Tip Your Caddie

Dillon Garcia went from running a pancake food truck to caddying at Cabot Citrus Farms — and two years later he's looping his way around the world, from Nova Scotia to New Zealand.   In this episode of the Tip Your Caddie Podcast, Doug sits down with Dillon (@dillongarcia) to talk about falling into resort caddying after a broken leg, what Cabot Citrus Farms is really like now that the old World W...

Matt Ginella has spent decades around the best courses in the world — and around the people carrying the bags at them. From Sports Illustrated to Golf Digest to Golf Channel's Round Trip, now founding Fire Pit Productions and serving as Chief Storyteller at Kemper Sports, Matt's the rare golf-media figure who treats caddies the way TYC treats them: as the people the game is actually built around....

Trey Wingo joins Dougie Buckets, confirmed the biggest guest in Tip Your Caddie history. 23 years at ESPN, two decades as the voice of NFL Sundays, now running The Wingo Network — and as it turns out, a serious caddie guy.   Doug and Trey get into the unionization fight at Pebble Beach, the loopers and courses that defined Trey's golf life (Pebble, Spyglass, Bandon, Sand Valley, St. Andrews, Carno...

What does the future of golf actually look like? And what really happens behind the scenes at Pebble Beach? This week on Tip Your Caddie, Tim Palmer from Looper Talk joins us for an honest and entertaining conversation covering Pebble Beach stories, boys golf trips, psychedelic mushrooms, bold new golf league ideas, union talk, and the future of YouTube Golf. This episode is packed with fresh pers...

What happens to the caddies when the tour they work for might not exist next year?   This week on Tip Your Caddie, we sit down with Adam, Jonathan and "Ricey" — three of the guys looping on LIV — to talk about the moment everything changed. They were at a tapas restaurant in Mexico when the news hit. Their jobs were potentially in jeopardy. Ten minutes earlier, life was normal. Ten minutes later,...

What REALLY happens out on the golf course after the members leave?   This week on Tip Your Caddie, we sit down with Mike The Caddie to talk life at Whistling Straits, massive tips, absolute horror stories out on the grass, unforgettable loops, and the best moments he's had with players over the years.   From dream rounds… to complete disasters.   This episode is pure caddie yard storytelling:   H...

Inside Bandon Dunes with caddie Mason Shamion—this one’s for the caddies and the guys who get it.   We sat down to talk about what it’s really like looping at one of the most iconic golf destinations in the world. From wild stories on the bag to dealing with all kinds of players, this episode dives into the side of golf most people never see.   If you’ve ever carried a bag, thought about caddying,...

The island green. The roars. The carnage. We pulled up a couch with the caddies who loop TPC Sawgrass and asked them everything — how many balls you really need for 17, the wildest things they've seen on that tee box, what The Players week is actually like from inside the ropes, and the loops they'll never forget.   No filters, no PR answers. Just the guys who've been watching the splashes, readin...

From pizza deliveries to fist-bumping a president.   In this episode of the Tip Your Caddie Podcast, we sit down with Pistol Pete to break down his 10-year journey in the caddie world — how he got started, how he stuck around, and how he somehow ended up caddying for celebrities, pro athletes, and even fist-bumping Donald Trump along the way.   We get into baseball stories, clubhouse chaos, and th...

The boys are officially BACK. Episode 23 of Tip Your Caddie might be the wildest one we’ve filmed in a long time.   Doug returns from an insane overseas run — playing Carnoustie, St Andrews, and then flying straight to Bandon Dunes. Lucas is fresh off a long stay back home in Kentucky with stories of his own… And then Kon shows up out of absolutely nowhere for his first appearance in YEARS.   This...

Wayne Gretzky’s longtime caddie, Jimmy, joins Tip Your Caddie to drop legendary stories from inside the ropes — from Hollywood icons to golf’s biggest names. Joe Pesci, Jack Nicholson, Clint Eastwood, Sean Connery, and plenty more make their way into Jimmy’s unbelievable tales from the fairways. Plus, he throws down a challenge to Wayne and BizNasty from TNT for an unforgettable golf match.   ⛳️...

Evan’s been looping at The Bridge for 14 years — and he’s seen it all. From celebrity loops to locker-room rumors, wild member stories, and a love life tangled up in the caddie yard. In this episode, he and his girlfriend sit down to tell the unfiltered truth about what really goes down behind the ropes.   ⛳️ Topics: Caddie life, dating on the loop, scandalous stories, biggest loops, and The Brid...

Every caddie knows this feeling — the last loop of the season. The bags are lighter, the days are shorter, and the stories start pouring out like the beers after the final round.   In Episode 20, we talk about what really happens when loop season ends — the chaos, the downtime, and the plans that somehow always involve another trip and another bet. 🎲   From end-of-season reflections to gambling p...

