My cousin Lenny was caddying with me on a warm July morning in 1957. Lenny's father, my Uncle Ray, my mother's brother, had died during World War II. He had been a sailor in the Navy, had gotten drunk and fallen from a pier as he was walking back to his ship. My Aunt Betty had gotten his GI insurance and received a widow's pension from the government each month. Lenny was an only child, an unheard of thing in my family where having four or five children was the norm. The GI insurance went to buy a nice little house in Groton, and Betty and Lenny lived there together, even though he was twenty six years old. Lenny had been a caddy at Shennecossett Golf Club since the summer of 1943. His one unrealized goal in life was to someday become the Caddymaster. Lenny had a slight intelligence shortfall. He looked normal, in fact he was a handsome man, and spoke well enough too, but there was a gear missing in his brain machine. He never seemed to learn anything from his experiences.
Lenny also loved to gamble. Gambling doesn't actually require that you be overly intelligent, but, for the most part, successful gambling usually requires that you be smarter than the person you are betting with.
We were just finishing up on the 14th hole, each carrying a single bag for two big gamblers. They were playing for twenty bucks a hole. My guy was a big hitter but had shown questionable putting skills so far. Lenny's guy putted well and was deadly accurate chipping around the greens, but almost never reached a green in regulation. Even on the par 3 holes. His longest yardage off the tee was around a hundred and forty yards and that was with his one wood, what would be called a driver today. The old adage that you drive for show and putt for dough wasn't always going to hold true.
"Jackie, I'll bet you a buck my guy beats your guy, total strokes from here to the clubhouse." There was one par 3, two 4's and a par 5 left, the 5 was the longest hole on the course, and the three par was 175 yards long.
"OK, Lenny, you want to make it for two bucks?"
"Sure, two bucks it is." I really liked my bet as we shook on it. The players settled up just off the 18th green. My guy had made a par on the par three, had bogied both par 4's and just missed a long eagle putt on the par 5, for a kick in birdy. Lenny's guy had bogied the par 3, made a par and a bogie on the two par 4's, and made a 7 on the par five when he sank a thirty foot putt. Each guy paid $3.00 for the loop, pretty good money for a single. When I added Lenny's two bucks to my money, I'd made $5.00 for the afternoon, not too bad.
"Who do you think will be the new Caddymaster, Jackie?" This must have been at least the third time he'd asked me that question since the round had begun. I'd told him that I had no idea the first two times he'd asked me. The head pro would announce the selection for Caddymaster in another week.
"I'm hoping it will be you, Lenny, that's what I'm hoping." I looked at Lenny as I said it, knowing it was true that that was what I was hoping, but I never really thought he'd have a chance. The Caddymaster they picked was usually a pretty sharp guy, had to be to keep all the caddies in line.
"I think they're going to give it to me this year Jackie, I really do." We'd had a new Caddymaster three times already since "Ratman" had left. Each time Lenny thought he'd be the one named, each time he was passed over for a younger, less experienced, but smarter, guy. I sensed a trend here and I was ready to exploit it to my advantage.
"Maybe you're too old Lenny, maybe they'll go with a younger guy again, like the last few times."
"This is my time, Jackie, I can feel it."
"For how much Lenny?"
"For how much, like a bet you mean?"
"Yeah, you like you for the new Caddymaster for how much?"
"You give me three to one Jackie, that's fair, and I'll bet you $50.00." Now that surprised me. I could win $50.00 or lose $150.00. Lenny and I usually bet for a buck or two, never for anything big like he was proposing.
"Let me think on it Lenny, I'll let you know in the morning. Are you sure you can afford to lose $50.00?"
"Can you stand to lose the $150.00, that's the real question you should be asking here." Damn he had a point there. If I did lose $150.00, I'd be working almost a month for nothing. I had plenty of dough saved up, but a hit like that would really hurt me. On the other hand, an extra $50.00 would come in mighty handy. I'd be 16 in November and had been saving up for a car for several years. I already had enough, but the new Pontiac's were due out in September and I'd heard rumors that they looked really sharp. I could almost afford to pay cash for a new one. Wouldn't that be sweet?
I went home that night with my head full of thoughts about Lenny's bet offer. I was at least 90% sure that Lenny wouldn't get the Caddymaster job. He was too old, he wasn't smart enough, and one of the three people that made the decision definitely didn't like Lenny. The head pro, Vic Panciera, did like Lenny, but he would go along with whoever his two assistant's picked. One assistant, Paul, I guess he liked Lenny OK, but Ted Fowler, the other assistant pro, he really didn't like Lenny. A few years ago Lenny was taking out Clara Fowler, Ted's sister. They went together for a long time, at least four years, but Lenny never asked her to marry him. It wasn't that Ted wanted Lenny for a brother in law so much. Ted just wanted to stop having to feed her, buy her clothes and generally just support her. Clara was almost 30 by now, she was a few years older than Lenny, and Lenny had been her only suitor since she left high school. She lived at home like Lenny, and Ted had to support his mother and Clara with no end to it in sight. He and Lenny had gotten into so many shouting matches over when Lenny was going to get off the dime and finally pop the question, that it had caused him and Clara to split up. It was sad in a way because Lenny was pretty lonely now and Aunt Betty had really liked Clara and would have welcomed her into her home, for the company and for Lenny's sake.
The next morning I got up early and walked over to the golf course and hung around the pro shop until I saw Ted Fowler coming out of the member's locker room. "Hi Ted, can I see you for a minute?" He looked at me trying to think of a reason why he'd want to talk to someone like me. In the end he couldn't resist his curiosity and waved me into the equipment room. This was where they took care of club cleaning and all equipment repairs. "I was wondering Ted, does my cousin Lenny have any chance of being appointed the new Caddymaster next week?"
"You're kidding, right?"
"No, I'm serious, you know that's what he's been hoping for ever since I can remember."
"Well, you tell him to hope in his left hand and shit in his right and see which one fills up the quickest."
"So, you're telling me there is absolutely no way he's the new Caddymaster then?"
"No way, absolutely not a chance." Well, I had gotten exactly what I came for, good inside information, practically straight from the horse's mouth. For some strange reason though it bothered me that my cousin was being passed over again. I left and walked over to the caddy shack and went inside. Lenny was sitting inside, playing a game of five handed Tonk. As usual, he was losing.
"Hey Lenny, making another donation to the cause?"
"What cause Jackie?"
"Cause you can't play Tonk for shit, Lenny. That cause. C'mon we need to talk about that bet." After the hand was done, Lenny slid his dime over to the winner and left the game. The other four guys in the game were giving me sour looks when their pigeon left, but I didn't care.
"Are you gonna take my bet Jackie? You'll be sorry if you do. This is my year, I just know it."
"It isn't your year Lenny, and it never will be as long as Ted is one of the guys making the selection. If I took the bet you'd just be throwing your $50.00 away. I just talked to Ted and he told me you don't have a prayer. You should just forget it Lenny. You're a great caddy and that should be enough. Why do you want the headache of being Caddymaster for anyways?"
"I just do Jackie, that's all, I just do. And I'm gonna get it this time too." What could I do? If I didn't take his money he'd just lose it to somebody else anyway. At least this way the money would stay in the family.
"All right Lenny, I've warned you. Don't be mad at me when you're paying me the fifty. I'll give you three to one for your fifty bucks that you aren't the next Caddymaster. Bet?"