This unique, intimate package of signed letters includes fascinating personal correspondence from 1984 to 1993 between entertainer Frank Sinatra and his friend, legendary New York Times crossword puzzle editor Eugene Maleska. This material comes from Maleska's widow (his second wife) and there is no doubt as to its provenance or authenticity.
The relationship between Sinatra and Maleska began some years earlier than the first letter in this package when Maleska made a clever reference to the singer in a puzzle. Sinatra, an avid crossword worker since his teens (as detailed in one of the letters) sent him a thank you note, and a friendship was born. It was a very close friendship, as these letters reveal.
Maleska, who began submitting crossword puzzles to the Times in 1943, was its crosswords editor from 1977 until his death in 1993, working from his home in Wareham, Mass. He authored and edited dozens of puzzle books and developed several new types of puzzles. He is regarded as the “father of the New York Times crosswords” and was particularly revered for his clever puns.
This package includes five typed, signed letters from Sinatra – all signed “Francis Albert,” which is how he signed correspondence to only his closest friends. Dates and content include:
Feb. 8, 1984 – A two-page letter on 7” by 10” Sinatra stationery thanking Maleska for a present he sent his wife, Barbara; thanking him for a copy of his latest book of puzzles; informing him that the newspaper in Palm Springs, Sinatra's home, was now carrying the Times puzzles; and offering belated condolences on the death of Maleska's first wife.
April 8, 1985 – A short one-page note on 6” by 8” Sinatra stationery apparently responding to a Maleska letter in which he apparently noted he'd found a Sinatra “saloon,” with Sinatra suggesting he'll find at least a half-dozen more. He also notes he's headed off on tour to Vegas, Tokyo and Hong Kong.
Jan. 4, 1988 – A one-page letter on 7” by 10” Sinatra stationery apologizing for giving Maleska “the wrong spelling of my girl's name”; thanking him for another birthday present for Barbara; noting that he is headed off to Australia; noting he and Barbara will be in New York in both March and May and want to take him out to dinner; and offering New Year's wishes.
Sept. 19, 1989 – A full one-page letter on 7” by 10” Sinatra stationery devoted to how Sinatra became hooked on crossword puzzles as a teenager, including some intimate memories and personal details of his early years in New Jersey. Sinatra also reveals how fast he could do the weekday and Sunday Times puzzles – and that he did them in pen. (See scan.)
July 28, 1993 – A short note on 6” by 8” Sinatra stationery expressing his and Barbara's sadness at news of Maleska's surgery. “We love you, and I send you a barrel of my strength!” Sinatra writes. It was Sinatra's last letter to Maleska, who died five days later of throat cancer.
This package also includes:
1 – A full editoral page from the April 5, 1985, Desert Sun newspaper in Palm Springs, Calif., containing a letter to the editor urging the newspaper to keep running Maleska's crosswords despite a reader's complaint that they were too difficult. Sinatra has marked the letter and handwritten on it, “Dot (Dorothy Uhlemann, his longtime personal secretary) – Send this to Gene. F.S.” (See scan.)
2 – Two signed notes to Maleska from Barbara Sinatra, who was also a big crossword fan. The first is dated April 1, 1988, and is on 6” by 8” stationery with her name embossed at the top. In it, she thanks Maleska for the birthday gift mentioned in Frank Sinatra's Jan. 4, 1988, letter. The second is dated September 1989 and is on a folded 6” by 8” note card with her name embossed at the fold. In it she thanks him for his new crossword book.
3 – A short note from Dorothy Uhleman dated July 28, 1993 (same date as Sinatra's last letter), informing him that the office had moved and his last letter to Sinatra had just arrived. There is also a personal message acknowledging his illness.
4 – Five long handwritten letters from Maleska to Sinatra (three originals and two photocopies). Maleska was in the habit of hand writing his letters and then having them typed up to be sent, so these are the original drafts. They contain a plethora of personal and likely unknown information about his relationship with Sinatra, far too much to detail here.
Condition on all the letters in this package is excellent, although all the Sinatra and staff letters have horizontal mailing folds. There are no envelopes for the Frank Sinatra letters, but there are for the Barbara Sinatra and Dorothy Uhlemann notes. They are in good to fair condition. The newspaper page is in very good condition, but has been folded multiple times to fit in a small envelope, which is included. We unconditionally guarantee authenticity and condition as described.
In total, this package provides an unprecedented glimpse into the relationship between a celebrity of legendary stature and an equally legendary wordsmith, both of whom in their own ways touched millions of lives daily, and clearly touched each others. And within the correspondence are several intertwined stories that make for fascinating reading. It is truly one-of-a-kind.
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