In 1976, Frank Sinatra wrote an irate letter that was signed by Vie Carlson and sent to newspaper writer Mike Royko of the Chicago Daily News.

The journalist’s negative opinion piece, which questioned the amount of police protection the artist utilized while he was in Chicago for a concert, upset the “My Way” singer to no end.

Royko said in the article that the streets were more hazardous due to the fact that Sinatra had hired some of the city’s police officers to serve as his personal bodyguard.

The irate letter included, among other things, the following passage: “Quite honestly, I don’t see why people don’t spit in your eye three or four times a day.”

In the piece, Royko also made fun of Sinatra’s hair, so the singer responded by issuing a bet challenge to the journalist at the very end of the letter.

In the letter, he said, “I will enable you to pull my ‘hairpiece.’ If it moves, I will give you another $100,000; if it does not move, I will hit you in the mouth. What do you say?”

Carlson was taken aback when appraiser Simeon Lipman said that the letter would sell at an auction for at least $15,000. “Oh whiz, I’m going to faint. After learning how much money the letter was worth, she said.

Before that, Carlson recounted the story of how she was able to get her hands on the letter in the first place. She said that she was a dedicated reader of the Chicago Daily News and that Royko was her favorite columnist since he “always favors the underdog.”

When Sinatra sent the letter to Royko, Royko published it in the newspaper and said that he would sell it to the highest bidder.

Carlson made the decision to place a bid on the letter using the cheque for $400 that she received from her family for Mother’s Day. After a couple of weeks had passed, Royko finally gave her a call to let her know that she had won the bid.