-By Penelope Karageorge

It was Frank Sinatra’s 50th birthday, and if I could not help him blow out the candles,  perhaps I could meet him. As  a reporter at Newsweek magazine, I earned a small salary but the job gave me access to the greats. I could reach out  and interview almost anyone under the Newsweek aegis. Notable exceptions were Katherine Hepburn and Frank Sinatra, who employed powerful PR firms to keep the press away..

When Harry Waters, Newsweek’s TV editor,  called  and told me he was doing a “death watch” on Sinatra, and would I like to join him, I raced out to grab a taxi. A ”death watch” is journalistic parlance for a reportorial strategy. If the story subject, in this case Sinatra, who had teams of PR people to keep the press away from him—refuses to meet the reporter, the reporter will tail the story subject—following him or her, observing what he’s wearing, who he’s with, what he drinks, eats, and any other bits of esoterica. 

When Harry called, he had been trailing Sinatra around town and come to rest at Jilly’s, a favorite Sinatra hang-out. Jilly’s was mobbed. Many of the young men boasted the Sinatra hairdo, and attempted the  Sinatra “look.” It was a room of Sinatra manqués. The singer himself sat at a long table, his back against the wall, with his date, Jill St. John, and a group of companions. A large bodyguard stood on the left of the table.

The entire room was Sinatra-obsessed. Count me among them. I finally decided that it was time to strike. I was twenty-four years old, and felt that the flirtatious rather than aggressive approach might work. I took off my coat. I was wearing my good black dress. Abandoning Harry, I walked to the large bodyguard standing next to Sinatra and told him that I was a Newsweek reporter and I had frequently tried to reach Mr. Sinatra, but had always been rebuffed. Would it be possible, just this once, to say “hello.” As I spoke with the guard—Sinatra’s table of friends, apparently hungry for diversion, took note. A  few deep voices addressed me: “Hiya, doll.” 

The bodyguard then turned to Sinatra and gave him the message. Sinatra stood up, took my hand, and continued to hold it as I told him that we had tried so many times to reach him to no avail. “I can’t imagine why,” said Sinatra, still holding my hand, and radiating—yes—sexual appeal and charisma. To which I replied—absolutely nothing! Even now I am distressed to remember that I, who prided myself on being prepared with questions, was speechless under the glow of Sinatra. Jill St John’s red hair scratched my chin as she twisted to see the woman Sinatra was talking with. His eyes were a beautiful deep blue. I thanked him again and retreated to my table where strangers in the surrounding tables said to me awed tone —“You spoke with him.” 

Afterwards, editor Harry Waters and I waited for Sinatra to leave Jilly’s and followed him in a taxi to a building on the East River. The cab driver, fearful of Sinatra—refused to go any closer to the building which stood next to a parking area. Sinatra disappeared inside to continue celebrating his 50th, and Harry and I left. Harry actually wrote a wonderful piece on Sinatra’s 50th birthday, filled with all the details we picked up along the way. 

The next day, I told my Newsweek editor that I had finally met Sinatra. “Did you get his phone number?” Bill Roeder asked, the anticlimactic aftermath to the occasion. Right now I’m playing Sinatra’s records. I never fell out of love with Sinatra’s singing, his passion, his phraseology. Nobody sang like Sinatra. He cared about the lyrics, worked on them before he ever burst into song. He was a voice—yes—and those eyes.

Leave a Reply