Andre Agassi is one of the most iconic athletes of all time — an 8-time Grand Slam champion, Olympic gold medalist, and a legend changed tennis forever.

In this episode, Andre sits down with Roscoe and Jared to explain why he’s gone all-in on pickleball — not as a gimmick, not as a cameo, but because the sport genuinely hooked him. He breaks down what tennis players don’t understand yet: pickleball isn’t just “easy” — it’s insanely nuanced, mentally exhausting, and filled with tiny variables that change everything in real time. He even explains why two hours of tennis leaves him energized… but two hours of pickleball leaves him so mentally cooked he can’t even make it to the shower.

Andre dives deep into his game and what he’s learning — what translates from tennis, what absolutely doesn’t, why the rhythm and “blood pressure” of pickleball is harder to manage, and why he’s become a right-side player focused on forehand dinks, two-handed counters, and deception. He also answers the big questions: tennis vs pickleball difficulty, what he would change about the sport (including a wild idea to widen the net posts), why pickleball struggles on TV with camera angles, how the Lifetime ball is changing singles, and why paddle “grab/spin” might matter more than pure power.

Andre tells the story of playing the US Open with Anna Leigh Waters — including the one thought he couldn’t shake: “Don’t be the first person to lose with Anna Leigh.” He shares how a back injury nearly derailed the run, how fierce Anna Leigh is as a competitor, and why pickleball has genuinely changed his life — physically, mentally, and socially — even in his mid-50s.

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1:25 — Tennis vs pickle “animosity” + Andre’s take

2:35 — The real reason he fell in love with pickleball

4:28 — Small margins + why pickle is tricky for TV

6:47 — Andre’s game: what translates from tennis + what he’s working on

9:39 — Pickleball Slam prep: when he actually got committed

11:30 — Roscoe’s Pickleball Slam story + why Andre matters to the sport

12:59 — Tennis/pickle/padel: do they grow together or cannibalize?

15:38 — Andre’s honesty: “Tennis is the Everest of racket sports”

17:07 — Crazy poker story

18:57 — US Open with Anna Leigh Waters

22:06 — How Agassi x Joola partnership happened

26:24 — Gambling in pickleball

29:39 — Andre’s dinner speech to Joola pros

31:23 — What pro would Andre play with?

33:36 — What would he change in pickleball?

40:08 — Singles evolution + the Lifetime ball changing

44:50 — What’s harder: tennis or pickleball?

47:01 — Carlos Alcaraz on a pickle court

52:53 — Pickleball Olympics path: college + scholarships

54:13 — Legacy + why he wants to help grow the game

55:38 — Has pickleball changed his life?

#pickleballers #andreagassi #pickleball #ppa #mlp