We examine how tactical innovations introduced by transgressive protesters during the Seattle cycle of protests contributed to the end of a long, relatively stable period of détente between police and protesters in the United States. Case studies of the demonstrations staged by the AFL-CIO and the Direct Action Network (DAN) during the 1999 WTO protests are used to reveal the divergent capacity of the negotiated management style of policing protest to control contained and transgressive protesters. We argue that the transgressive protesters' tactics, organizational structure, and decision-making processes all frustrated police attempts to control their demonstrations and contributed to DAN's ability to shut down the opening day of the WTO. We conclude by developing a framework for understanding how police responded in subsequent protests using what we describe as "strategic incapacitation" and by proposing research questions about the impact of this style of policing on subsequent protests in the U.S. and other Western democracies.