From 2005 to 2007, Chaiken served as the Director of the Maysles Film Archive and Chief Film & Video Curator of the Maysles Institute in Harlem. He assisted the Criterion Collection in their DVD releases of the Maysles Brothers’ Salesman, Gimme Shelter, Grey Gardens, and The Beales of Grey Gardens. Chaiken also helped prepare the Maysles Film Archive for donation to The Academy Film Archive in Hollywood, California, and the subsequent sale of the Maysles Films’ papers to Columbia University’s Butler Library in 2009.