The Los Angeles Chargers franchise has had plenty of ups and downs dating back to their time in San Diego, but the worst stretch in franchise history was the pre-LaDainian Tomlinson era of the late 1990s and early 2000s. The combination of bad drafting, coaching, and quarterback play was lethal.
While no coach would have been able to win games with Ryan Leaf as the starting quarterback, the Chargers made a huge mistake when they identified former college coach Mike Riley as the best leader of men they could find.
Even with some heartbreaking losses added to the franchise ledger in the last few seasons thanks to Brandon Staley, Riley remains the worst coach Chargers fans ever had the displeasure of watching.
Mike Riley is the worst coach in Chargers history
Riley has an interesting decade before joining the Chargers. After becoming a head coach in Canada with the Winnipeg Blue Bombers and a stint as USC's offensive coordinator and assistant head coach, the Corvallis native went back home to take the head coach job at Oregon State.
Riley getting hired by the Chargers seemed odd at the time. While the Beavers' program was in the middle of a streak of 28 consecutive losing seasons (which Dennis Erickson would help snap the following season), it seemed odd to hire a coach with an 8-14 record in two seasons to make the jump to the NFL.
The Chargers were banking on Riley's offensive expertise to get the most out of Leaf and his more laid back personality (as compared with the tightly-wound Kevin Gilbride) to turn this team around.
Things started off well after Leaf missed the 1999 season, as a veteran Jim Harbaugh and Top 10 defense were able to carry San Diego to an 8-8 record. Problems came in 2000, as Leaf returned from injury and the defense regressed so hard that they became one of the grossest spectacles the league has ever seen.
The 2000 Chargers are without question one of the worst teams in NFL history. They went 1-15, and the win was by one point on a last-second field goal. Leaf started nine games, Harbaugh had five, and Moses Moreno had two. Those quarterbacks combined for 19 touchdowns and 30 interceptions.
The Chargers were bad enough to end up with Tomlinson and Drew Brees in the same NFL Draft after this season, but Riley chose to lean on ageless wonder Doug Flutie in what would be his final NFL season. Another whimpering offensive showing led the Chargers to a 5-11 record. Riley started the year 5-2, but lost nine straight games. He finished 14-34 as Chargers head coach.
Riley would later return to Oregon State, finishing ranked in the final AP poll four times and making seven bowl games in 12 years at a school that isn't known for football dominance. He would parlay that success into an ill-fated stint at Nebraska before becoming a spring football coach with the AAF's San Antonio Commanders and UFL's New Jersey Generals.