4. OT Jared Gaither (four-year, $24.6 million in 2012)
The 2012 offseason was a pretty bad one for the Chargers. Not only did the team overpay for a receiver who was not even an elite weapon on the Saints to begin with but the team also hitched its wagon to an unproven tackle because he did okay in a small sample size.
There is probably a good reason why this would be AJ Smith's last offseason as the general manager of the Chargers. The Bolts would go on to finish the 2012 season with a 7-9 record, leading Smith to get the boot alongside head coach Norv Turner.
At least with Meachum, there was some kind of vision there. The Gaither signing made absolutely no sense when it happened and the results of the deal should have been extremely predictable. Gaither was a backup tackle who played five games for the Bolts in 2011. It isn't like he was a homegrown developmental tackle, either, as Gaither was waived by the Kansas City Chiefs earlier that season.
Marcus McNeill would retire after the 2011 season and the Chargers thought Gaither was the guy to replace him. That netted Gaither a four-year deal that was pretty sizeable for 2012 standards only for him to play four games for the Chargers over the course of the contract. He played more the previous year when he was a backup!
Like Meachum, the Chargers released Gaither ahead of the 2013 season as a young Tom Telesco looked to start over and fix Smith's mistakes.