Chris Webber for Penny Hardaway (1993)

The Chris Webber-for-Penny Hardaway swap ranks as one of the most lopsided trades in NBA history. After just one season, the Golden State Warriors dealt the 1993 Rookie of the Year to Washington for Hardaway and three first-round picks, but then immediately flipped those picks to Orlando for Anfernee Hardaway—a player who had yet to suit up for the Magic. Hardaway went on to average 20.9 points and 7.2 assists over his first three seasons with Orlando, helping the team reach the 1995 NBA Finals. Meanwhile, Webber never played a game for Washington, demanding a trade within months and landing with Sacramento, where he became a five-time All-Star.