In 1999, Waldman ran again for the City Commission in District E, running against retired police captain Stanley Cohen. He campaigned on his support for economic development and for an agreement between the Seminole Tribe of Florida and Coconut Creek. The "Sun-Sentinel" endorsed Waldman over Cohen, noting that he brought "experience and a wide grasp of issues to the commission." Waldman defeated Cohen by a wide margin, winning 69% of the vote to Cohen's 31%. Waldman was re-elected without opposition in 2001, 2003, and 2005.