This article discusses the use of Transfer of Development Rights as a means of landmark preservation in New York City. It briefly describes the history of the changes in the TDR regulations, from the prototype "adjacent lot transfer" to cases of "district wide of floating transfer". It reports on the recent (1998~1999) case of "Theater District TDR" in New York, summaries the regulations, planning impetus, and the issues raised in the public debate during the review process. It comments on the resultant litigation brought by the opposition against the City and highlights the controversial aspect of using TDR in an extended fashion. The article intends to provide the New York experience as both a positive lesson and caution to the attempt of using TDR for extended purposes in urban planning in Taiwan.