Deadline Blunders: A Decade of MLB Trade-Deadline Regrets

A look at Sports Illustrated’s ranking of the 10 biggest MLB trade-deadline mistakes from 2016–2026, arguing that deadline moves can haunt a franchise long after the dust settles. The piece flags notable deals such as Cincinnati’s Castillo sell, Cubs’ Quintana swap for Cease and Jimenez, the Dodgers’ Álvarez-for-Fields swap, Padres’ Soto and Tatis-related moves, and the Mets’ Crow-Armstrong-for-Báez trade, among others, ordered 10 through 1 to illustrate how some deadline decisions ruined long-term value or playoff chances while others paid off in surprising ways.