In 1945, Emma Bailey moved to Brattleboro, Vermont, with her husband and two children. Since their new home was an old house in need of repair, and the family was having difficulty paying bills, Bailey decided to start an auction business to supplement her husband's income.In April 1950, Bailey placed the following advertisement in the local newspaper:
The Bailey Auction Barn on Black Mountain Road is prepared to handle auction sales. Courteous and efficient handling of all consignments, large or small. We will sell anything—from a plate to an estate, signed: Emma Bailey, Brattleboro's WomanAuctioneer.
On May 12, 1950, Bailey sold her first item, a 50-year-old rocking chair, for a price of $2.50. Her Saturday auctions soon became a regular local event, and her family helped out: Bailey's husband organized the sale items, and her daughters did the record-keeping and sold concessions. Bailey sold a wide range of items, including antiques, farm tools, books, household furniture and more. In 1952, after applying to the NationalAuctioneers Association, Bailey was accepted as the first female member of the Association. She continued her auction sales for almost 20 years, before retiring "at the peak of her career" in the late 1960s. She wrote a book about her experiences, titled Sold to the Lady in the Green Hat. During her time as auctioneer, Bailey encountered some opposition based on her gender: her first auction was postponed for several weeks after a male competitor accused her of breaking a zoning law. Later, when Bailey and a rival male auctioneer both expressed interest in the same sale, the man proposed that he should get the sale because "he had a family to support", whereas Bailey already had a working husband. Bailey lost the sale. Despite her induction to the National Auctioneer's Association, Bailey was not always well supported by her peers: in 1960, when a reporter inquired about women auctioneers, the Association's response was that "although a woman had tried auctioneering in Vermont, she had found it too hard and quit". Bailey died in 1999. The Wisconsin auction house Bailey’s Honor Auction, LLC, owned by auctioneer Carol Miller, is named after Emma Bailey.
