1. Drew Brees
Drew Brees is the figurehead for this list. Not only is Brees the best example of someone the Los Angeles Chargers drafted that went on to have a great career elsewhere, but he might also be the example for the entire league of this being the case.
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Brees is going to go down as one of the greatest quarterbacks of all-time and rightfully belongs in the top-five. He holds multiple all-time records, has won a Super Bowl and did it all away from the Chargers in New Orleans.
No other legendary quarterback has the same story. Peyton Manning, despite signing with the Broncos, is still a lifetime Colt. Tom Brady defines the New England Patriots, Dan Marino with the Jets, Brett Favre with the Packers.
Sure, some of the all-time greats will find a new home later in their careers, but this is not the case. The Chargers essentially gave up on Brees, and while transitioning to Philip Rivers was not a bad thing in the slightest, Brees went on to be a legend.
He was a Pro Bowler just once in San Diego but then went on to be an All-Pro in his first season with the Saints. That was a telling sign for a Saints career that would include 12 Pro Bowls, two offensive players of the year and 65,058 (so far) passing yards.
Outside of 2019, where Brees missed five games, his worst season in terms of passing yards for the Saints is still more than his best season with the Chargers.
All we can do is look back and say what-if. What if the Chargers committed to Brees long-term and instead used the first overall pick in the 2004 NFL Draft on someone such as Larry Fitzgerald.