THE BIG T AT RG: DROPSHOT EDITION — Special Guest Darren Cahill
5/24/202625 min
We are LIVE from Paris. The clay is red, the stakes are historic, and The Big T is open for business. Brad Gilbert kicks off Roland Garros 2026 with the perfect guest — his close friend of over 40 years, the legendary Darren Cahill, coach of World No. 1 Jannik Sinner. Two old friends. Forty years of receipts. Everything you need to know about the most important two weeks in tennis. Both grinded the ATP Tour in the late '80s and early '90s. Both coached Andre Agassi. Both became two of the most respected minds the sport has ever produced. Darren has 7 Grand Slam titles as a coach — Brad has him beat, but only by one. With Sinner on the doorstep of a Career Grand Slam in Paris, that gap could close fast. Darren tells the story of how he got here — from running a bar to a fearless 12-year-old named Lleyton Hewitt knocking on his door. He coached the youngest World No. 1 ever, then the oldest, and now the most dominant. The throughline? He answers that here. It gets personal too. Darren shares what genuinely marvels him about Brad — including watching a card-carrying germaphobe willingly roll around in Paris clay for a BIG T photoshoot. Commitment to the brand conquers all. Then it's all Jannik Sinner, the World #1 on pace for a historic season and a self-awareness rare in any athlete at any age. Plus, the piece of advice a young Sinner received from Novak Djokovic that quietly changed the trajectory of his entire career. They revisit the 2025 the gut-punch of three championship points away at Roland Garros 2025, and what Darren learned about his player from both moments. the rivalry redefining tennis — Sinner vs. Alcaraz. Ice vs. fire. Precision vs. improvisation. Two players who like each other, already splitting Grand Slams, building something that belongs alongside Borg-McEnroe, Agassi-Sampras, Federer-Nadal. The Big 3 era is over. This is what comes next. Brad closes with one simple question — "If Jannik lifts the trophy here in Paris, what does that moment mean to you?" The answer is worth the listen alone. 🎧 Subscribe to The Big T. Leave a review. Tell a tennis fan. In this episode: 🎾 40+ years of friendship — two tennis lifers reunited in Paris 🎾 From running a bar to coaching World No. 1s — Darren's wild road 🎾 Youngest No. 1 ever, oldest No. 1 ever, most dominant No. 1 of his era 🎾 Both coached Agassi — comparing notes 30 years later 🎾 A germaphobe rolls in clay. For a photoshoot. In Paris 🎾 What makes Jannik Sinner truly generational 🎾 Advice from Novak during 2024 AO. 🎾 The 2025 RG heartbreak. What Darren learned 🎾 Sinner vs. Alcaraz — the rivalry that's redefining tennis 🎾 The Career Grand Slam. Paris 2026. History waiting to happen
Clips
Transcript preview
First 90 secondsBrad Gilbert· Host0:00
[upbeat music] Welcome to the Big T from Roland Garros. We will be with you for the next 15 days. I can't think of a better guest to start things off with, somebody I've known for over 40 years. We played against each other. We've coached against each other, worked together. Nice to have you here on the Big T, Killer Darren Cahill.
Darren Cahill· Guest0:30
Big T, a pleasure to be here. I'm a little bit nervous being interviewed by you, I must admit.
Brad Gilbert· Host0:34
You're a little bit nervous. You know, what's funny is we've worked together. Sometimes you'll coach me on that. We played together. Um, I wanna think of how did you go from playing to when you stopped with your knee injury, you were running a bar, I believe. Were you not the bar owner? How did you go from that setup to becoming a coach?
Darren Cahill· Guest0:59
Aces Bar and Bistro back in South Australia in the Central Market. So I was a part-owner in the place back there. So I went and did a bar course and, and learned to pour beers and to tap kegs and tried to find a different way to earn an income, because I, I finished my tennis when I was about 25. Had about a dozen knee operations up until I was about 25. So tried to come back, tried to work for about three years to get back onto the tour, but you can't just rely on getting back. So had to find another interest, and decided to pour beers and,