When a golfer gets to the putting green, it’s the caddie’s job to take the flag out of the cup, clean the player’s golf ball, and help him read the green.

To read a green is to judge how the ball is going to roll across the grass towards the hole—if it’s going to curve left, right, go uphill, downhill.

It’s on the putting greens that golfers are most confused and vulnerable, and it’s where caddies get to lord over their suddenly obedient players.

A caddie needs years to learn how to read the greens, to be able to see what needs to be seen.

For the rookie, it’s as if his vision is as fuzzy and unfocused as a newborn’s. The putting green is confoundingly flat and permanently vague.

For the veteran, it’s as if his vision is as sharp and focused as a hunter’s. The putting green is exhaustingly rugged and endlessly complicated.

With time and experience, the putting green becomes a finely contoured language, with words of grass and a grammar of shelves, swales, and slopes.

Most golfers use this language rudely and incoherently, their sentences ending with the silent dot-dot-dot ellipsis of a ball that has missed the hole, as opposed to the bobbling exclamation point of a ball that’s fallen into the cup.

Once on the putting green, the caddies squat down onto their haunches, squint their eyes, and survey the putt from multiple angles and altitudes. Those caddies who have facial hair might stroke it.

Caddies gaze at the green the way an art critic gazes at a canvas, getting up close and peering at the details, then standing back and taking in the whole. After we’ve done our survey and made our judgment, then we lean in towards the golfer and, with the hushed solemnity of the priest, the doctor, or the psychiatrist, we give the read.

“Two balls out right.” “Half-a-cup left; get it to the hole.” “Right edge; die it in the cup.”

A great caddie won’t just read the green, but will read the golfer, too. He will know how his player errs, how he gets nervous and second-guesses himself; how he doubles back on what had been the right path to take.

A caddie who could do this, who could understand his golfer better than his golfer could understand himself, was a tall, lanky, soft-spoken kid named Adam Sulloway.

The summer before he went away to college, Sulloway co-wrote a column about reading greens for the Weekly Looper. He worked on it with Surly, who turned Sulloway’s simple intuitions into long-winded theories. Surly named the column, “On the Hermeneutical Psychodynamics of Putting and Caddying.”

Sulloway was so good at reading greens that members would get upset and complain to the caddie master if he carried one golfer’s bag more often than another’s.

Some caddies dismissively said it was all just a placebo effect, that the golfers knew Sulloway’s reputation and that alone made them putt better when he was nearby.

Sulloway did admit that there was at least one golfer he had a hard time helping. This was Mr. Quentin, an investment banker in his late thirties, a guy who went to Harvard and played on the golf team there.

When Mr. Quentin hit a poor shot, he’d explain to the caddie what went wrong, how he moved his hips too fast or brought the club back too far, or how he didn’t properly visualize the shot or wasn’t fully committed to the swing.

He would do this while taking practice swings and saying how he knew exactly what the problem was, and how he was working on it with his swing coach, and how he had read in this golf magazine or that golf book about how to remedy the flaw.

He was prone to this self-critical muttering when on the putting greens, and especially when dealing with short, simple putts.

Mr. Quentin knew that he overanalyzed his swing and thought about his golf game too much. He knew that a proper pre-shot routine should clear the golfer’s mind so he could just swing the club, just let his body take over. He had read Putting Out of Your Mind, Golf Psych, as well as several golf books involving New Age spirituality and quantum mechanics.

His golf psychologist often quoted Nietzsche to him, saying: “There is more wisdom in your body than in your deepest philosophy.”

Mr. Quentin was also aware that the flock of thoughts that pecked at him while trying to play golf were the same ones that swooped in and harassed him while trying to make love to his wife, and were the same ones that loudly cawed at him while trying to write a personal investment self-help book.

He knew all this, and also knew that being aware of how self-reflexive one is just really only adds more cars to the mental traffic jam.

Nevertheless, Mr. Quentin liked to believe that, eventually, with enough mental effort, a bulldozer would rumble through the streets in his head, clearing things out and letting everything flow as he knew it could.

Sulloway had to carry Mr. Quentin’s bag during the club championship one year.

Tom Wrigley and I were waiting around on the first tee, during the first day of the tournament. We were playing with a pair of binoculars that belonged to the pro shop. We watched Sulloway and Mr. Quentin approach the green on the third hole, way off in the distance at the far corner of the golf course.

Tom had the binoculars and narrated what was happening. He said Mr. Quentin was down on his haunches, reading a long putt, while Sulloway leaned over him. They pointed at different spots on the surface of the green, gesturing with their hands and arms.

Tom reported that Mr. Quentin now stretched his head down towards the green, as he lay on his stomach in order to better read the putt. Sulloway walked around the hole, pointing at more things, variously shaking his head yes and no. The other golfer in the twosome— Mr. Quentin’s opponent—had his arms crossed and shook his head while smoking a cigarette.

Mr. Quentin went up to putt the ball.

Tom said he was now walking past the hole, as if he missed and needed to putt again. Tom then said it looked like Sulloway was asking Mr. Quentin if he needed help reading the comeback putt—what must have been a three- or four-foot little thing. Mr. Quentin shook his head, set to the ball, and stroked his putter.

Tom went, “Oh!” Mr. Quentin missed the short putt. “Oh my god!” Tom yelled. Mr. Quentin missed yet another short putt. The other golfer strode off the green, having won the hole with Quentin’s lapse.

“Way to go, Sulloway.” Tom said, putting the binoculars down.

I squinted at Sulloway and Mr. Quentin. They weren’t walking on towards the next hole. It looked like they were arguing. I told Tom to give me the binoculars. I saw Sulloway take a club out of Mr. Quentin’s golf bag, toss it on the ground, then take out a few golf balls and throw them at Mr. Quentin. Sulloway then picked up the golf bag and, grasping it in his arms like a swaddled baby, ran towards the corner of the property.

Sulloway heaved the golf bag over the tall, chain-link fence, then scurried over it and disappeared.

Mr. Quentin screamed at Sulloway. He picked up the one remaining golf club—one that looked like a mid-iron, maybe a seven-iron—and brandished it in the air.

Mr. Quentin’s opponent and his caddie, Hntsa, walked over to the scene of the dispute. They spoke for a moment. They made gestures towards the clubhouse. Mr. Quentin had his hands on his hips and shook his head, looking at where Sulloway had hopped the fence.

Mr. Quentin eventually relaxed his posture, picked up the golf balls at his feet, and, with the single golf club in hand, headed to the next hole alongside his opponent.

We found out the next day that Mr. Quentin won that match, 3-and-2, playing the rest of the round with just the seven-iron that Sulloway left for him. Hntsa said that Mr. Quentin was just walking right up to the ball and hitting it. No gratuitous practice swings, no rambling analysis afterwards. And he was especially sharp on the putting greens, using the seven-iron to make the short, easy putts that had so horribly vexed him earlier.

Sulloway brought back Mr. Quentin’s golf clubs the following morning. He walked up to the caddieshack in the same calm way as always, as if during yesterday’s round he had caddied just like any other day, as if he had read Mr. Quentin and, just as he’d read any golfer, had served him with a solution to the riddle, an answer to the question.