Cieslewicz was born and grew up in the Milwaukee suburb of West Allis, and came to Madison as a student at the University of Wisconsin–Madison.

[3] His wife is Dianne Cieslewicz, who worked as chief of staff to state Senator Fred Risser, and they reside in the Regent Street neighborhood on Madison's near-west side.

He was also a staffer in the Wisconsin State Legislature, a lobbyist for the Nature Conservancy, and an elected member of the Dane County Board of Supervisors.

Madison's bicycle-pedestrian safety coordinator, Arthur Ross was fired in this way, in a move supported by the Wisconsin Bicycle Federation.

[citation needed] A gag rule used by Madison's Parks Department to limit employees' access to the press and to alders was compared to a practice used by Cieslewicz's own office.