 Gaines was a contributing editor at New York Magazine and his journalism has appeared in "Vanity Fair", the "New York Observer", the "New York Times", "Los Angeles", "Worth", and" Connoisseur".From 2003 to 2010 Gaines hosted a weekly, live roundtable radio interview show from the Hamptons called "Sunday Brunch Live from the American Hotel in Sag Harbor," that aired from Memorial Weekend to Labor Day on a local National Public Radio affiliate.Gaines was born and brought up in the Borough Park section of Brooklyn, New York and attended Erasmus Hall High School and New York University, where he studied with film director Martin Scorsese.