Year: 2008
Contract: 5 years, $80 million

There was a time when this deal would've been a no brainer. Giving him this deal after a ruptured Achilles tendon wasn't the time. The February after signing the deal with Philly, Elton dislocated his shoulder and had season ending surgery. Though he would return, in each year of his contract, his salary was higher than his PPG. The Sixers would eventually amnesty him in 2012.