The Frank Sinatra Rolex

My father, Johnny Ashy, was one of the original employees of Caesars Palace in Las Vegas, Nevada. After my father dealt cards and dice for several years at various casinos in Las Vegas, he was hired as Pit Boss for Blackjack when Caesars opened.

At that time in the 1960s, Frank Sinatra was one of the biggest names in entertainment. In his personal life, Mr. S (as he was known) lived hard and he gambled just as hard. As it turned out, my father was the only person at Caesars Palace who could “sort of” keep Sinatra under control. So, any time day or night that Sinatra came into Caesars to play Blackjack, my father had to come into work.

One morning at about 3:00 AM, his phone rang. When he answered it, my father was told, “your man is here, and he wants to play. Get here fast.”

When my father made it to the Blackjack pit at Caesars, Sinatra said, “it’s about time.” Surrounded by his entourage and playing by himself at his table, Sinatra started winning and kept winning. A couple of hours later he had won over $600,000. Remember, this was in the 1960s.

When Sinatra called it a night, one of his hangers-on said, “Mr. S, you did really good tonight,” to which Sinatra replied, “if the kid (which was all Sinatra ever called my father) would have been here on time, I would own this joint right now.”

Then Sinatra took off his wristwatch and tossed it to my father saying, “Here’s your tip, kid” and walked away.

The watch, which I still have to this day, is a simple, solid, Gold Rolex.