It’s no surprise that Rat Pack crooner Frank Sinatra thought of Chicago as his kind of town. In addition to being made an honorary citizen, the famed singer, who died this week on May 14, 1998, also received 24-hour police protection, free of charge.
And not surprisingly, that’s a fact that didn’t sit well with then-Chicago Daily News columnist Mike Royko. His May 4, 1976 column, “Yes, it’s his kind of town,” so inflamed Sinatra that the singer wrote a reply and had it hand-delivered to Royko himself, prompting an odd celebrity beef that must already be in development for a future season of “Feud
The revelation that Sinatra received free protection from a tax-funded department would’ve been particularly aggravating to most Chicagoans, not just Royko. Two years earlier, the city saw its murder count for the year hit 970, a terrible record that remains intact today
“Every night,” the columnist wrote, “hundreds of scrub ladies make it from their downtown jobs to their homes, with only a heavy purse and a strong set of lungs to protect them. But Sinatra, with his army of flunkies, has a full-time police guard.”
When reached for comment, the district commander admitted that he wasn’t sure why Sinatra had a guard. The order allegedly came from downtown. Deputy Supt. Sam Nolan also refused to answer and insisted Royko talk to David Mozee, the department’s director of news affairs. Mozee claimed the performer and his people asked for protection after receiving some threatening anonymous phone calls.
Royko had no time for that excuse.
“There are women in this city who regularly hear from panters, breathers, grunters and other assorted lewd commentators,” he wrote. “Cops don’t plant themselves outside the doors of these women. They say: ‘Just hang up, lady.’
"But some drunk with 20 cents, who doesn’t like the way Ol’ Blue Eyes parts his hairpiece, can make a phone call, and the Chicago Police Department takes it seriously.”
Sinatra was “a noted person, and he’s liked and disliked,” Mozee continued. The singer planned to attend a police ceremonial event while he was performing in town, so he should get some added protection.
But ordinary citizens do nice things for police every day, Royko argued. They pay the taxes that pay police salaries for one thing.
And why would Sinatra, with the “tough reputation,” the columnist wrote, need protection at all? “He’s an absolute terror when it comes to punching out elderly drunks or telling off female reporters.”
Suffice to say, Sinatra did not care for Royko’s column — and readers got to hear about it in the next day’s paper. The singer highlighted what he felt were Royko’s most egregious claims.
“First, you would find immediately that I do not have an army of flunkies,“ Sinatra wrote, referring to Royko’s "army of flunkies” remark. To this, Royko apologized as he didn’t know if the singer actually had any flunkies — and he apologized especially to “the flunky who delivered the letter.”
“Secondly, neither myself, nor my secretary, nor my security man put in the request for police protection. It is something that’s far from necessary,“ Sinatra continued. But Royko didn’t accuse him of asking for protection. Mozee said he did.
"This point could have been easily cleared up before I wrote the column,” he said in his reply, “but every time we called your suite, your secretary got snippy and hung up.”
“And thirdly, who in the hell gives you the right to decide how disliked I am if you know nothing about me?“ Sinatra demanded, to which Royko pointed out again that Mozee said this.
Of his "tough reputation” being an allegation, the columnist relented. “After rereading your massive file of news clippings, I agree that you have never punched any ‘elderly drunks.’ Most of the drunks you punched were younger.”
To finish off his tirade, the lounge singer tells Royko that he’s no better than the “female gossip columnists” who write “crap” about his reputation, and he called the columnist a “pimp” because “you are using people to make money, just as they are.”
He also offered Royko a wager:
“(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.“
For all his criticism of Sinatra, Royko admitted that writing the previous day’s column pained him, as he was a massive fan. And receiving a hand-written letter from the great singer "was a thrill. Even if he did call me a pimp.”
“I don’t want to pull your hair,” he said of the bet. “People would think we’re a couple of weirdos.”
Royko then set new terms — if Sinatra’s hair doesn’t move, he can punch the columnist in the mouth. “I figure that fans who can’t buy tickets for your show will pay 50 cents to touch my swollen lip.”
But if it did move, Royko wouldn’t take the 100 grand. He’d just like one of the singer’s old bow ties and an original recording of “Birth of the Blues.”
“I still say it was your best song.”
You can read the full May 5, 1976 Mike Royko column, which includes Frank Sinatra’s full letter, here or check out a full collection of his columns here. Even after the Royko feud, Chicago remained Sinatra’s kind of town. Watch him sing the iconic song in 1982 here.