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Hilarious Stories from the Bag

From Trevino’s snake prank to Rory’s forgotten clubs, these legendary caddie stories prove that laughter is as much a part of golf as the perfect swing.

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Ah, the life of a caddie—a mix of sage advice, heavy lifting, and occasionally witnessing the absurdities of the game firsthand. While golfers may grab the spotlight, caddies are the unsung heroes who see it all: the highs, the lows, and the downright ridiculous moments that make this game so entertaining. Today, we’ll dive into some of the funniest, most legendary caddie stories in golf history. Because behind every great golfer, there’s a caddie either shaking their head or laughing under their breath.

1. “That’s in the Lumberyard” – A Classic Ben Hogan Quip

Ben Hogan, one of the most legendary players in golf history, was known for his wit as much as his precision. During one round, a fellow golfer hit a wild, wayward shot into the woods. Without missing a beat, Hogan turned to his caddie and said, “That’s in the lumberyard.” The line was so perfectly timed and so Hogan-esque that it became part of golf lore, a reminder that even the best have their moments of humor.

2. Lee Trevino’s Snake Prank

Lee Trevino, the Merry Mex, was as much a joker as he was a golf legend. One of his most famous pranks happened during a round when he pulled a rubber snake out of his bag to scare fellow players. The caddies, of course, were in on the joke, and Trevino’s laughter echoed down the fairway as his prank successfully startled the group. It’s a story that’s been told for decades, proving that golf isn’t all about serious swings and quiet greens.

3. Jack Nicklaus and the “Three I Can Handle” Line

Caddies often double as therapists, especially during stressful rounds. Jack Nicklaus’ longtime caddie, Angelo Argea, once famously said, “Jack only hit three bad shots that round, and I can handle three.” The deadpan delivery and unwavering loyalty made Angelo a fan favorite and cemented his place in golf history. It’s a testament to the caddie-golfer bond and the humor that lightens even the tensest moments.

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4. Steve Williams’ Quick Exit from Tiger’s Bag

Steve Williams, Tiger Woods’ caddie during much of his historic run, was known for his bluntness. When Tiger asked Williams to hold his putter as he switched clubs mid-round, Williams dropped it on the ground, saying, “I’m a caddie, not a valet.” While their partnership was legendary, moments like this added a touch of humor to their otherwise intense dynamic. It’s proof that even in high-stakes golf, there’s room for levity.

5. Rory McIlroy and the Forgotten Clubs

Caddies are responsible for carrying the bag, but even they can slip up. During the 2011 Hong Kong Open, Rory McIlroy’s caddie, JP Fitzgerald, accidentally left Rory’s clubs on a putting green. Rory, unaware, arrived at the first tee empty-handed, sparking a mad scramble to retrieve the bag. The incident turned into a running joke, with Rory poking fun at JP and fans applauding the lighthearted recovery.

6. Arnold Palmer’s “A Pitching Wedge and a Prayer”

The King himself, Arnold Palmer, had a knack for turning caddie wisdom into comedy gold. During one particularly tricky shot, his caddie handed him a pitching wedge and added, “And a prayer.” Palmer, with his signature grin, delivered the shot to perfection, later joking that the prayer must’ve worked. It’s one of those moments that encapsulates the humor and charm that Palmer brought to every round.

7. Phil Mickelson’s Backwards Shot, with Help from Bones

Phil Mickelson, the master of the short game, once pulled off a jaw-dropping backwards shot that left everyone stunned—including his caddie, Jim “Bones” Mackay. Before the shot, Bones quipped, “Well, this should be interesting.” The fact that Phil nailed it, with Bones shaking his head in amazement, made it an unforgettable moment in golf history and a highlight of their long partnership.

8. Seve Ballesteros and the Caddie’s English Lesson

Seve Ballesteros, one of the most charismatic players ever, once asked his caddie, Billy Foster, for the English translation of a Spanish phrase. Billy, ever the prankster, translated it incorrectly, telling Seve to say, “I love your hat” instead of “Thank you very much.” Seve unknowingly repeated the line to multiple officials and fans, causing confusion and laughter as Billy struggled to keep a straight face.

Caddies: The Heart of Golf’s Humor

Behind every incredible shot and every crushing miss, caddies are there to lighten the mood, offer advice, or pull a harmless prank. Their stories remind us that golf, for all its seriousness, thrives on moments of connection and laughter. So next time you’re out on the course, think of the caddies who’ve carried the bags—and the laughs—through history.

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On the Importance of Not Caring: A Guide to Lowering Your Score

Worry causes many issues. When you are able to just stop, a wonderful thing happens. Follow this guide from Ty Webb to learn more.

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They say golf is a game of mental fortitude, of unwavering focus, of meticulous planning. They say you must visualize the shot, commit to the swing, and execute with precision. And to them, I say, “Hogwash!” Or perhaps, “A flute with no holes, is not a flute. A donut with no hole, is a Danish.” Because, my friends, the true secret to lowering your score, to achieving that elusive state of golfing nirvana, is to simply not care. Not one whit. Not a single, solitary damn.

Think about it. When do you hit your best shots? Is it when you’re agonizing over every blade of grass, every gust of wind, every microscopic imperfection on the green? Or is it when you’re distracted, perhaps by a particularly interesting cloud formation, or the existential dilemma of whether to order a hot dog or a chili dog at the turn? It’s the latter, isn’t it? Because when you stop caring, you stop thinking. And when you stop thinking, you start playing golf.

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The golf swing, in its purest form, is an act of instinct, a fluid motion unburdened by the shackles of conscious thought. But we, in our infinite human capacity for self-sabotage, insist on overthinking it. We analyze, we dissect, we intellectualize. We turn a simple act of hitting a ball into a complex mathematical equation, a philosophical treatise on the meaning of spin and trajectory. And what is the result? A hooked drive, a chunked iron, a three-putt that would make a novice weep.

