Back when the Los Angeles Chargers were known as the San Diego Chargers, they made a move from the third pick to the second pick in the 1998 NFL Draft to ensure they got one of the two top prospects that year (both happened to be quarterbacks, which the Chargers needed).
One was a guy named Peyton Manning, someone Chargers fans would come to know too well, as he eventually found his way into the AFC West and tormented them for several years. The other quarterback's name was Ryan Leaf, who also tormented Chargers fans for years but did so while playing for the team.
With the Colts holding the top pick in the draft, the Chargers didn't really get a say in who they were taking that year. They took the guy the Colts didn't want and since the Colts wanted Manning, the Chargers selected Leaf. For what it's worth, draft experts seemed convinced that both Manning and Leaf would turn into successful starters for whichever team took them.
That didn't turn out to be true at all. The Leaf selection did not pan out for the Chargers and he's widely known as the biggest bust in NFL history.
Why Ryan Leaf is the worst draft pick in Chargers history
The red flags were being waved even before Leaf had been drafted, such as his arrogance and not showing up to interviews. Once he officially became a Charger, Leaf celebrated by flying out to Las Vegas and yawning his introductory press conference the next day. The writing appeared to be on the wall before Leaf ever even took a snap.
While the Chargers won their first two games of the (short-lived) Leaf era, he didn't play well. It was his third start, one against the Chiefs, that really led to things unraveling. Leaf went 1-of-15 for four yards and two interceptions while losing three fumbles in an eventual 23-7 loss to Kansas City. The train was officially off the tracks, as Leaf later shouted at a local reporter in the locker room to "knock it off".
Leaf's play didn't improve even after that dreadful outing against the Chiefs. He threw four picks the next week against the Giants, and, after throwing the first touchdown pass of his career in Week 1, didn't throw another one until Week 8. That was his final touchdown pass of his brutal rookie season, giving him two total touchdowns versus 15 interceptions in 10 games.
He missed the entire 1999 season due to a shoulder injury and Chargers fans were trying to be optimistic about Leaf rebounding when he returned in 2000. Those hopes were dashed pretty quickly as he threw three picks in the first game of the 2000 season. While he did increase his touchdown numbers that year (11), turnovers continued to be a problem, as he threw 18 interceptions in 11 games.
It was clear when the 2000 season came to a close that Leaf was not going to be the guy in San Diego. The Chargers went 1-15 that year and held the top pick in the upcoming draft. They didn't end up staying in that top spot but still parted ways with Leaf, releasing him and officially putting an end to an era that Chargers fans wish they could forget.
Leaf tried comebacks with the Buccaneers, Cowboys, and Seahawks but only played sparingly with the Cowboys in 2001. When it was clear that he was not going to be the quarterback everyone thought he'd be, there wasn't anywhere left for him to attempt a comeback in the NFL.
The good news is that the Chargers selected Drew Brees in the second round of the 2001 NFL Draft, who played for them for five years before Philip Rivers took over for the next 14 years, and now Justin Herbert has been next in line for quarterback consistency. So while the Leaf pick was bad, the Chargers have since shown that they know how to draft and develop quarterbacks.