Webb was selected in the seventh round (218th pick overall) of the 2010 NFL draft by the Chicago Bears.[2][1] On May 16, 2010, Webb agreed to a four-year deal with the Bears.[3]
In 2012, Webb was listed as the starting left tackle ahead of Chris Williams.[4] In 2013, after the Bears signed Jermon Bushrod, Webb shifted to right tackle.[5] On August 30, 2013, Webb was placed on waivers by the Bears.[6]
Minnesota Vikings
On September 1, 2013, Webb was claimed off waivers by the Minnesota Vikings.[7] On December 17, 2013, he was waived by the Minnesota Vikings.[8]
On April 2, 2015, Webb signed a one-year, $745,000 free agent contract with the Oakland Raiders.[11]
Seattle Seahawks
On March 15, 2016, the Seattle Seahawks signed Webb to a two-year, $5.75 million free agent contract that includes $2.45 million guaranteed and a signing bonus of $1.20 million.[8][12] Webb was slated to be the starting right tackle but suffered a knee injury and was replaced by Garry Gilliam. He was released by the Seahawks on November 22, 2016.[13]
Webb was suspended the first four games of the 2017 season on January 21, 2017.[14]
Indianapolis Colts
On July 30, 2018, Webb signed with the Indianapolis Colts.[15] Webb started Week 1 at right tackle but sustained a hamstring injury and was placed on injured reserve on September 11, 2018.[16]
On April 5, 2019, Webb re-signed with the Colts.[17] He was released during final roster cuts on August 31, 2019.[18]
On December 12, 2020, Webb was signed to the Indianapolis Colts' practice squad.[20] He was elevated to the active roster on December 26 for the team's week 16 game against the Pittsburgh Steelers, and reverted to the practice squad after the game.[21] His practice squad contract with the team expired after the season on January 18, 2021.[22]
