Webb was born in Newport News, Virginia. He attended Warwick High School and Hampton Roads Academy under the tutelage of Coach Abe Mikell in Newport News, and played high school football for the Warwick Raiders. While working with Coach Abe Mikell, Webb developed his fundamentals and love of the game. He was a two-year starter at cornerback and wide receiver. Webb had seven career interceptions, two of which were returned for scores. He was named to first-team All-Peninsula District as a cornerback (2007), and earned honorable mention distinction as a junior.
He was also a standout track athlete at Warwick, he ran a career best time of 6.60 seconds in the 55 metres. He excelled in triple jump and long jump as well. He was named to the All-America Team in track and field.
College career
Webb decided to enroll in the College of William & Mary, where he played for the William & Mary Tribe football team from 2008 to 2012. After redshirting in 2008, he was honored as the Colonial Athletic Association (CAA) Defensive Rookie of the Year. He was also selected to the All-CAA second-team as a cornerback and to the all-league third-team as a punt returner. He was tied for second nationally with eight interceptions, including a pair of interceptions returned for touchdowns, and totaled 160 interception return yards.[1]
In 2010, he was selected to the All-CAA first-team as a cornerback and garnered second-team honors as a punt returner after finished the season with 42 tackles, 0.5 tackles for loss, an interception and six passes broken up. In 2011, he earned first-team all-conference honors at cornerback for the second consecutive season, and finished the season with 40 tackles, 3.0 tackles for a loss and two interceptions.
As a senior, he garnered first-team all-league distinction as a cornerback for the third consecutive season, he also earned second-team all-conference honors as a punt returner. He finished his career with nine postseason all-conference honors, and set a school record with 48 career starts. He started all 11 games and totaled 46 tackles, two fumble recoveries, a forced fumble, eight passes broken up and a tackle for loss. He was initiated as a member of Omega Psi Phi fraternity at William and Mary.
He made his professional regular season debut in the Dallas Cowboys’ season-opening 36–31 victory against the New York Giants. In Week 8, he collected a season-high three solo tackles and deflected a pass during a 27–23 win against the Minnesota Vikings. Webb saw an increased snap count in Weeks 9–10 after Morris Claiborne was sidelined due to a hamstring injury.[9] On December 9, 2013, Webb had a dismal performance and was benched in favor of Sterling Moore during a 45–28 loss at the Chicago Bears in a Week 13. He was surpassed by Sterling Moore on the depth chart and was demoted to the scout team for the remainder of the season.[10] Webb was inactive as a healthy scratch for the Dallas Cowboys’ 24–22 loss to the Philadelphia Eagles in a Week 17.[11] Webb finished his rookie season in 2013 with 16 combined tackles (13 solo) and one pass deflection in 15 games and zero starts.[12]
Throughout training camp, Webb competed against Sterling Moore, Tyler Patmon, Terrance Mitchell, and Dashaun Phillips to be the fourth cornerback on the depth chart.[13][14] On August 28, 2014, the Dallas Cowboys waived Webb after he was inactive for their fourth preseason game due to a hip flexor.[15]
He was activated for 11 games and played mainly on special teams. He was released by the team on September 5, 2015.[18]
Tennessee Titans
On September 9, 2015, he was signed to the Tennessee Titanspractice squad. He was promoted to the active roster on November 8, for a game against the New Orleans Saints in which he recorded his first career interception. He appeared in 9 games (2 starts), while registering 22 tackles, one interception and three passes defensed. On September 2, 2016, he was released as part of final roster cuts.[19]
New Orleans Saints
On September 14, 2016, Webb was signed by the New Orleans Saints, to provide depth at the cornerback position after Delvin Breaux suffered a broken fibula.[20] He played in 14 games with eight starts with the Saints, recording career-highs of 28 tackles and 11 passes defensed to go along with one interception.
Chicago Bears
On April 5, 2017, Webb signed a one-year contract with the Chicago Bears.[21] He was released on September 2, 2017.[22]
Cleveland Browns
On December 19, 2017, Webb signed with the Cleveland Browns.[23] He was waived on December 29, 2017.[24] He signed a reserve/future contract with the Browns on January 1, 2018.[25] He was released on March 15, 2018.[26]
New York Giants
On March 19, 2018, Webb signed a one-year contract with the New York Giants.[27]
Cincinnati Bengals
On March 14, 2019, Webb signed a three-year contract worth $10.5 million with the Cincinnati Bengals.[28] He played in 15 games with 12 starts, recording 37 tackles, seven passes defensed, and one interception.
On March 18, 2020, Webb was released by the Bengals.[29]
Arizona Cardinals
On August 21, 2020, Webb signed a one-year contract with the Arizona Cardinals.[30] He was released on August 27, 2020.[31]
San Francisco 49ers
On August 4, 2021, Webb signed a one-year contract with the San Francisco 49ers.[32] He was released on August 24, 2021.[33]
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