You can certainly say that they didn't spend their money wisely, but to call them cheap is simply inaccurate. Dean gave AJ money to spend, but it was not spent well. Remember, Dean is not a football guy, so he deferred to AJ on football matters. AJ's perceived "cheapness" was more of a personal nature, rather than financial. He could've signed Jackson for a more reasonable salary at the time of his original holdout, but AJ always put his own rep ahead of the team's best interest. If AJ was "cheap" with a player the Chargers developed, he was positively lavish with a guy who fell off the turnip truck and played a scant 5 games for the team. The Gaither signing was certainly more risky than the idea that Jackson may relapse to his bad behavior. AJ was a terrible GM in the end, because it became more about him than the team, which should always come first. His drafting of Larry English was about him trying to prove he was smarter than the "convention wisdom". He allowed his early success to go to his head.