- refusing to permit more than 20 taxi drivers to assemble for a protest against proposed city pick-up and drop-off rules (a federal judge ruled that action unconstitutional);
- imposing strict licensing rules on sidewalk artists, and limiting severely the number of such artists who could display their work near the Metropolitan Museum of Art (a policy struck down by the federal court of appeals as a violation of artists' rights);
- imposing a $45 a day permit fee on street musicians, which a federal district judge held excessive and far beyond any actual city costs;
- barring city employees from talking to reporters without specific approval - a policy which the federal appeals court found in violation of public workers' free speech rights;
- directing the transit authority not to display on city buses ads bought by New York Magazine which contained a gentle if critical caricature of the mayor's quest for publicity (an order held by federal district and appeals courts to be in violation of the First Amendment);
- barring a Lutheran church group from demonstrating and conducting an AIDS education program in a city park (a ban which a New York state appellate court held in clear violation of free speech);
- using city licensing power to terminate the franchises of certain newsstands and raising the fees for other newsstands on the basis of the content of publications they carry (a policy that was partly invalidated by a federal judge, ruling that newsstand operators do have First Amendment rights and that the city's claimed too much discretion in the standards it had set);
- refusing a permit for a parade or march designed to protest police brutality (a federal judge, ruling that the permit denial violated free speech, implied that the action had reflected the city's objection to the subject matter);
- suspending and later firing a city police officer who appeared in blackface, while off duty and in civilian dress, taking part in an undeniably racist skit on a Labor day parade float (a suit on behalf of the police officer, and two fire fighters suspended for the same acts, is still pending in federal court);
- barring most public events - starting with a rally to commemorate World AIDS Day - from being held on then steps of City Hall, which had long been a forum for such expressive gatherings (a policy promptly struck down by a federal district judge on free speech grounds);