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Bob Dylan’s love letters to his high school sweetheart are up for auction

Some of the letters and photos Bob Dylan — then Bob Zimmerman — sent to Barbara Ann Hewitt, which are now being sold by Boston’s RR Auction House.courtesy of RR Auction and the Estate of Barbara Hewitt

My love, she speaks like silence — until now.

A never-before-seen batch of 42 love letters from a teenage Bob Dylan to his high school sweetheart are up for auction in Boston through Nov. 17.

There are early drawings and photo-booth shots — one appears to be among the earliest-known signed photos of his, according to Boston’s RR Auction House.

In 1957, Barbara Ann Hewitt was a sophomore at Hibbing (Minn.) High School, in history class with Bob Zimmerman, according to the auction house’s website. They began dating that December, after the Hewitts moved. The young couple exchanged letters until February 1959.


Barbara Ann Hewitt's 1959 high school yearbook photo.courtesy of RR Auction and the Estate of Barbara Hewitt

Hewitt kept the letters, totaling some 150 pages, until her death in 2020. (While Valentines can’t buy her, the lot includes a “large Valentine.”)

The contents of the letters can be seen by “qualified bidders” in Boston through Nov. 13. Selected images are online. The photos are being auctioned separately. The trustees of Hewitt’s estate wish to keep the letters together; they’ll be sold as one lot, with a starting bid of $250,000.

The Hewitt archive “is unprecedented,” RR Auction House executive vice president Bobby Livingston said. As far as he knows, there are no other known Dylan writings from 1958-59. “Nothing like this exists anywhere.”

Dylan signs the letters at least once as “Bob or Elston.” (Elston Gunnn is a famous Dylan pseudonym.)

Notably, Livingston said, “in several letters, he talks about changing his name. He’s getting rid of Bob Zimmerman.”

Bob Dylan, of course, is a construct crafted by a Minnesota kid with big dreams. You might call these letters Dylan’s prenatal stage, a sonogram of what’s taking shape.

“It’s the formative years of Bob Zimmerman transforming into Bob Dylan,” Livingston said. “The beginning of the Bob Dylan myth.”


When Livingston read the letters, he “immediately realized” the significance. Both the Bob Dylan Museum in Tulsa and “Dylan’s offices are well aware” of them he said.

The Boston auction house has earned something of a reputation for handling Dylan-obilia. The late Tony Glover’s secret Dylan trove — including handwritten lyrics and an original bootleg of “The Basement Tapes” — eventually sold through RR for $495,000. According to its website, RR has sold hundreds of other Dylan items, from a handwritten ‘61 setlist to his 1959 Hibbing High School yearbook.

Some love letters were written from study hall at Hibbing High, Livingston said. “He’s talking about the clothes he’s wearing, making fun of [classmates], talks about doowop, about changing his name to ‘Little Willie.’”

He invites Barb to a Buddy Holly concert — right before the singer’s death. On notebook paper, he draws an invented band: “‘Little’ Willie, lead singer of the Night Gales.” Little Willie looks conspicuously like Little Richard — in Zimmerman’s 1959 high school yearbook, he said he wanted “to join Little Richard.”)

A Bob Dylan drawing from the collection of letters and photos.courtesy of RR Auction and the Estate of Barbara Hewitt

Elsewhere: glimpses of his humor — on the back of a photo, he writes the names of his bandmates in “Bob Zimmerman & Satintones,” slipping in “Ritchie Valens” as lead guitarist.

Livingston theorizes that the redheaded Hewitt is both “Girl from the North Country” and the redhead in “Tangled Up in Blue.”

“If you read the letters, you’ll know they consummated their relationship on New Year’s Eve ‘57. Then she moved 200 miles away,” Livingston said, adding Bob mailed up to four letters a day. “He ached, ached, ached for her.”


Years later, Hewitt got a call from Bob in a phone booth, asking her to come to California, according to RR’s auction information; Hewitt said she couldn’t go.

Livingston said he didn’t have an exact date for the phone call, but it shows “that even after Bob was famous, he was still . . . pining for Barb.”

She eventually wed another Hibbing man; they divorced in the late 1970s after seven years of marriage and a daughter. She never remarried, according to RR’s information.

“In his myth, he hides everything,” Livingston said. But in these letters “he’s wearing his heart on his sleeve.”

For details on the auction, go to Lauren Daley can be reached at She tweets @laurendaley1.