Most despised former Chargers: Ryan Leaf
Ryan Leaf might be the most despised player on this entire list as he was a painful reminder of how close the Chargers were to getting a Hall of Fame quarterback. Instead, they got one of the biggest draft busts in NFL history who wasn't very good on the field and had huge issues off the field.
Thankfully, Leaf has appeared to turn his life around and while he is a despised former player, every Chargers fan should be rooting for that to be the case. Leaf now gets to build a personal legacy and leave his Chargers days behind him. The fanbase, however, will never forget how dark those days were.
Leaf was the second overall pick in the 1998 NFL Draft, going just one selection behind future Hall of Famer Peyton Manning. Perhaps Manning would have pulled the same move as his brother but if not, imagine if the Chargers had Manning for those mid-2000s teams instead of Rivers.
Nothing against Philip Rivers, we all love him here at Bolt Beat. But the Chargers would have been multiple-time champions if the Indianapolis Colts somehow screwed that up and took Leaf with the first overall pick.
Leaf lasted just three years with the organization before it eventually cut ties with him. That is more common in today's NFL but back in 2001, the second overall pick getting the ax before the end of his rookie deal really was groundbreaking stuff.