Playing with Sinatra by Tom Dreesen
Picture this: You're a poor kid, on your knees, shining shoes in a tavern, listening to Frank Sinatra on the jukebox. Do you think you'd ever imagine that someday you'd be working on the same stage as your show business hero or playing poker at his house? Comedian Tom Dreesen didn't imagine such a thing could happen, but after he met Sinatra's attorney, Mickey Rudin, Dreesen got the job opening for Frank.
Tom recalls: "The second night I performed, Frank took me out to dinner. He said, 'I like you to do a few other dates with me, if you're interested.' Those 'few other dates' turned into 14 years on the road, playing famous venues in 40 to 50 cities a year, flying all over the world on Frank's private jet. We became close friends. I stayed at his home six times a year. I was a pallbearer at his funeral."
By the time the opportunity came along to open for Frank, Tom had already been on the road with Sammy Davis for three years, following an appearance on the Tonight Show.
Tom's early years certainly didn't foretell his rise into the entertainment stratosphere, but they did teach him to play poker. He grew up in a Southside Chicago shack with no tub or shower. His alcoholic parents reared eight children; Tom dropped out of school to help support the family. In Tom's childhood, gambling was everywhere, and he learned to play poker at age nine, continuing to play a lot while in the Navy.
Later, while working in Vegas, the comic hung around poker tables, watching pros like Amarillo Slim and Johnny Moss. Assessing Sinatra as a potential poker player, Tom says he believes the popular singer would have been a good strategist because he was a great actor. "He'd be able to keep that cool demeanor you need throughout the whole night, where your expression doesn't change if you get a 9-4 in your hand or a pair of aces."
Sinatra's impatience kept him from loving poker, but he did like the camaraderie. For 20 years, when he was home, there was a game every Sunday night at his house. Tom was, and still is, a regular at that table. "In those days it was Barbara Sinatra, Angie Dickinson, Robert Wagner, Jill St. John, Kirk Douglas, Jack Lemmon, Larry Gelbart, and their wives. We'd play for four hours, then stop and eat. Frank would be around, watching, or listening to TV, and always came over to tease me. Frank didn't think wild cards and split pots were real poker.
"Angie was the best player. She's smart and knows the game. Larry Gelbart, creator of MASH, always had a funny line. One night during a dinner break, he was anxious to get back to the game, and Larry said, 'Let's eat around to Barbara.' Jack Lemmon cracked up. Since the day he died, we don't play jacks or better anymore, only queens."
In common with his friend Frank, Tom Dreesen is involved in charitable work. Tom plays poker and golf tournament for charity as well as being a corporate motivational speaker. What he tells businessman, he says, applies equally to poker: "Believe you can win, and you will. Your brain is like a computer. Delete negative thoughts about losing. If you feel bad vibes at the table that make you uncomfortable, don't focus on them. Play the cards, not the person. If you learn how to control your thoughts, you can change your life."
Even so, Tom doesn't advise gambling with your rent money, since there is an element of chance: "It still depends on the cards. I had a pair of aces in the hole. The guy next to me opened for $500. I called and raised $500. Another guy called my $1,500 and raised a thousand. I went all-in when a third ace came up, but the guy rivered a straight flush. That's luck
Frank Sinatra is known for thousands of fabulous songs, but the one that would be the poker player's national anthem is, without a doubt, "Luck Be a Lady Tonight."
Luck was certainly a lady to Sinatra's friend Tom Dreesen.