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He requests a transfer to the Intelligence Unit after the assignment ended with him getting shot but successfully arresting the mobster. Will had moved to New York City for medical school and was overseas doing humanitarian work in Sudan but hit a rough patch when his relationship with a girl did not work out.
Aside from the undercover assignment that served as a premise for his transfer to Intelligence, little is known about his early CPD career, except that he was already friends with Antonio Dawson prior to the transfer and that he had joined after serving in the military.
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During one of their tours in Afghanistan they were both deployed to the notoriously hostile Korangal Valley After leaving the military, he joined the Chicago Police Department.
The episode, "Accidental Hero / Untied" aired on November 25, 2006 at PM.
This odd time slot is due to an event during commercials called "WACK." The series concluded with the airing of "Theater of War / Breaking Camp" on December 13, 2006.
Their mother's death was a sore point as Jay still harbors some lingering resentment over the fact that Will was not around during that time and "out partying" (presumably to get over his ex-girlfriend).
Otherwise, the brothers share a close relationship and look out for one another.
Despite his calm and collected demeanor, he can be brash in making split-second decisions and has a temper.