Players Most Valued or Traded at MLB Deadlines

Exploring players who have been frequently traded, top prospects involved in deadline deals, and those who significantly boosted their trade value just before the deadline.

The top 3

1. Top 3 Players Traded Most Times in MLB History: Dick Littlefield and Willie Montanez share the record, each being traded 8 times during their careers, while Jesse Chavez has been traded 7 times, with 4 of those occurring at the trade deadline.
2. Highest Ranked Prospects Traded at Deadline Who Became Stars: Yoán Moncada, the No. 1 prospect in 2016, was traded from the Red Sox to the White Sox for Chris Sale; Leo De Vries, the No. 3 prospect in 2025, was traded from the Padres to the A's; and Eloy Jiménez, the No. 8 prospect in 2017, was traded from the White Sox to the Cubs.
3. Players Who Boosted Their Value Most Right Before Deadline: Sandy Alcantara significantly increased his trade value in 2026 by delivering three consecutive quality starts, Byron Buxton was 'scorching hot' with a 1.064 OPS and 16 homers in 35 games, and Lane Thomas boosted his stock with 7 homers and an .814 OPS in 40 games before the 2026 deadline.

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