Henderson was out of football last season after he was released by the Raiders prior to training camp last year due a failed physical. The Raiders were ready to sign him to a $1.9 million contract but came into camp following the lockout several pounds overweight. Immediately following Henderson's released, the team gave that money to free agent offensive lineman Stephon Heyer.
After appearing in 11 games and starting 5 during the 2008 season, Henderson earned the starting left tackle spot out of camp in 2009. He would start every game that season. Through six games that season, he hadn't given up a single sack, but after that things started to erode.
This prompted the Raiders to draft Jared Veldheer in the third round of the 2010 draft. And after seven games of splitting duties, Veldheer took over as the fulltime starter. Then, with Veldheer in place, the failed physical made him an easy cut.
Henderson played right tackle at Florida State when the Raiders traded into the fifth round to draft him. The move to left tackle was mainly out of necessity as the team had no better options.
With the Chargers, he is expected to backup Jared Gaither at left tackle. But his experience as a right tackle could have him shifting back over there.