Love Letters Written by Bob Dylan to his High School Sweetheart Are Expected to Sell Today for $800,000

A remarkable archive of 42 hand-written love letters by Bob Dylan to his high school sweetheart are up for auction today.

The music icon—known as Bob Zimmerman in those days—sent Barbara Ann Hewitt over 150 pages of notes to her home at Silver Lake Road in New Brighton, Minnesota.

Wide-ranging in scope and content, the young Dylan revealed his dreams of changing his name and selling a million records.

He offered bits of poetry, and professed his never-ending affection.

One letter describes his preparation for the Hibbing High talent show; one invites Barbara to the Buddy Holly show in Duluth. He comments on the cars and clothing becoming popular in the late 1950s and describes the records he’s listening to.

Every letter is accompanied by its original mailing envelope addressed in Dylan’s own hand, without a return address but simply signed on the flap: ‘Bob’.

The collection of 42 amorous letters from Ms. Hewitt’s estate is being auctioned off today online at RR Auction with a starting bid of $250,000. With 7 hours left in the auction, as of this writing, they’ve received no opening bid yet.

“The archive is a never-before-seen window into Bob Dylan’s formative years,” said Bobby Livingston, Executive VP at the Boston-based auction house.

While handwritten Dylan letters have sold individually in the past, the trustees of Hewitt’s estate wanted to keep this archive together to document the transformation of Bob Zimmerman into Bob Dylan.

“This archive is one of the most historic and culturally important that I’ve ever had the honor to curate and offer,” said Livingston. “They tell a story from beginning to end.”

The auction also contains an unrelated archive of 24 handwritten poems by Dylan with the subject header, Poems Without Titles, penned while at the University of Minnesota. This item currently has a bid of $76,000.

Other items up for auction from Hewitt’s estate include early drawings and several photos, including one of the earliest of signed Dylan photos known to exist, which is expected to fetch $3,000.