Sinatra’s Letter to Mike Royko

One of my earliest writing inspirations was Mike Royko, a legendary columnist who wrote for the Chicago Tribune when I was still attending school in the Windy City. He wrote short, punchy, entertaining columns three times a week that tackled everything from politics to social issues to the woes of the Bears. I popped into the Billy Goat Tavern (of of his famous places to grab a beer) a few times, hoping to meet him, with no luck.

sinatraletterSo when I saw reports this week that an angry letter from Frank Sinatra to Royko was being auctioned off, I was intrigued.

Royko routinely pissed off a lot of people, but I wasn’t aware of a feud with Sinatra. Royko apparently wrote a column in 1975 in which he questioned why Chicago police we offering free protection for the singer, who already had bodyguards of his own. Sinatra fired off an angry letter in response (read it in full here, 10MB PDF) that called Royko a “pimp” and threatened to “punch you in the mouth” if he shouldn’t show that the singer wore a toupee. Sinatra also wonders “why people don’t spit in your eye three or four times a day.”

Stuff like this is too good to make up.

You can read the response here. It’s classic Royko:

I like you, Frank, honest. When you wore big bow ties, I wore big bow ties. When you wore big lapels and baggy pants, I wore big lapels and baggy pants. When you dated Ava Gardner, I dated Ava Grobnik. We’re a lot alike.

I don’t have a lot to say about all this other than that it’s awesome and that I still hope to someday write as well as Royko. Maybe, if I’m lucky, I’ll also piss off a few people along the way.

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