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Webb appears to be a gentle giant whose troubled childhood might open up a window of understanding. He has been thrust into a high-profile role while searching for proper coping skills.
Kendall and Walter Cooper, who live in Texas, befriended Webb after the 6-foot-8, 335-pounder left the University of Texas amid school violations. Webb then attended Navarro (Texas) Junior College before enrolling at Division II West Texas A&M.
The Coopers became Webb's advisers and confidantes regarding all of life's lessons. They eventually became his agents through the "Word Iz Bond Agency" during the summer of 2009. Webb signed with Walter Cooper late that December, after he became eligible.
Few believed Webb would wind up as the Bears' starting right tackle in 2010. He was switched to the more critical left side in 2011 and is battling Chris Williams to retain his job this year as the Bears host the Redskins Saturday night.
Webb remains a work-in-progress and is gaining an appreciation for how far he already has come.
"Overcoming obstacles is not easy," Webb told me. "You have to find it within yourself to overcome."
Kendall Cooper said Webb fled from the bad influences around his mother's neighborhood to get his personal life together.
"She wanted him to have a clean and clear shot at success," Cooper said. "He couldn't have anymore of his 'good friends' in his life to entice him with unhealthy living. He didn't want it, nor did his mother, and this is why he lived with us during training."
Walt Cooper believes self-discipline is the key to Webb reaching his potential.
"Although J'Marcus graduated as the top recruit in high school, and was the prized recruit of the University of Texas, his off-field transgressions interrupted his entire playing career and limited his development as a football player," he said. "Those transgressions led to him being dismissed from UT and thus began a long odyssey …without much off-field guidance or development.
"He made an impulsive decision to attend a Division II school. … When J'Marcus met us, his learning had to be condensed to prepare him for one shot at the NFL over nine months. In the NFL today, one of the drivers is character. This is what drove us into action."
Bears fans and coaches are eager to see what drives Webb into action on the playing field.