18. Ray Allen to the Sonics
Trade: Milwaukee Bucks get Desmond Mason and Gary Payton; Seattle Supersonics get Ray Allen, Ronald Murray, Kevin Ollie and a 2003 1st Round Draft pick (Luke Ridnour).
This is a story of how trading two stars for each other doesn't always work out. Gary Payton was in the last year of his contract (and in the twilight of his career) when he was traded to Milwaukee. In free agency, he decided to join Karl Malone to form the "Super" Lakers. Since this trade, Milwaukee has never moved past the first round of the playoffs. Seattle didn't fare much better either, and they had Ray Allen for over four years. Outside of one random great season in 2005, Seattle never made the playoffs, eventually trading Allen to Boston in 2007. And GP had to follow the ring to Miami.