5. Scottie Pippen
Scottie Pippen is unequivocally one of the greatest small forwards of all time, and helped Michael Jordan and the Chicago Bulls capture six NBA titles. Pippen was a tenacious defender and even led the Bulls to the postseason when Jordan retired from the sport.
Pippen made seven All-Star teams, seven All-NBA teams, and 10 All-Defensive teams. Michael Jordan even admitted that he wouldn't have been the legend he is were it not for Pippen.
However, by Pippen's 11th season, he was unable to fetch a contract of his liking, as Bulls owner Jerry Reinsdorf was unwilling to re-negotiate his deal. The Rockets landed the Hall of Famer in 1999, giving him a five-year deal worth upto $82 million.
Pippen joined the team too late, as he averaged 14.5 points (career-low), 43.2 percent from the floor (career-low), 6.5 rebounds, and 5.9 assists and was dealt just one year after being acquired by Rockets GM Carroll Dawson.