Year: 1996
Contract: 7 years, $33 million

Remember the 1996 NBA Finals? When Shawn Kemp arguably outplayed Michael Jordan? That deserves a big payday, right? Duh. For Jim Fucking McIlvaine? Really? Sonics brass decided that locking up ol' Jim was more important than appeasing the Reignman, so they threw big money at the former and traded the latter to Cleveland just a year later. The Sonics never made it past the first round again. Welp. You get what you pay for.