How Caddies Make the Game A Whole Lot Better

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For whatever reason, it didn’t dawn on me until about 10 minutes before we teed off at Sherwood on Monday that we’d have caddies. If it had, I would’ve been 10 times more excited than the 10 times more excited I already was than for a normal round of golf.

Caddies are such a great way to experience the game, and a luxury I’ve rarely been afforded, but one that I think would hook more people on the game if they got to experience it even once.

When you hire a caddie, you’re also hiring a tour guide, a swing coach, a greens guru, a motivational speaker, a cheerleader, a comedian, a personal assistant and more all rolled into one. In my experience, it’s a guaranteed good time, and an always memorable one, on the golf course when you have a caddie.

(And I realize that, for some people, we’re into issues of elitism here and some of people’s other pet issues with golf, but let’s suspend that for a moment, shall we?)

The first time I ever had a caddie was when I played in Jamaica, where Jamaican law requires you to play with a caddie. Our caddy’s name was Devon, and he looked like he could’ve walked right off the course from a 1970s Masters, white coveralls and all.

Anyway, I didn’t totally know what type of experience I was in for with him, but I got a pretty good idea on my first tee shot, which I hooked high into the palm trees on the mountain on the first hole.

Devon dashed off the tee box, shouting, “No worries, mon! I got it! Hit again!”

Cool! Throughout the round, Devon was basically a walking GPS, previewing holes, giving me yardages, reading my putts and at the same time, basically teaching beginner’s golf to my playing partner, all while cleaning our clubs. He balanced it all remarkably well.

Anyway, I recall it being a very relaxed round and so much fun that we went back the next day. And that’s when I hit the shot I recall most.

While playing a long par-3, I carved a 5-wood incredibly close to the hole, or so it looked to me from the tee. Doubt started to creep in though because my caddie, a man with a line for every golf shot under the sun, was silent. Finally, he approached me on the tee, took my 5-wood and handed me my putter.

“They always say the pro walks off the tee carrying his putter,” he told me, making me feel 10 feet tall walking off the box.

It turned out that the putt was much more than a tap-in, but I still saved par, and it was my hole of the trip, largely because Devon made it so.

So when a caddie named Bruce hopped into my cart on Monday, it automatically gave me a good vibe about how the round would go, regardless of the score. And, truth be told, at the beginning, it didn’t go well, but Bruce made that part memorable, too.

On the third hole, I hit a rare slice off the tee and way OB right into the backyard one of the multi-million-dollar homes. As I handed Bruce my club, he provided an interesting piece of course knowledge.

“Well, if it makes you feel any better, that’s the backyard of Britney Spears’ old house,” he said.

“Hey,” I replied, “if you’re going to lose a ball, better it be almost famous, right?”

My round turned around on the fourth hole, where Bruce’s read of a tough uphill breaking putt helped me make birdie, and a great golf day ensued from there.

Sherwood was a spectacular, borderline surreal, golf experience for me, and undoubtedly one of the five best courses I’ve ever played. I would’ve enjoyed the day regardless of how I played, but my scorecard probably would’ve looked drastically different were it not for Bruce’s guidance.

I’ve come to think of a good caddy as being like a good personal trainer: they get that 10 to 15 percent more out of you that’s hard to get out of yourself.

That certainly happened on the back nine, where it felt like Bruce had seen me swing enough to that he knew how to club me and what shots to recommend. I hit an uncommon number of good golf shots over those nine holes, but none better than on the last two.

Our next-to-last hole was a 491-yard par-5 with a green fronted by a creek. The play off the tee was to hit the left side of the fairway and let it roll right. I hit my best tee shot of the day and actually carried it past the suggested landing area.

That left me 230 out, prime yardage to get home in two with my hybrid, and Bruce was giving me the green light all the way. And I was only too willing, largely because I’d botched a similar shot on a previous par-5 off a perfect lie.

This lie, however, wasn’t so perfect. It was a bit of a side hill and especially troublesome for me because it wasn’t conducive for the stanch I needed to hit my draw. Because of this, I couldn’t get comfortable over the shot.

That’s when Bruce stepped in and redirected me.

“Take it off the right side of the bridge,” he said, causing me to focus left instead of right.

This created a dilemma. Hitting where Bruce recommended meant playing a cut, an uncertain outcome from me. Part of the allure of playing right was a bail-out area, where I could still recover for birdie if I didn’t completely pull off the approach.

Seeing I was still debating, Bruce provided the closing argument.

“Trust the read, boss. Hit the shot.”

With that, I settled in on the recommended line, and when I planted my lead leg, it felt solid. And I’d now be swinging more with the slope than against it. I was all in. And I fired.

The ball shot out like a pin-seeking dart. Tracking at the hole all the way, it easily carried the creek, hit short of the flagstick and rolled 15 feet past.

“That’s the best shot you’ve ever hit in your life, bro!” Bruce shouted, and high-fives and fist bumps ensued.

On the green, Bruce guided me to a two-putt birdie and later blamed himself for costing me eagle.

“I should’ve backed you off 20 percent on that stroke. You were a little too amped up there.”

No complaints here, Bruce. That was no gimme.

Having pocketed two birdies for the round, I was more than satisfied with my play for the day, but we still had one hole to go – a 146-yard par-3.

The hole was playing longer because the pin was tucked on the back tier. I was thinking of playing safe, but Bruce handed me my 8 and told me to go right at it. So I did.

Six feet. Another round of cheers broke out, making me suddenly feel like I had my own gallery.

Bruce greeted me at the cart by handing me my Cleveland putter and on the green he provided me with a two-word read on the putt. Straight in. And it was. Birdie!

Four birdies in a round is my record, and it wasn’t on a course nearly the caliber of Sherwood. I walked off the last hole on a golf high and ready to play 18 more. But alas we were done, and it’s probably better that way. You don’t mess with walk-off birdies. That was a first for me.

Anyway, a day like that makes you ponder the possibilities for your game. What if I had a Bruce for every round I played? Dare to dream. Friday it was back to the reality of approaches that just miss the green and birdie putts that don’t quite find the hole.

As we parted in the parking lot on Monday, I joked with Bruce that I’d like to have him in an app. that I could just open and point at the course when I needed a yardage, a read, or even maybe just a little comedic a relief.

Only I wasn’t joking. Move over, Siri. I want Bruce.