. The two organizations have completed several significant trades over the years. The Red Sox famously acquired Chris Sale from the White Sox in exchange for a package of top prospects, and before the 2025 season, Boston landed Garrett Crochet in another blockbuster that also sent a haul of young talent to Chicago.

This time, however, the roles would be reversed. Instead of Boston buying, it would be the White Sox looking to strengthen a playoff-caliber roster with Aroldis Chapman for the stretch run.

A Move That Makes Sense

Chapman checks nearly every box for a contender searching for bullpen help. He has postseason experience, has thrived in high-leverage situations throughout his career, and gives managers another trusted option to protect late leads.

For a White Sox team trying to compete with the American League’s best, acquiring a proven closer could be one of the most impactful moves available at the deadline.

If Steve Phillips is right, Chicago shouldn’t hesitate. Opportunities to add a reliever with Chapman’s résumé don’t come around often, and with Boston expected to sell, the timing could be perfect for another blockbuster trade between two familiar front offices.

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