Vie with the Sinatra letter and Royko columns
At the Madison ROADSHOW in July 2009, a guest named Vie brought in a letter that famed crooner Frank Sinatra angrily penned to Chicago Daily News columnist Mike Royko in 1976. While in town to perform, Sinatra was given special police protection, which Royko objected to in his typically witty and cantankerous way. Read the full Sinatra letter
The column that started it all
Royko, who'd won the Pulitzer Prize four years earlier for his commentary, didn't shy away from big targets like Chicago Mayor Richard J. Daley, who was the subject of his best-selling book Boss.
In this column, Royko singles out Sinatra: "Every night, 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."
Sinatra: "I don't know you and you don't know me"
Sinatra's letter, which he had hand-delivered to Royko, starts off swinging.
Chicago police: "We feel that we owe him protection"
In his column, Royko interviews David Mozee, the director of news affairs for the Chicago Police Department, who defends Sinatra's round-the-clock guard, saying that the singer's notoriety and anonymous threats against him justified their decision. He also told Royko that it was common practice to give protective details to people who were doing something for the police; in Sinatra's case, he was performing at a police event.
Sinatra: "I don't understand why people don't spit in your eye"
As the letter continues, Sinatra takes aim at both Royko and his profession.
Royko: Sinatra's "an absolute terror"
Royko doesn't hold back either. He ends his column wondering why someone with a "tough reputation" like Sinatra would need police guards.
Sinatra: Royko's a "pimp"
The Chairman of the Board offers his unique interpretation of Royko's concern for Chicago's female population.
Sinatra: "I punch you in the mouth"
Sinatra closes his letter with two unusual wagers to Royko. In his next column on the subject, Royko lowers the stakes:
• "If you can prove, without a doubt, that I have ever been a pimp, I will give you $11.00. You're not the only high roller in town.
• I don't want to pull your hair. People would think we're a couple of weirdos."
The copyright guaranteed that Royko would have to print the full letter when he offered his rebuttal; however, it was Royko who got the last word. In a column titled "A charitable letter after all", Royko lays out his plans for the now infamous letter:
"So the letter is for sale — and my price is $100 or the highest bid, which will be turned over to the Salvation Army. ... I kind of like the idea of a Sinatra letter being used to help an organization that preaches against drinking spirits and running around with lewd women."
That bidder was Vie, who was visibly delighted to learn from appraiser Simeon Lipman that her $400 investment back in 1976 is now worth $15,000.
Read the full Sinatra letter
Watch the full appraisal in our ROADSHOW Archive