1. Mike Riley
- Years coached: 1999-2001
- Record: 14-34
It was not all Mike Riley’s fault that he had the worst season in franchise history and almost became the first team to go winless before the Detroit Lions eventually would several years later. There are several factors playing into why the Chargers were so bad during this time.
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First of all, the team was coming off of Gilbride’s tenure as head coach where the team could not score the football, prompting upper management to trade up in the draft to select Ryan Leaf, who infamously became one of the worst busts in NFL Draft history.
Riley also had to deal with a massive distraction in Leaf. The 1999 season was actually a good one for the Chargers and a promising one for Riley as the team went 8-8. They were not great in any areas, but with the promise of Leaf still being there (as he did not play in 1999), there was optimism.
That optimism went down the drain the following year as Riley’s Chargers only went 1-15 with the entire season being dominated by a quarterback situation that was headlined by a notoriously bad teammate in Leaf.
Things got better the following year but still were not good as the Chargers went 5-11. This was enough to get the plug pulled on Riley and the Chargers ended up being the only NFL team that he would be the head coach for.
Riley coached the Oregon State Beavers from 2003 to 2014 and that is probably what he will be best remembered for.
However, his tenure with the Chargers was just as bad as it was hilarious to watch, of course, if you ere on the outside watching everything unfold.