While serving as Commissioner of the Boston Police, O'Toole was a central figure in the controversy surrounding the fatal shooting of Victoria Snelgrove during celebrations following the Boston Red Sox victory over the New York Yankees at Yankee Stadium in Game 7 the 2004 American League Championship Series. During attempts to control the crowd that had gathered near Fenway Park, Boston police fired a "less lethal" FN 303 round, which missed its intended target and struck Snelgrove in the eye, resulting in her death approximately 12 hours later.