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James B. Bolen was born and raised on the south side of Chicago in the Englewood community. He was fortunate enough to attend twelve years of Catholic School before enlisting in the United States Marine Corps. After being honorably discharged from the Marine Corps, Bolen returned home to Chicago where he studied Criminal Justice at the University of Illinois at Chicago. James Bolen joined the Chicago Police Department in January 1992. During his fifteen-year career, he received four department commendations and twenty-one honorable mentions. He spent the bulk of his policing career working in the Englewood community in which he grew up.