In Episode 19 of Tip Your Caddie, we sit down with the legend himself — Tarik. From private club loops to full-blown adventures in Asia, this one’s got it all: ✅ Wild golf stories ✅ Caddie life overseas ✅ Culture shocks ✅ Absolute madness   Whether you're in the yard or the clubhouse, you're gonna want to hear this.   🔔 Subscribe for more caddie chaos, golf deep dives, and real-ass conversati...

It’s the end of loop season, and we’re kicking off something new… Introducing the first annual Tip Your Caddie SPINZ tradition — our way of saying goodbye to summer with NFL Week 2 bets and a spin through the online casino chaos. This episode’s got football picks, slot machines, end-of-season emotions, and enough degeneracy to make a bookie blush.   🎰 Welcome to SPINZ — where the bets are bad and...

Welcome to Episode 17 of Tip Your Caddie — and trust us, this one’s different.   Cheese pulls up with hands-down the wildest caddie story we’ve ever heard. It’s got everything: chaos, characters, unbelievable moments, and a whole lot of laughs. If you’ve ever looped a day that made you question reality... this one’s for you.   We get into:   Cheese’s most outrageous bag yet   What happens when a b...

Tip Your Caddie Ep. 16 NFL season is here and we’re firing off picks like we know what we’re doing (we don’t). This week we break down our best bets, worst ideas, and the wild world of caddie life in peak season.   We talk about a week full of loops, some stock moves that might make you rich or ruin your weekend, and why caddying during football season hits different. Plus a few laughs, bad beats,...

Tip Your Caddie Ep. 15 The boys are back with a wild mix of stories from the fairways and beyond.   We kick things off with some hilarious takes on footballers trying to play golf (spoiler: not all athletes can stripe it). Then it’s straight into the chaos of August in the Hamptons — loops, heatwaves, and survival mode on the bags. Toss in a few degenerate bets, some stock picks we absolutely don’...

Tom joins Tip Your Caddie for one of our funniest episodes yet — packed with wild caddie stories, travel chaos, and unforgettable moments. From hilarious member-guest events to a day at Trump Bedminster, this one’s full of insider golf tales you won’t hear anywhere else.   We also get into the infamous blackout in the Bahamas, what really goes down when the drinks start flowing, and the kind of be...

Lucas and Jose are back... and somehow even more unhinged. In Part 2 of their Tip Your Caddie takeover, we dive deeper into the chaos of caddie life — from ridiculous loops to the weirdest things we’ve seen on a golf course.   If you liked the first one, buckle up — this one’s louder, looser, and way less filtered.   Tip Your Caddie Podcast Ep. 13 – real caddie stories, dumb jokes, and maybe a lit...

My brother Bradley and I rolled into this one in full war mode — fitting, because Shar came ready to battle us with stories. She’s our first-ever female guest on the Tip Your Caddie Podcast, and she’s got some incredible ones from looping in the Hamptons to working at Tara Iti, one of the most insane golf courses in New Zealand.   Caddie life, Hamptons loops, Tara Iti vibes, and our usual chaos —...

Caddie life gets wild. Shaun Manego joins Tip Your Caddie to tell stories from Calusa Pines, The Bridge, and beyond. We talk:   ✅ Smash or Pass: Caddie Edition ✅ Off-course stories with members ✅ Caddie season burnout & locker room laughs   If you’ve ever carried a bag, this one’s for you.   👇 Tap in & subscribe for more real caddie stories.   #golf #caddie #tipyourcaddie #golflife #sm...

Jose Liberto pulls up to the yard and does not disappoint. Argentinian roots, Hamptons loops, and a caddie attitude you can’t fake. This one’s got laughs, truth bombs, and just the right amount of chaos. If you’ve ever carried a bag, blamed your caddie, or just love the stories behind the ropes — this one’s for you.   Like, comment, and subscribe if you’ve ever hit a shot you immediately blamed on...

This week, I’m joined by my roommate, podcast co-host, and fellow bag dragger Lucas Jones. We break down the absolute grind that is caddie season in the Hamptons   We talk money, madness, who’s thriving, who’s folding, and why this summer’s shaping up to be an all-out war.  If you’ve ever wondered what the grind is like for a caddie in the summer, or what it’s like behind the scenes at one of the...

In Episode 8 of Tip Your Caddie, we’re diving into everything you need to know about this year’s PGA Championship and what’s next for caddying! 🏌️‍♂️   We kick things off by celebrating Scottie Scheffler’s incredible win at Quail Hollow 🏆 and breaking down the wildest storylines from the tournament—like Shane Lowry’s embedded ball drama and Si Woo Kim casually smoking during play. 🧐🚬   Then, we...