THE BIG T AT RG: DROPSHOT EDITION — Special Guest Darren Cahill

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.

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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