1. Ryan Leaf trade up
There is no draft pick in Chargers history that is worse than selecting Ryan Leaf with the second overall pick in the 1998 NFL Draft and what makes this draft bust even worse is the fact that the Chargers traded up for Leaf.
It would have been one thing if the Chargers already had the second overall pick and simply got a dud with the second pick. While revisionist history isn't kind to Leaf, there were legitimate discussions around him vs. Peyton Manning heading into the 1998 NFL Draft.
But no, the Chargers did not have the second overall pick in the 1998 NFL Draft. The Chargers had the third overall pick in the draft and wanted to draft Leaf so bad that they paid up to swap spots with the Arizona Cardinals.
The Cardinals, who obviously did not want Leaf to begin with, got a pretty penny and got to draft the person they originally wanted. That pick was Andre Wadsworth, who was not great, but is better than Leaf.
On top of the third-overall pick, the Chargers traded their third-round pick in that draft as well as their first-round pick the following year (ended up being ninth overall). Patrick Sapp and Eric Metcalf were also sent to Arizona.
You know how the story goes with Leaf from that point on.