The Value of an Angry Frank Sinatra Letter Nearly Made an Antiques Collector Faint

In the 1970s, Frank Sinatra wrote an angry letter to Chicago journalist Mike Royko. Irritated by the way Royko wrote about him, the musician penned an irritated, threatening response. Decades later, a collector on Antiques Roadshow nearly passed out when she heard how much the letter was worth.

The singer had a contentious relationship with the press

Sinatra had a steaming temper and was quick to make any dissatisfaction clear, particularly when it came to the press. Relatively early in his career, Sinatra was arrested for assaulting a journalist who had written several unflattering articles about him.

“I saw red. I hit him,” Sinatra told the Baltimore Sun in 1947. “I’m sorry that it happened, but I was raised in a tough neighborhood where you had to fight at the drop of a hat.”

Another time, he paid a waiter to punch a bewildered Dominick Dunne, even though the writer wasn’t sure why Sinatra disliked him. Sinatra reportedly also leveled threats against Kitty Kelley, the author of his unauthorized biography, because of the way she covered his life.

An irritable letter from Frank Sinatra had a stunningly high value

Given his history, it’s not surprising that Sinatra would lash out at someone who wrote negatively about him. In 1976, Royko accused Sinatra of using the Chicago police for his security detail, an act that Royko believed could make the city more dangerous. Sinatra responded to the article with a letter.

“Quite frankly, I don’t understand why people don’t spit in your eye three or four times a day,” Sinatra wrote, per Yahoo.

Royko made fun of Sinatra’s hair, so the singer challenged him at the end of his letter.

“I will allow you to pull my ‘hairpiece,’” he wrote. “If it moves, I will give you another $100,000; If it does not, I punch you in the mouth. How about it?”

Vie Carlson, a collector on an episode of Antiques Roadshow, had the letter appraised. When she heard that it was worth at least $15,000, she needed to sit down. She was so stunned by the information that she genuinely feared she would faint. Antiques Roadshow later updated the value to $20,000.

“If I ever sell it, the money goes to the Salvation Army,” Carlson said. “So the more, the merrier.”

Frank Sinatra and Judy Garland’s love letter also sold for thousands of dollars

In 2016, a letter from Judy Garland to Sinatra sold for nearly $6,000. The pair had an on-and-off-again affair, and Garland wrote to thank him for a weekend together in the Hamptons. She wrote that she regretted having to leave.

“I’m deeply dissapointed to have to miss our Monday & Tuesday date,” she wrote, per RR Auction. “However its imperative that I reach Boston by Sunday. I shall be at the Ritz-Carlton either under Mrs. Vicente Minnelli or in care of Carlton Alsop. You said today that you’d been neglegent. But darling — that’s so unimportant compared to the great amount of happiness you’ve given me. I shant forget the hours weve spent together — ever!”

The intimate letter sold for $5,897.

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