2. Letting Adrian Phillips walk away for cheap
The Chargers have a habit of letting good players walk away for cheap, eh? This is not a case of Phillips not being an established player and then breaking out in New England. That would be more forgivable for Telesco.
Instead, this is a case of Phillips proving that he was a very talented player on the Chargers that could make an impact in a multitude of ways only for the team to let him sign with the Patriots at an abnormally low price.
Keeping Phillips may not have changed the overall trajectory of the franchise but it is a figurehead bad decision that Chargers fans should never live down.
1. Trading up to draft Kenneth Murray
It is one thing to whiff on a pick late in the first round of a draft. Not every player picked in the first round is going to pan out and expecting otherwise is silly. It is another thing to commit extra draft capital to move up in the draft to take someone who doesn't pan out.
What makes it even worse is the fact that linebacker is not even that valuable position-wise in the draft. The Detroit Lions got murdered in the media for taking the best linebacker in the draft in the first round in 2023.
The Chargers essentially took Murray with a second and a third-round pick in the 2020 NFL Draft for him to be a well-below-average linebacker that probably won't last past his rookie deal. If it wasn't for Justin Herbert, the 2020 draft class would have been the one that got Telesco fired.