The lots include a wide range of ephemera and other more prominent artifacts that include a 1956 Western Union telegram from Monroe to Norman, an American Airlines postcard the actress sent Norman around 1955 that pictures a plane on one side and reads “Guess where I am? Love, Marilyn,” and an intimate eight-page letter to Monroe from her then husband Arthur Miller, estimated to have been written around 1960, in which he lays bare the tormented nature of their relationship at its breaking point.
“I know that, had you never met me, you would still suffer depressions [sic]. But there is something I do which is actively destroying you,” Miller writes in one passage. In another, he admits to his emotional distance and apologizes throughout for having infamously written in his personal diary, which Monroe later discovered, that he felt she was at times a burden to him. He speaks of putting aside his work in order to help her straighten her affairs and working conditions (“There is no one other person in the world whose humiliation I would have gone to such lengths to prevent….”) Miller is torn between spending time on his own development, it seems, and taking care of Monroe. “I need you healthy, Marilyn, and I need the feeling of your belief in me and my love,” he writes. “Without the last I am a goner….”
The starting bid for the memorabilia of such emotional turmoil? $50,000. (A love letter from Joe DiMaggio to Monroe sold for close to $80,000 at auction in 2014.)
Also on auction are the Christian Dior skirt suit that Monroe wore on her honeymoon with DiMaggio (starting bid at $20,000) and a letter to Norman that she signed as E.E. Cummings as a joke—though many of the letters in this auction elucidate her love and deep knowledge of poetry and literature. Some of her watercolor illustrations are also up for grabs: One with the caption “old woman looking at her hand” starts at $10,000, and another, with two captions under two figures that read “a lonely girl in a costume” and “I’d die if I could,” start at $20,000.
It appears as if the more tragic—or otherwise heart-wrenching—the ephemera, the seemingly more valuable in the context of the auction.

An undated watercolor illustration by Monroe captioned “a lonely girl in a costume” and “I’d die if I could.”
Courtesy of Heritage Auctions
A 1962 letter from Monroe’s psychiatrist, Dr. Ralph Greenson.
Courtesy of Heritage Auctions
A 1958 letter from Monroe to Norman Rosten.
Courtesy of Heritage Auctions