We move to Part 3 of the story….
After more than two and a half hours of scrambling for and dodging errant balls, we somehow make it to the 10th hole, where there’s a mini-buffet of sandwiches, wraps, chips, and soda. At the day’s start, Head Caddy told us to avoid eating unless we’re about to faint.
I’m not about to collapse, but I’m sweaty, kind of hungry, and, well, it’s there. Still, I’m hesitant. I’m basically the hired help. That is, until Michael digs in and encourages everyone to do the same.
“Someone’s paying for it!” he says. Taking Michael’s cue, I grab a banana and half a wrap. What are they gonna do, fire me?
As Michael enjoys some chips and Skittles, he watches the party in front of us get the big-time treatment. A mic’d-up announcer calls up each amateur and their pro. When the party’s pro, Kevin Kisner, a rookie on the tour, is announced, Michael boos him good-naturedly. Next hole, a kid asks Michael for his autograph. Michael gives him his signature, plus some one-sided conversation. Michael listens intently to what the kid has to say.

Photo courtesy Better Together
During the final six holes, The Insurance Guys start to slack. My guy even gives up on a hole or two. At about the five-hour mark, Michael gets slightly serious for the first time, reminding everyone to keep their focus. Then, on 17, Michael tees off with his hat on backward, Happy Gilmore-style. When he gets to the middle of the fairway, he just lies down for a moment. No one cares. No one’s around.
We’re one of the last parties, if not the very last, on the course. On the day’s final fairway, one of the insurance guys asks Michael somewhat rhetorically if his job is fun (“Isn’t it fun?”). Michael turns serious, explaining that it’s work, which can be “fun” at times. Money’s at stake, livelihoods, so that’s business. With that in mind and the finish line in sight, I start thinking about my tip.
Michael is a great guy, but carrying this bag and tracking these balls is work!
By the final hole (actually hole one), I’ve gained confidence, and I encourage my guy to stay sharp and finish strong. “Focus!” I command in a low voice. Maybe it helps. During the final stretch, my guy’s ball lands twenty-five yards from the green. “Two shots,” I command. My guy chips one that lands roughly six yards from the hole. As everyone looks on, my guy nails the putt. With the marathon finally over, everyone congratulates one another with handshakes. I award my guy a half-man hug, a lean, and a pat on the back. It’s awkward because it takes my guy by surprise, and he doesn’t wholeheartedly reciprocate.

Photo courtesy Caddy Time
“It was nice to meet you,” Michael tells me as he shakes my hand.
“I’ll be rooting for you,” I tell him and Putty.
I sound like a fan because I am.
I strap my guy’s clubs on the back of a cart and climb on the back of another and say farewell, thrilled that we’re done – but not a single penny richer. I wasn’t tipped for my services.
Maybe I should’ve kept my trap shut on the last hole, or perhaps it was just an oversight. The other amateurs were using friends or relatives as their caddies. Or maybe my guy thought I sucked.
Regardless, I’m beat and done with golf for good! There is one reward, though.
As The Insurance Guys sort things out, I head back to the clubhouse with the pros. Michael sits shotgun. Putty and I stand on the back.
For the short ride back, I’m one of them.
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Jon Hart is the author of Unfortunately, I was available, the undeserved sequel to Man versus Ball: One Ordinary Guy and His Extraordinary Sports Adventures.















