Frank Sinatra on Crossword Puzzles

When he wasn’t charming audiences with his singing and acting skills, the inimitable Frank Sinatra could often be found with his head buried in a crossword puzzle. In fact, such was his love of the trusty crossword that, when he was referenced in the New York Times crossword in the early 1980s, he wrote a thank you note to its editor, Eugene Maleska. Maleska replied, and the ensuing friendship lasted for many years with many letters exchanged.

Below: A lovely letter of thanks from Sinatra to Maleska in 1989, in which he reminisces about his introduction to crossword puzzles as a teenager.

Transcript follows.

(Source: Simmons & Simmons; Image: Frank Sinatra, via.)



September 19, 1989

Dear Gene,

Many, many, many years ago (I was about 15) I was living with my parents in Hoboken, and a school chum of mine asked me if I wanted to work for the summer months. Of course I said yes I would and he helped me get hired with a firm in Wall Street…It was Stryker & Co. My salary was $12.00 a week. I had a wonderful time delivering stock orders, picking up stock orders, etc., etc., etc. The point of this small tale is to say that my job got me into the Crossword Puzzle world.

Getting to work each morning and returning home cost me four cents each way on the ferry. I don’t remember learning a hell of a lot about stocks and bonds but – I was introduced to the world of Crossword Puzzles.

My first day to work I stood on the bow of the ferry boat to Christopher Street, where there were other men and women on their way to New York to work, doing my New York Daily News Crossword Puzzle – in pencil. Several days after I started working I noticed a man standing next to me on the ferry also doing a puzzle but in the New York Times. And what put me away was the bum was doing the puzzle in ink! Well sir, not to be outwitted, the next morning on my way to work lo and behold I whipped out a fountain pen. And boy did I ever make a mistake. I realized that without an eraser I was in a lot of trouble. After two or three weeks I wasn’t doing too badly and I fell in love with “puzzles”, and I still am, and I’m proud to say that I threw away my pencil and from that moment on I moved up to ink, and man was I ever in trouble. Obviously trying to rub out ink was impossible. The challenge delighted me. From that time on I kept timing myself to see how quickly I could complete one. Today I would say a daily puzzle is completed in 30 to 40 minutes. The Sunday puzzle is completed in 90 to 120 minutes. What a wonderful way to pass the time and also learn new answers every day.

So Gene, my boy, keep up the good work and for all puzzlers, we thank you!

(Signed, ‘Francis Albert’)

Mr. Eugene T. Maleska
c/o The Players Club
New York City