The Chargers' quarterback situation in the early-2000s is worth a documentary. It started with one of the biggest busts in NFL history in Ryan Leaf but then continued with big names and future Hall of Famers.
The Bolts drafted Drew Brees with the first pick of the second round in the 2001 NFL Draft and he battled for playing time with over-40 quarterback and CFL legend Doug Flutie. Then, of course, three years later the Chargers drafted Eli Manning, traded him for Philip Rivers, and kickstarted a new era in 2006.
Perhaps the biggest goof that the Chargers made was giving Flutie so much runway to play and not simply trusting in their young quarterback in Brees. Brees did not get to start his rookie season, was named the starter in his second season, and then was eventually replaced in the middle of his third season.
From a long-term perspective it makes no sense to replace your young quarterback with potential with a guy in his 40s who, quite frankly, was not a good quarterback anymore. Brees eventually regained the starting quarterback role but it set the Chargers back.
Finally, with Flutie gone and Philip Rivers in town, Brees was given the starting quarterback role in 2004 and he thrived, leading the Chargers to a 12-4 record. The rest is history. Brees would tear his labrum in 2005, opening the door for Philip Rivers to take over and become the best quarterback in franchise history.