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At the time, Jack had been working "on loan" to the CIA when a lead on the notorious Abdul Rahman Yasin, architect of the 1993 World Trade Center attack, led him to Los Angeles and into the middle of one of CTU's major investigations.
Moreover, their efforts were compromised by the actions of CIA Deputy Director Tony Webster, who inadvertently learned of the mission and intended to capture Drazen alive for information on his dealings with terrorist and organized crime groups around the world.
After working together for many years, Jack and Henderson's relationship soured when Jack was poised to be a key witness in an internal affairs investigation regarding misappropriated CTU funds.
Henderson, who had conspired with his subordinate Peter Jiminez in stealing the missing money, took advantage of a deep-cover mission by Jack and Ryan Chappelle to attempt to have Bauer killed before he could implicate them.
During this mission, he first met and worked with Nina Myers and Tony Almeida, as well as analyst Jamey Farrell.
Ultimately, Jack accepted Walsh and Henderson's offer to join the agency, where he would later take a central role in preventing many more devastating terrorist attacks.