When the Hustle Goes Wrong

An overzealous caddie and an unforgettable accident
When the Hustle Goes Wrong

On a gorgeous patch of land in a quaint American suburb, there exists a slice of golden-age golf heaven. This course is real, but, for the purposes of our story, let’s call it the Historic Golf Club. And let’s call this particular caddie Hank.

Hank was a late arrival to the caddie game. He didn’t lug a bag until college, but quickly took to the job. It irked him a little bit that there were high schoolers with more experience than him, so he doubled his efforts to make sure he rose in the ranks. This gave him a generally frenetic vibe. Hank chasing down his player’s ball was akin to Scrat from Ice Age chasing his beloved acorn.

One fateful day under the bright June sun, Hank was paired with Mr. Callahan. He was a longtime member and demanded respect, brevity and efficiency—or, in caddie vernacular, “Keep up and shut up.” Mr. Callahan was a doctor, well respected by the community. He was generally a good bag to get, as long as you didn’t take any risks and kept to yourself. They were about to embark on a round Mr. Callahan might not remember, but hectic Hank definitely wouldn’t forget. 

Through three holes, things were going swimmingly. Then came the fourth tee. Hank drew Mr. Callahan’s driver for him, unsheathed the head from the cover and perfectly propped it on the bag. He wondered if Mr. Callahan appreciated the way he set up his driver, and if that would be reflected in his tip. Mr. Callahan took the driver, made a decent pass at the ball and handed it back to Hank. Hank put the head cover back on. As he slid the grip down the bag, it went in about halfway, then hit a roadblock. Hank jabbed it in there a couple more times, trying to exert a little more force without drawing attention. Nothing. Zero movement. Nada. Was Mr. Callahan’s bag full of concrete? Hank paused his efforts as the next player in the group teed off. As soon as the ball was struck, he was back at it: Jab. Jab. Jab. It’s probably that ridiculous oversized SuperStroke grip on his putter, Hank thought to himself. The next player teed off. Back to work. It was as if Excalibur required insertion rather than extraction.

Hank inhaled slowly and gathered himself. Enough finesse. With another deep breath,  he directed all his strength into his shoulder and triceps to get it done. At that very moment, unbeknownst to dear, distracted Hank, Mr. Callahan came to get something out of his bag. With a triumphant release and overwhelming force, the driver grip finally plunged into the bottom of the bag, causing the driver head, still waggling in the air, to come crashing down directly on Mr. Callahan’s head.

Mr. Callahan staggered backward. His playing partners gasped. The caddies smirked. Hank had just smacked his player in the noggin with his own driver. Hank’s apologies were more profuse than his sweat. And it wasn’t typical caddie sweat. It was shame sweat—the worst kind. Fourteen agonizing holes were ahead of him, each an opportunity to rehash his humiliation.

Hank’s dread, the midday sun and the welt on Mr. Callahan’s head rose in unison. After collecting his meager tip and a mollifying nod from Mr. Callahan, Hank spent some time in the caddyshack reflecting on what had gone wrong. His ensuing rounds were much more subdued and careful. Well, until he yanked the entire cup out of the ground while pulling the pin a month later. But that’s a story for another day at Historic Golf Club.