Ryan Leaf

In the 1998 NFL draft, the San Diego Chargers wanted Ryan Leaf so badly they traded three draft picks and two players for a chance to sign the college star from Washington State. While it’s hard to believe now, analysts debated whether Leaf deserved to go as No. 1 in the draft ahead of another quarterback, by the name of Peyton Manning. Leaf’s contract—$31.5 million for four years, with a then-record $11.25 million signing bonus—is widely considered one of the worst contract decisions in pro sports. After a middling rookie season, Leaf suffered a severe shoulder injury in 1999 and missed the entire season. Chronic pain led to an addiction to painkillers. All the while, Leaf continued to alienate teammates, coaches, and fans. His work ethic was ridiculed as he was often seen golfing when his team was working. San Diego released Leaf after the 2000 season, and he failed to mount comebacks in briefs stints with Tampa Bay and Dallas. In his four NFL seasons, Leaf threw for 14 touchdowns and 36 interceptions, with a passer rating of 50 percent. In June 2012, Leaf received a seven-year prison sentence after being convicted of burglarizing a home in Montana and possessing drugs.

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