Chairman Holloway is a lifelong resident of Milwaukee. He is a graduate of Lincoln High School and the University of Arkansas. He received a Master of Science degree from the University of Wisconsin–Milwaukee.

Prior to serving on the County Board, Chairman Holloway was the president and CEO of Milwaukee Comprehensive Community Health, Inc., an established health care provider. He also served as the center director for the Inner City Development Project – North, in which he co-founded two health centers (George Hillard and Capitol Drive). In addition, he was a graduate research assistant at UW–Milwaukee, associate director of 4C's of Milwaukee County, Inc. and guidance counselor at Messmer High School.

Chairman Holloway co-founded the Milwaukee Minority Chamber of Commerce and the Neighborhood Advisory Committee to City Development Agency. Chairman Holloway's community and professional memberships include: Alpha Phi Alpha Fraternity; Community Development Agency; Future Milwaukee; Wisconsin Counties Association (WCA); NAACP; and National Forum of Black Public Administrators (NFBPA). He is on the Advisory Boards of the Sherman Park Association, the Metcalfe Park Association and the Roger & Leona Fitzsimonds Boys and Girls Club.

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