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Since 2018 Darren Winston has served as Head of Department for Books and Manuscripts, and is a Freeman's representative for the New York Connecticut, and Western Massachusetts areas. Born in Chicago and raised in Northern New Jersey, Mr. Winston moved to New York City in 1988, and began his career as a vintage bookseller in 1995. He spent the next 14 years selling at book fairs as well as privately, before opening his eponymous bookshop. Located in Sharon, Connecticut, Darren Winston, Bookseller offered vintage books, prints, and fine art, and hosted in-store events including book signings and art shows, from 2009 to 2018.

Since 2009, he has hosted the radio program "Darren Winston's Book Report" for NPR-affiliate WHDD, and he appeared in the 2014 documentary The Paper Trail, on books and paper.

Prior to joining Freeman's, Mr. Winston served as an Independent Consultant to the Fine and Rare Books Department of British luxury company Asprey, from 1999 to 2005, in their New York store. While at Asprey, he was the buyer for both the New York and Beverly Hills boutiques, and organized in-store readings with authors such as Salman Rushdie and Dominick Dunne. In 1993, he was Creative Consultant to Columbia Records, when he assisted in the repackaging of their 12-record Aerosmith back catalogue; later, Mr. Winston sold his extensive collection of their memorabilia, which he began amassing at the age of 14, directly to the band.