Paddle Master Series

Oscar Chalupsky won his first Molokai in 1983. His last in 2012, at age 49.

In between, he won seven consecutive titles, beat double Olympic gold medalist Greg Barton at his peak, represented South Africa at the 1992 Barcelona Olympics as team captain, and built enough credibility in boat design to launch ChalupSki, his own surfski brand, in 2025.

He is the most decorated surfski paddler in history. By his own account, his edge was never fitness alone.

"I've always maintained that age is more about motivation than anything else. The stopwatch worries me far more than Father Time."

Oscar Chalupsky

Oscar now coaches paddlers all over the world. This series puts his complete teaching method into a structured video format. It is the same method he uses at in-person clinics, structured so you can work through it at your own pace.

Most paddlers train hard with poor technique

The most common mistake in surfski, which Oscar demonstrates in Lesson 2, is pulling the paddle back towards you. It feels powerful. It is not. You are pulling water backwards, not pulling the boat forwards.

The fix is not a drill. It is understanding. Once you see why the paddle must lock in the water and let your body do the work, every stroke changes.

That is the approach this series takes. Oscar does not give you a list of things to do. He explains the physics, shows you what correct movement looks like, and then gives you drills to build that movement into muscle memory: on land, on the water, and standing waist-deep so you can feel the blade without worrying about balance.

"Practice makes permanent. If you practice the wrong thing, you get worse."

Oscar Chalupsky, Lesson 23

What the 46 lessons cover

The series runs in sequence. Each section builds on the last. Work through it in order, or jump to the section where your technique breaks down.

Lessons 1–6

Foundations

Grip, blade angle, feather, the brace stroke, the forward stroke, and how to practice drills so they actually stick. Learning or re-learning these foundations is the crucial starting point.

Lessons 7–14

Land Drills

Eight isolated drills: catch and pull, top hand, locked elbow, shoulder, core, leg drive, exit, and elbow-to-knee. Each targets one piece of the stroke.

Lessons 15-23

On-water drills

The same eight drills in the boat. Oscar shows what correct technique looks like from the front, and what to feel for when you can't see yourself.

Lessons 24-33

Why it works

The physics of the forward stroke, foot strap tension, leg length, paddle feathering, remounting, adjustable paddles, and a full series summary.

Lessons 35-40

Waist-deep water drills

Standing in the water removes the balance variable. You feel the blade lock, the rotation, and the leg drive with nothing to distract you.

Lessons 41-46

Moving water

Technique under pressure. Oscar paddles behind a motorboat to train for moving water, showing how all the drill work translates to real conditions.

Filmed in 2026. His most complete teaching to date.

Oscar has run surfski clinics for decades. This series captures his teaching in its most developed form: the concepts he has refined over 40 years of racing and coaching, explained on camera with no detail skipped.

The waist-deep water drill series, in particular, is something he rarely has time to cover in a weekend clinic. On video, you can watch it, pause it, and come back to it until the movement makes sense in your body.