Chicago Cubs President of Baseball Operations Theo Epstein hasn’t been shy about trading big pieces. In 2004 he moved Nomar Garciaparra, a fan favorite in Boston and at that time seen as a key piece. In return, the Red Sox received shortstop Orlando Cabrera and first baseman Doug Mientkiewicz.
The deal happened right at the trade deadline. Garciaparra was a mutli-Gold Glove winner and at the time of the trade was slashing .321/.367/.500 with an .867 OPS. It was a shocking move, but the Red Sox went on to win the World Series that year.