Essex grew up in Fort Wayne, Indiana where he attended Paul Harding High School and lettered in football and basketball.

He played in the first ever U.S. Army All-American Bowl (a high school football national all-star game) on December 30, 2000.

[9] Essex's fifth career start came when he again subbed for Smith at left tackle in a playoff game on January 5, 2008, which was a narrow loss to the Jacksonville Jaguars.

[8] Essex showed promise in 2008 with strong performances in place of starting right guard Darnell Stapleton against the Chicago Bears and Minnesota Vikings.

[10] Before re-signing with Pittsburgh he fielded offers from the New York Jets and Tennessee Titans but was persuaded to return to the Steelers when he received assurances from the team that he would be given the opportunity to win a starting spot.

[11] The Steelers once again earned a trip to the Super Bowl XLV where they fell to the Green Bay Packers.

He was unable to sign a new contract due to the 2011 NFL lockout which canceled normal off-season team activities.

[12] The team eventually re-signed him toward the end of camp at Roethlisberger's urging after Essex had worked on his own to bring his weight under control.

He played a good portion of the team's third game at right tackle when the starter, rookie Marcus Gilbert, was injured.