Frank Sinatra’s Angry Letter To Chicago’s Mike Royko

Mike Royko is the quintessential Chicago columnist, mostly thanks to his efforts to piss people off. As a writer, he was one of the loudest criticizers of Chicago politics, winning a Pulitzer Prize in 1972 for commentary. Despite years as a newspaperman, his most famous publication is Boss, an unauthorized biography of Richard J. Daley. He also received and published many fan reader letters in various forms, allowing some people to share their gripes about the city and life with him, allowing others to share their displeasure of him.

One person who shared their displeasure of Royko with Royko was Frank Sinatra. Sinatra was so angry over a column Royko had written, he responded with an angry letter.

Though, to be fair, Royko started it.

In April of 1976, Frank Sinatra was in town to perform and was even granted police protection by the Chicago Police Department. Chicago, what a town!

The idea of Chicago women having to deal with “panters, breathers, grunters and other assorted lewd commentators” in Chicago without any help from police while Frank Sinatra “with his army of flunkies, has a full-time police guard” did not sit well with Royko.

So he wrote an article about it for the Chicago Daily News, which not only included the quoted remarks above, but also a few other choice insults for Ol’ Blue-Eyes to swallow.

(Credit: Chicago Daily News /

(Credit: Chicago Daily News /

“Frankly,” Royko goes on near the end of the article. “I’m surprised that Sinatra, who has such a tough reputation, would need somebody standing outside at all hours. He’s an absolute terror when it comes to punching out elderly drunks or telling off female reporters.”

My favorite part of the article shows Royko’s sharp wit in full action, when he turns the magnifying glass on himself, writing, “Well, I hate to brag, but I think that around here, I’m every bit as disliked as Sinatra. But I wouldn’t think of asking for a police guard. He’d probably dislike me, too, so what’s the advantage?”

Did Frank Sinatra shrug the column off? Did he reply with his own wit and sense of humor?

Nah, he just sent a really angry letter.

“Let me start this note by saying, I don’t know you and you don’t know me,” Sinatra wrote.

(Credit: Chicago Daily News /

(Credit: Chicago Daily News /

The piece is filled with wonderful lines. In the middle, he writes, “… who the hell gives you the right to decide how disliked I am if you know nothing about me. The only honest thing I read in your piece is the fact that you admitted you are disliked, and by the way you write I can understand it. Quite frankly, I don’t understand why people don’t spit in your eye three or four times a day.”

At the end of the letter, Sinatra offers Royko two challenges…

“Lastly, certainly not the least, if you are a gambling man: a) You prove, without a doubt, that I have ever punched an elderly drunk or elderly anybody, you can pick up $100,000. b) I will allow you to pull my “hairpiece”; if it moves, I will give you another $100,000; if it does not, I punch you in the mouth. How about it?”

Unfortunately, Royko never took Sinatra up on his offers.

The day after receiving this letter, Royko published Sinatra’s letter in the Chicago Daily News and auctioned it off to the biggest winner with the winnings going to the Salvation Army. Oddly enough, the winner happened to be Vie Carlson, mother of ex-Cheap Trick drummer Bun E. Carlos. A few years ago, Carlson and the letter made it on an episode of Antiques Roadshow, which you can see below.

You can also get a closer look at the column and letter at


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