How I Made a Crummy Job Fun For a Moment

How I Made a Crummy Job Fun For a Moment

ChicagoNow is running a weekly special on crummy jobs. Here is my tale.

In high school my old man told me I needed to get a summer job to learn the value of a dollar, so I got a job caddying at the local country club. It was a pretty fancy country club with a Jack-Nicklaus-designed golf course and the golfing members there ranged from Cool Dudes to Complete A-holes, as you’d expect. Members had the option of taking a golf cart or a caddy, and as you can surmise, I was there for the latter.

One day I was part of a foursome that was to include two men who opted for caddies and two who had opted for carts. I knew my fellow caddy from high school, and he was an acquaintance/friend and Grade-A burnout named Eric. My favorite story about Eric was that he once told me that his mother informed him that his Orlando Magic Starter-brand windbreaker (this was in the Shaq and Penny era), “smelled like grass” and he replied with, “Oh, I know. I laid it on the grass while I was playing basketball” and she sternly answered, “You know what I mean!”.

On this particular outing it was very rainy and a lot of other golfers cancelled their outings, but not our foursome. Eric was to caddy for a guy named Dan that the caddies all loved because he was a great golfer (i.e. there weren’t any treks into the woods to find lost balls) and a nice guy who tipped $20 no matter what. I forget who I was assigned to. Since it was wet and there was a cart in the foursome, the members decided to do something a little different. Eric and I would drive the cart with all four bags in it, and essentially caddy for all four and just run each guy whatever club he asked for.

It’s also worth noting that men who opt for caddies and men who opt for carts are two distinct breeds. In general, the caddy-guys tend to be golfing purists. They are usually better golfers, sometimes they are former caddies, and they appreciate walking the course and maybe even making small talk with a caddy, whereas the cart-takers can range from being pompous A-holes to guys who just want to get in a round without talking to a pimply pipsqueak caddy.

Our outing was going pretty well and was a lot of fun for Eric and I because we actually got to drive a cart for once!! However, one of the guys who had initially signed up for a cart was a bit annoying. Most of the foursome would hit a drive then say something rational like, “Well, I’m about 250 yards out, so bring me my 4- and 5-iron and putter, and I’ll just meet you on the green.”, but this one guy kept changing his mind. He’d have us drive him over a few clubs, then he’d look at his shot for a while and as soon as we crossed the fairway and finally returned to the cart, he’d change his mind and holler for us to bring over a different club. This happened repeatedly and eventually it was just annoying to the point of condescending. Either he honestly derived pleasure from A-holeishly ordering some 15 year-olds around, or he was too much of an A-hole to even realize he was being an A-hole, and neither excuse is a good one.

By the 15th hole I’d had enough.

It’s the signature hole on this course and is tricky. This par-5 consists of a few islands and challenges the golfers to either lay-up or go all-out for the green in two strokes. Our members had decided to play a 2-on-2 match play for money and the 15 hole proved to be crunch time. The resident A-hole guy hit a nice drive, and asked for a few clubs from us before we handed them to him and drove off to service the other three. Then he called us back over for yet another change of club. Eric drove over to him and I handed him his club and feigned interest in helping him assess his shot. He had a great lie- it was teed up nicely on a bed of grass, and he opted for a club which I forget.

While he was looking at the pin, which was about 200 yards off, I looked at Eric and caught his eye. He saw me step on the guy’s ball- totally unbeknownst to everyone else- and turn his desirable lie into a ball that was halfway in the ground and halfway peaking out.

After taking a few strategic practice swings, he then looked up at us, exhaled, and said as though we gave a shit, “My partner and I really need this.”

He then swung and hit it squarely into the creek in front of the green.

DAMNIT!!!” He shouted as he looked over at us for some form of consolation. Eric and I tried not to laugh while looking at the guy and as Eric floored the cart, nearly giving me whiplash we exploded in belly-aching laughter that I still remember vividly. It was one of the most satisfying laughs of my life.

I’m not sure if I learned the value of a dollar that day, but I did learn that if you’re an anus to people, they aren’t going to care whether or not you’re happy and they will laugh at you when you fail.


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  • Orlando Magic Starter-brand windbreaker. Yes. I can clearly picture exactly who your counterpart was.

  • Unlike Harold Ramis and Bill Murray, this is all you could make of your caddying experience.

  • In reply to jack:

    How would your trolly ass know?

  • In reply to jack:

    I deleted your last comment because you referred to a family member, not because you made a decent point.

    You took exception to my "potty mouth" when it's directed at you, but not when I swear in posts which I've done at least 100 times over the years with narry a peep from you.

    You sound fragile.

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