4. Anthony Lynn - 33-31, one playoff appearance
With the way Anthony Lynn's tenure ended in Los Angeles, I would not totally argue with any fans that rank him below Mike McCoy on this list. While things were bad with McCoy, the last two seasons of Lynn's tenure with the Bolts were two of the worst years of the century.
The Chargers gave Rivers the worst send-off possible as the team went 5-11 in his last season as a starter. Then, despite having one of the best rookie quarterbacks of all time in 2020, Lynn could not pilot his team to even be in contention.
The final record of 7-9 really hides how ugly the 2020 season was at times for the Chargers. Let's not forget about when Lynn left his rookie QB in to get manhandled in a 45-0 loss to the New England Patriots. Or when the team couldn't get a simple field goal off with plenty of time at the end of the first half against the Atlanta Falcons.
By all accounts, Lynn seems to be a great person and a fantastic player coach. He will probably have a long career being a position coach in the NFL. But he simply struggled with the most important aspects of being a head coach and it showed over and over.
That being said, Lynn has a far better season under his belt than McCoy when the 2018 Chargers went 12-4 and had many people legitimatley believing that they could make a Super Bowl run. As bad as it was at the end, that was probably the best Chargers team of the last 15 years (even if there was one other team with a better record).