Value of Frank Sinatra letter shocks ‘Antiques Roadshow’ collector: ‘I’m going to faint’

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Antiques Roadshow can be entertaining, educational and on certain occasions, like Monday night, it can be down right joyous. The first collector featured on the episode was Vie Carlson, and she was hoping for a valuation of a letter written by Frank Sinatra in 1976.

Sinatra wrote the letter to Chicago journalist Mike Royko after he penned an unflattering op-ed about the famous singer in the Daily News. Among other things, Royko accused Sinatra of commandeering the Chicago police force as his own personal security detail. As a result, Royko claimed that the streets were more dangerous because criminals were allowed to run amok.

Sinatra was very displeased with Royko and wrote him a letter. In the letter he wrote, “Quite frankly, I don’t understand why people don’t spit in your eye three or four times a day.” And at the end of the letter Sinatra challenged the writer, who mocked the entertainer’s hair, to a wager.

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

The appraiser put a value of “at least” $15,000 at auction for the letter. Carlson was so overwhelmed she thought she was literally going to faint. A producer brought a chair over for the elderly woman, who graciously accepted it. She also repeatedly shouted to nearby collectors, “Did you all hear that?”

The Antiques Roadshow crew can be seen smiling as Carlson hugged and thanked everyone. Her joy was infectious and even viewers at home commented on how fun the moment was to watch.

As for what Carlson might do with the money, she said, “If I ever sell it, the money goes to the Salvation Army. So the more, the merrier.”

The original valuation of the letter took place in 2009. On Monday, Antiques Roadshow experts placed an updated value of $20,000 on the letter.

Antiques Roadshow airs Mondays at 8 p.m. on PBS.

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