ALS in pencil, signed “Lady Day,” one page, 8.5 x 11, no date but circa 1958-1959. Handwritten letter, evidently to her third and last husband, Louis McKay, described variously as a 'wannabe gangster' and 'mob enforcer' who acted as her manager. Holiday writes, in full: "Louie I am writing this on the back of my priests letter. You know Father O'Connor, Boston. I did a very silly thing I trailed you. You really must go for that I got to say Bitch don't get me wrong I am not angry just feel sort of cheap and dirty I am also sure you don’t really mean to hurt me other wise I would have made a awful stink fink. No one would have got hurt but me here. We are still friends I hope. God bless you I hope she doesn’t break your heart."
On the reverse is Father Norman O'Connor's letter to Holiday, signed "Father O'C," in full: "Billie—Excuse paper—just got a copy of your recording on Columbia with Ellis—Wonderful—thoroughly enjoy it—wanted you to know: thus this paper. How are you? Anything I can do? Let me know." In fine condition.
O’Connor’s mention of her "recording on Columbia with Ellis" refers to Lady in Satin, an album made with bandleader and arranger Ray Ellis and released in June 1958. This was the last album released in Holiday’s lifetime, and the reference allows us to date the letter to between June 1958 and her death a year later. Holiday married Louie McKay on March 28, 1957; he was abusive to her, and they were estranged when she died on July 17, 1959. In spite of his many misdeeds, Holiday remained affectionate towards him—betrayed, she expresses her complicated feelings in this letter, hoping to still be friends.
The serendipitous presence of the Rev. Norman O'Connor's autograph enhances this historic piece even further. Nicknamed the 'Jazz Priest,' he helped to popularize jazz in the 1950s, writing a weekly column for the Boston Globe and publishing freelance work in Down Beat, Metronome, and other music magazines. He served as a board member and emcee for the first Newport Jazz Festival in 1954, and hosted jazz-related shows on TV and radio for many years.
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