After his father's death, Webb approached the CIA and was brought into the program by Neil Daniels, a supervisor in the Treadstone program, and was monitored by Dr. Albert Hirsch, who supervised the medical assessment of the Treadstone agents.
A key moment in his life came when he was ordered to murder Nykwana Wombosi, an exiled African warlord who was blackmailing the CIA into reinstating him back as head of his state or else he will expose several CIA secrets.