1. CB JC Jackson (Five-year, $82.5 million in 2022)
It isn't recency bias. JC Jackson is the worst signing of Chargers history and could ultimately be the straw that breaks the camel's back for Tom Telesco. If the Chargers fall short of winning at least one playoff game in 2023 then there is a good chance that Telesco and Brandon Staley will be canned, leaving Jackson as the GM's lasting legacy.
A lot of Chargers fans are playing hindsight general manager after this signing blew up in the team's face but the reality is that most of the fanbase was over the moon for Jackson. Sure, there were a handful of people who were concerned about paying a cornerback this much, but the overwhelming majority supported this signing.
That is what makes it so disappointing. There was never a good moment with Jackson. After an offseason full of hype, Jackson decided to have surprise surgery on his ankle (which wasn't bothering him before) right before the start of the 2022 season. That should have been the first red flag.
This delayed his Chargers debut and when he eventually did play he was awful. Jackson was terrible against the Kansas City Chiefs in Week 2, letting up the most consequential defensive touchdown of the game.
He was inactive again the following week, returned and played okay against a bad Texans and Browns team before getting benched at halftime on primetime against the Denver Broncos. Then he came back against Seattle, was getting torched, and ruptured his patellar tendon.
Hats off to Jackson for making a speedy recovery but it does not change how poorly he played to start 2023. He is the reason why the Chargers lost in Week 1 to the Dolphins. This team would be 3-1 right now if it was not for Jackson.
Jackson finished his Chargers career with just one interception and ironically enough, it still burned the team as he tried to play hero and take it out of the end zone instead of kneeing it. This gave the Chargers horrible field position, made them punt against Miami and set up a one-play touchdown drive where Tyreek Hill just ran a straight line right past Jackson.
The perfect metaphor for JC Jackson's tenure with the Chargers.