Hakeem Olajuwon, Toronto Raptors, 2001: three years, $17 million

Antonio Davis, Toronto Raptors, 2001: five years, $60 million

Jerome Williams, Toronto Raptors, 2001: seven years, $40.8 million

Alvin Williams, Toronto Raptors, 2001: five years, $35 million

This quartet of ill-fated signings set the Raptors back a half-decade. For $150 million, you'd hope to at least get beyond the first round of the playoffs, but the Raptors won only 42 games in the 2001-02 season and lost to the Pistons in the playoffs. Even with Alvin's recent buyout, the Raptors are still paying for these moves.