The Seattle SuperSonics Sign Vin Baker (1999)

As if their decision to sign Jim McIlvane — and trade away Shawn Kemp — wasn’t bad enough, Seattle made another critical mistake, signing forward Vin Baker to a seven-year deal worth just under $87 million (after he previously arrived via the trade that sent Kemp to Cleveland).

After Baker arrived in Seattle, his once promising career began to decline rapidly, thanks to substance abuse issues off the court. While his tenure in Seattle was a disaster, things would only continue to get worse for Baker as his career progressed; at one point in time, he tipped the scales at over 300lbs.