Bob Dylan’s Teenage Love Letters Sold for Over $650,000

Bob Dylan's Handwritten Love Letters to His High School Sweetheart Sold for Over $650,000 at Auction to a Portuguese Bookshop.

Nov 22, 2022By Angela Davic, News, Discoveries, In-depth Reporting, and Analysis
Bob Dylan
Bob Dylan and his Rolling Thunder Review play Maple Leaf Gardens in Toronto on January 10, 1974.


Bob Dylan’s teenage love letters, dedicated to Barbara Ann Hewitt, sold at an auction. The lot consists of 42 letters. Also, the letters span 150 pages hand-written by the young musician. Dylan’s love letters are now a possession of bookstore and tourist destination Livraria Lello in Porto, Portugal.


Letters to Hewitt Show the Transformation From Zimmerman to Bob Dylan

Dylan Letters
AP: Nikki Brickett/RR Auction/the Estate of Barbara Hewitt


Bob Dylan wrote the letters to Hewitt somewhere between 1957 and 1959. At that time his name was still Bob Zimmerman. Also, in 1958 Zimmerman thought of changing his name and selling a million records. Those aspirations he shared with Hewitt in his missives. They provide an insight into a period of his life, of which not much is known.


Each letter is accompanied by its original envelope and his name on it, Bob. He wrote about preparing for the local talent show, and shared short pieces of poetry. Also, he continually professed his affections for Hewitt, according to RR Auction. The lot also includes a signed Valentine’s Day card from Dylan and an unsigned handwritten note.


Bob Dylan
A sketch by Bob Dylan.


In them, as indicated in a statement released this Friday by the executive vice president of RR Auction, Bobby Livingston, you can see “the transformation of Bob Zimmerman into Bob Dylan”. Dylan is one of the most important cultural figures of all time. He is also an author of hits like “Blowin’ in the Wind” or “Mr. Tambourine Man”.

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According to the auction house, Hewitt was born in Minnesota in 1941. Due to her father’s job, she travelled across the country until landing in Dylan’s hometown of Hibbing, Minnesota in 1957. As a sophomore at Hibbing High, she sat next to Dylan in history class.


The End of Dylan’s First Love Story

Love Letters
AP: Nikki Brickett/RR Auction/the Estate of Barbara Hewitt


After Hewitt relocated to nearby New Brighton, the two began dating in December. Their exchange of letters began in January 1958 and continued at least until 1959. Dylan gave a performance at the Hibbing High talent event at that time, and Hewitt and Dylan went to see Buddy Holly perform live in Duluth.


Soon after, Hewitt discovered love with someone else, with whom she remained in a committed relationship for ten years throughout the 1960s. After that, she married a Hibbing man, and divorced him after seven years. She didn’t get married again.


Letters, signed and stamped from Dylan to Hewitt.


According to the auction company, Dylan reportedly made one phone call to Hewitt from a pay phone. This happened long after high school. He also invited her to California, but she declined. Every letter in Hewitt’s possession came with its original envelope, which Dylan frequently addressed and signed.


One-of-a-kind Dylan letters can fetch up to $30,000 at auction. The full lot’s starting bid was $250,000. It is not known if Bob Dylan tried to buy his treasure back. Ms Hewitt’s daughter found the letters after her mother died in 2020. The poems sold for almost $US 250,000 and one of the earliest known signed photographs of Dylan went for more than $US24,000.

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By Angela DavicNews, Discoveries, In-depth Reporting, and AnalysisAngela is a journalism student at the Faculty of Political Science in Belgrade and received a scholarship for continued education in Prague. She completed her internship at the daily newspaper DANAS and worked as an executive editor at Talas.