4. Drafting Jerry Tillery in the first round
Jerry Tillery is one of the worst draft picks that Telesco has ever made with the Chargers but to be fair, he was taken with the 28th pick in the 2019 NFL Draft. That draft was not great to begin with and it isn't like the Chargers were picking in the top 15.
But it does not change the fact that Tillery played really poorly for the Bolts while he was still with the team. It wasn't just a case of him failing to live up to expectations, either. He actively would do things in the course of the game to hurt the Chargers.
It is never bad when your first-round pick does not even make it to the end of their rookie contract, regardless of how you spin it.
3. Hiring Mike McCoy as his first head coach
It is very rare for a general manager to get a third head coach (with only two playoff wins in a decade) but that is what Telesco got when he hired Staley before the 2021 season. That is why if Staley gets fired, so will Telesco.
The first head coach that Telesco hired was easily the worst as Mike McCoy was absolutely in over his head. Granted, he does have a playoff win under his belt with the Chargers as they limped into the playoffs in 2013 and shocked the Bengals in the Wild Card Round. But that was the anomaly. McCoy was awful.
This is such a strange wagon to hitch onto as a new general manager and it is definitely a decision that Telesco probably wishes he could have back. He held back a prime Philip Rivers by hiring a bad head coach.