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'Antiques Roadshow' guest almost faints after expert reveals the value of her Frank Sinatra letter

The letter was written to a columnist in response to a piece taking a swipe at Sinatra.
UPDATED MAR 31, 2025
Screenshots showing the guest's reaction (Cover image source: YouTube/Antiques Roadshow PBS)
Screenshots showing the guest's reaction (Cover image source: YouTube/Antiques Roadshow PBS)

Selfies with celebrities and their response on social media may be fairly common in this connected age, but in the past, getting a reply from a famous singer or actor was a big deal. A letter from the legendary Frank Sinatra comes with a lot of emotions attached to it for his fans, and such sentiments often come out on "Antiques Roadshow." The fiery and famous letter was written by the singer to a newspaper columnist at the Chicago Daily News in response to a piece that he found offensive. The letter that garnered attention then also fetched a huge appraisal from an expert, leaving the guest in possession of it shocked.

Screenshot showing the joyous moment
Screenshot showing the joyous moment (Image source: YouTube/Antiques Roadshow PBS)

In the episode, Vie Carlson shared the story of how she got the letter. “I always read the Chicago Daily News and my favorite, favorite columnist was Mike Royko," she told the show's expert, Simeon Lipman. She then explained that back in 1976, Frank Sinatra was in Chicago to perform, and at the time, the city had a problem with crime as people were getting mugged on the streets. "And Mike Royko said about the fact that Frank Sinatra had half of the Chicago police force acting as his bodyguard on this whole floor of a hotel, so he wrote a kind of cute, funny column," she explained. 

Screenshot showing the guest talking about the letters and the columns (Image source: YouTube/Antiques Roadshow PBS)
Screenshot showing the guest talking about the letters and the columns (Image source: YouTube/Antiques Roadshow PBS)

Carlson had the cut out of the column as well, placed on the board alongside the letter. She continued to explain that Sinatra didn't appreciate Royko's tone, and he fired off a letter with some harsh words in response. The columnist then wrote a few responses of his own and as the letter got famous, he decided that he would auction it off and the money would go to the Salvation Army.

"I had a $400 Mother’s Day check from my big family … and I said ‘I’ll bid $400 and a couple of weeks later the phone rang, I picked it up - ‘This is Mike Royko’ I just let out a holler," Carlson recalled about the moment she got the letter. The letter's content clearly impressed the appraiser, who pointed out a few lines and details from it for the viewers. “Quite frankly I don't understand my people don’t spit in your eye three or four times a day," Lipman read from the letter. "And then he calls Mike Royko a p***’ … he signs it Sinatra and then copyrights it, so if it's ever published, it has to be published in full," the further pointed out. 

Screenshot showing the expert talking about the letter (Image source: YouTube/Antiques Roadshow PBS)
Screenshot showing the expert talking about the letter (Image source: YouTube/Antiques Roadshow PBS)

Lipman remarked that he and his colleagues agreed that this was the best Sinatra letter they ever read. "It’s still a famous letter, people remember it today and as such I would estimate it at auction at, at least $15,000 and I wouldn’t be surprised if this letter sold for more than that," Lipman claimed. The revelation overwhelmed Carlson, who nearly lost balance. “Oh gee, I’m going to faint! I’m going to faint!” she exclaimed. Luckily, a producer of the show quickly ran to her aid and provided a seat for her.

Screenshot showing the guest's reaction (Image source: YouTube/Antiques Roadshow PBS)
Screenshot showing the guest's reaction (Image source: YouTube/Antiques Roadshow PBS)

Amidst the shock and the joy, she pointed to one of her friends off-camera saying, "He offered me $100 for it, you can’t have it for $100!" Carlson further told the producer that if she ever sold the letter, the money would go to the Salvation Army anyway. "So, the more the merrier," she said.



 

Carlson was then joined by her friend, Betty, who came over to give her a hug. "Did you hear that Betty?" Carlson exclaimed as her friend confirmed that it was all very real.

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