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White-Collar Caddy

I had just lost my job at age thirty during the dot-com bust, and suddenly the rising career arc I'd envisioned in grad school seemed more like a smothered hook. Shaken, I waited a day before breaking the news to my live-in girlfriend. It took me two more days to tell my parents. A day after that, I called Anthony.

The voice on the other end was as harried and direct as ever. "Caddie house . . . Anthony speaking," he said, no doubt expecting I was another member of the club calling to request a tee time or ask if there were caddies available.

Anthony had moved on to a club down the road from the one where we met. Back then, I was fresh out of college, trying to earn some cash and get in some free golf while I looked for a job. He was an assistant caddie master, not much older than me. We developed a mutual respect. I admired him for being fair (by caddie-master standards—he rarely played favorites in assigning loops). He could see that I wasn't just another bag toter, that I knew the game.

But we hadn't spoken in years. "Anthony, it's Paul," I said, leaving off my last name, which he probably never knew. "How've you been?"

"Hey, Paul. What's happening?" he said, as if we'd talked last week. "You looking for work?"

"Yup."

"Come on up tomorrow morning."

I rose early the next day.

I dressed in the dark, grabbed some fruit in the kitchen and, on my way out of our walk-up in lower Manhattan, slipped the sports section out of the just-delivered paper so I'd have something to read while sitting in the caddie yard waiting for a loop. It had been many years—and much career advancement—since I'd gone through this routine. Yet I still had it down.

It was a Friday in July, the peak of summer. Driving north along the Saw Mill River Parkway, the working-class homes of Yonkers yielded to leafy Westchester estates. I reached my exit and a few minutes later drove into the club.

It could have been any well-heeled country club. Members pulled up to the bag drop in late-model cars and popped their trunks. Players whacked balls on the range. A foursome teed off. Twenty or so caddies milled about, sipping coffee, bumming cigarettes and flipping through the morning papers for the lottery numbers. A few of them looked up as I approached.

"Are you a caddie or a player?" one asked me in a less-than-welcoming tone. My preppy, if scraggly, appearance—faded golf shirt, khaki shorts, running shoes—hadn't given it away.

"A caddie," I said coolly, and I took my place among them, leaning back against a wall and pulling out my sports pages for what I guessed would be a long wait.

About an hour later, Anthony walked over. He had a twosome for me, a husband and wife who were taking a cart, which meant I'd forecaddie and carry their putters. Hardly a big-money loop, but I was happy to be getting out. I found an unclaimed towel in the cart barn and wet it at one end under the water cooler for cleaning the clubs and balls. I introduced myself to the couple and jogged out to the first fairway, wringing the towel as I ran.

What I wouldn't realize until weeks later was that they were two of the nicest people at the club. Anthony knew what he was doing. Since I'd never seen the course, I had no clue where I was going, even though I assured them I'd been caddying there all summer. After each hole, I followed them to the next tee. Clearly, they realized I had lied, and didn't mind.

I caddied dozens of more times that summer. Some of the loops were a pleasure, like the foursome of contractors I had during an outing. They asked for advice on the tees ("I'd go with a two- or three-iron here and favor the left side—the fairway falls off at two hundred yards") and heeded my reads on the greens ("It looks like it goes the other way, but it's really outside right").

During the club championship, I caddied in the A-Flight final—for both players, each of whom relied on my help. The match came down to the eighteenth green. One of them had a five-foot left-to-right putt for the win. Part of me was hoping he would not ask, but sure enough he did.

"What do you think?" he said.

"Three balls out."

As he drew the putter back, I pressed my fingers together, praying that my read was correct. He stroked the ball smoothly into the hole and gave me a high five.

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