The Complex Legend of Frank Sinatra

Frank Sinatra was a complex and flawed individual — known in his later years for alleged mob ties and angry outbursts — but he also was an extraordinary artist who spoke out against racism and bigotry at a time when such stands were controversial and risky, as Michael Winship recalls.

By Michael Winship

As concerts and other celebrations marked the 100th anniversary of Frank Sinatra’s birth on Dec. 12, I have two potent memories: one personal, the other from a time at the end of World War II when he embraced the all-American principles of equality and tolerance – religious and racial – even in the face of bigotry and bullying.

I wrote for Sinatra once. Although as I’ve become fond of saying, you didn’t so much write for Sinatra as at him.

Frank Sinatra (Dec. 12, 1915 — May 14, 1998)

Frank Sinatra (Dec. 12, 1915 — May 14, 1998)

It was 30 years ago in the fall of 1985. I was working on the script for what would turn out to be music legend Benny Goodman’s last television special, a two-hour performance and tribute for PBS. We were in touch with Benny on a daily, sometimes hourly, basis as he put together who he wanted to participate.

One day, as I sat in the office of the executive producer, Jack Sameth, Benny called and asked him, “Would you like Frank Sinatra to be on the show?” As I nodded vigorously, Jack said, of course. Sinatra was appearing at Carnegie Hall. Benny would go backstage that night and ask him.

He said yes and the next day Benny told us to contact Sinatra’s office. We called and got a confirmation that he would appear but no, we were told, he would not sing. This was absolutely non-negotiable, He’d just reminisce about Benny if we’d provide a script.

We told Benny and he said, “I’ll get him to sing,” No, we replied, he says he won’t. “Don’t worry,” Benny said. “I’ll ask him during the performance. He’ll have to sing.” Bad idea, we said. We can tell; Sinatra really, really means it.

Meanwhile, I set about finding an anecdote involving Sinatra and Goodman that I could use for the script, not so easy in those days before Google. But I found one that’s become kind of famous.

After Sinatra quit his job as boy singer with Tommy Dorsey’s big band in…

Read more