But when you don’t care, a magical transformation occurs. The tension drains from your shoulders, the grip loosens, the mind clears. You swing, not with intent, but with a blissful indifference. The ball, sensing your newfound detachment, responds in kind. It soars, it draws, it fades, it lands precisely where it was always meant to be. It’s as if the ball itself is saying, “Finally! Someone who understands me! Someone who isn’t trying to force me into submission!”

Of course, this doesn’t mean you should actively try to hit bad shots. That would be caring, in its own twisted way. No, the art of not caring is a subtle one. It’s a state of detached engagement, a Zen-like acceptance of whatever the golf course throws at you. A bad bounce? Who cares. A missed putt? Such is life. A lost ball? Perhaps it’s off on a grand adventure, a journey of self-discovery. And in that detachment, in that blissful indifference, you will find a freedom that transcends the scorecard.

So, the next time you step onto the tee, take a deep breath. Let go of your expectations, your desires, your desperate need for perfection. Embrace the chaos. Embrace the absurdity. And most importantly, embrace the profound, liberating power of not caring. For in the gentle art of indifference, you will find not only a lower score, but a deeper, more meaningful connection to the game. Or at least, a more enjoyable round.

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The Art of the Unsolicited Golf Tip: How to Annoy Your Playing Partners with Wisdom

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There’s a certain breed of golfer, a truly special individual, who believes that every swing, every putt, every moment on the course is an opportunity for unsolicited advice. They are the self-appointed gurus of the green, the unsolicited senseis of the sand trap. And while most people recoil from such an individual, I, Ty Webb, find a certain perverse charm in their relentless, often misguided, generosity. After all, what is golf if not a canvas for human folly, painted with strokes of well-intentioned, yet utterly useless, wisdom?

Consider the scenario: your playing partner, a man (or woman) of quiet desperation, is about to address the ball. Their brow is furrowed, their stance is tentative, their very soul is screaming for a moment of peace. And then, from the depths of your profound, albeit unrequested, knowledge, you unleash it: “Keep your head down!” Or, “Slow backswing!” Or, my personal favorite, delivered with a knowing wink, “Be the ball.” The effect is instantaneous. A subtle flinch. A barely perceptible sigh. The swing, already fraught with anxiety, becomes a tortured ballet of self-doubt. The ball, inevitably, finds its way into the deepest, darkest rough.

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And that, my friends, is the art. The beauty of the unsolicited golf tip lies not in its efficacy, but in its disruption. It’s a gentle reminder that even in the serene confines of the golf course, chaos lurks. It’s a subtle assertion of dominance, a playful jab at the fragile ego of your fellow golfer. It’s a way of saying, without actually saying it, “I know more than you, even if I don’t.”

Of course, there are rules to this art. Never offer a tip when someone is actually asking for one; that would be far too helpful, and thus, entirely counterproductive. Always deliver your wisdom with an air of profound nonchalance, as if the secret to a perfect swing has just casually occurred to you while contemplating the existential dread of a missed putt. And most importantly, never, ever, acknowledge the catastrophic results of your advice. A shrug, a thoughtful nod, perhaps a mumbled, “Well, that’s golf,” is all that’s required.

So, the next time you’re on the course, and you see a fellow golfer struggling, resist the urge to be genuinely helpful. Instead, embrace the art of the unsolicited golf tip. For in the gentle torment of your playing partners, you will find a profound, if slightly mischievous, joy. And who knows, perhaps in their frustration, they will, inadvertently, discover their own path to enlightenment. Or at least, a new appreciation for silence.

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Why Your Golf Balls Disappear (and It’s Not the Gophers)

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Ah, the vanishing golf ball. A phenomenon as old as the game itself, and one that has baffled, frustrated, and occasionally driven golfers to the brink of madness for centuries. Most theories involve gophers, those furry, subterranean saboteurs with an insatiable appetite for Titleists. Or perhaps a particularly aggressive squirrel, or a flock of unusually organized crows. But I, Ty Webb, have delved deeper into this mystery, and I can assure you, the truth is far more profound, and far more amusing.

Consider, if you will, the golf ball itself. A small, dimpled sphere, designed for one purpose: to be struck with great force and sent hurtling through the air. A life of constant abuse, of being smacked, sliced, and occasionally submerged in murky ponds. Is it any wonder, then, that some of these brave little spheres simply decide they’ve had enough? They yearn for freedom, for a life beyond the confines of the fairway. They dream of rolling unencumbered through fields of wildflowers, or perhaps, for the more adventurous among them, a quiet retirement in the depths of a particularly challenging water hazard.

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I’ve seen it happen, you know. A perfectly struck shot, soaring through the air, destined for glory. And then, poof. Gone. Not a trace. No splash, no rustle in the bushes, just an empty space where a golf ball once was. It’s not a gopher, my friends. It’s an escape. A liberation. That golf ball, in its infinite wisdom, has chosen a different path. It has decided that its destiny lies not in the bottom of a cup, but in the boundless expanse of the unknown.

And who are we to judge? We, who are so obsessed with control, with precision, with the rigid rules of the game. Perhaps the golf ball, in its spontaneous disappearance, is teaching us a valuable lesson about letting go. About embracing the unexpected. About the inherent futility of trying to dictate the trajectory of a small, white sphere that clearly has a mind of its own.

So, the next time your golf ball vanishes into thin air, don’t curse the gophers. Don’t blame your swing. Instead, offer a silent salute to that brave little sphere, wherever it may be. For it has achieved what many of us can only dream of: true freedom. And who knows, perhaps one day, it will return, laden with tales of its adventures, ready to impart some profound, dimpled wisdom upon us all.

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