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Oscar Chalupsky won his first Molokai when he was 20 years old, back in 1983 and has won another 10 of them since then... At age 45 he's still going strong and, given the right conditions (i.e. strong downwind) he's still got to be one of the favorites to win the race.
 Oscar in the 2008 Team Epic livery
Having spent a month at the Epic Kayaks factory in China, he returned home two weeks ago to prepare for Hawaii. What does he think of his chances and what preparation has he been doing? We asked him these and other questions... read on...
Molokai is in its 32nd year - how many of them have you done?
I did my 1st in 1983 and then won 7 in a row. I've won 11; come 2nd twice; 3rd once and 4th once - last year. [Editor: So that makes 15.]
You were working in China until, what, two weeks ago? So you've had one month to train properly for the race - what's your approach? What sessions have you been doing?
In china it was too cold to train and I had too much work; I didn't do much. I have had to build up slowly and have been getting my arse kicked by my son. I have been doing 2 sessions a day: Monday Wednesday and Friday morning at 4.15am, wake up, run to the gym then do 50 minutes of core exercises, then run back. Then on Tuesday and Thursday (also in the dark) we do sprint style sessions for 50 minutes. I have to do this for my training and my son Luke's sprint training. The wind has been really bad this time of the year - there hasn't been much. I have only done one long paddle so far. Last year we couldn't find a day without wind.
Who have you been paddling with up in Durban? How are they doing?
I did one paddle with Steve Woods and Bevan Manson and I was just ahead of them, it was a small downwind so I could manage. Steve seems to be going well, Manson is building up for the Durban World Cup. [Editor: Bevan Manson is not coming to Hawaii this year.] I have done an in and out paddle with Herman and he beat me.
Has Herman trained hard for this race? Who do you rate as your major competition this year?
Herman has been doing sessions with me on the flat and we did one downwind. He is quite a long way ahead of me. Hank is also a long way ahead of me on the Thursday dice which is 9km in the flat. Herman and Hank seem to be the same speed. I think the competition will come from Herman, Hank, Dawid and maybe Tim.
How does the Kaiwi Channel rate compared to, say, our Millers Run?
The Millers run is wind waves; Molokai is huge swells that you have to go super fast to catch. Millers runs are similar to the Hawaii Kai to Outrigger Canoe Club. Also Molokai is more from the side than Millers so more skill is needed. The end of the race is huge rebound waves.
How does it compare to the kind of downwind paddling you get in Durban?
The Molokai is similar to the wind and waves we get in Durban. I would say it is nearly 100% the same.
 Oscar paddling the Epic V10 Super Elite in Hawaii - 2007
I've been told that you can divide the race into distinct stages (i.e. if the usual weather conditions prevail - ENE 20kts). The first half is straight forward; the next quarter becomes more confused and the last stage is hectic as you come past China Walls to the finish. Is that correct?
I would say the 1st part is very hard as you have to go a long way north, nearly 90degrees to the wind then you catch the wind waves that are going nearly directly behind you to catch the huge swells going to the far South. When you get close to Oahu you start getting rebounds and directly downwind wave about 5km off. Then the last part of about 3 km is paddling against a 50 km wind.
What's your advice to first time Molokai paddlers when they arrive in Hawaii to do the race?
The most important is to get into the water and recover from the Jet Lag. Then you need to do a few long paddles so that your hands get used to the warm water and hot conditions. I normally do the finish about 20 times before the race. I also suggest you try out your boat and drinking system before.
How much juice do you take for the race? What do you use?
I normally take about 2 litres and I use Cytomax. I use 3 X Cytomax gels - one for each hour.
What do you eat the night before the race - and for breakfast on the day?
I don't do carbo loading but I have a light meal with Carbos and then a few beers.
Dean Gardiner holds the official record of 3:21:26. Your time in 2000 was only seconds outside that - what was the exact time and do you feel you've got another record in you?
I think if the weather plays its part a record is on the cards. I don't know my exact time but I was a few seconds slower.
Is Molokai your favorite race? Why?
It is one of my favorite races as the weather is very predictable and the waves are huge and fast. It is one of the most beautiful places in the world. I also have a good record in Hawaii but I can say that for most of the technical races around the world.
I believe you use two GPS units - what do you use them for?
Yes I use to Garmin a 301 and 305. I use the 301 for navigation and the 305 for my speed, distance, and heart rate.
You've said that you adjust your paddle length in mid-race - what would you expect to do at Molokai? What length would you start at, and when & why would you change it?
Yes I will start at 217 then make it smaller till I am at 210 going into the wind. As I get slower I make the paddle shorter so it take the same stroke rate to go the same speed.
You've won the race 11 times - which one gave you the most satisfaction?
That is difficult as my 1st was good as Grant Kenny had won 4 and I came the 1st time and beat him. My 10th was good as it had all the big boys racing and Dean and I were going for our 10th.
Which of your Molokai's saw the most hectic weather conditions? Describe!
It's funny - in Hawaii there is nothing like Durban as you always paddle in perfect weather and the sea is blue and warm the sun shines most days. In Durban the rain and mist and wind can be so hard that you can't see anything. It is also hard to get in and out of the surf zone in Durban
I've heard that the guys at the front need to "mark" the others so that no-one gets a better line - is that what you do? Do you pick your line and stick with it? What's your approach to the tactics of the race?
I have all the info so I make my call on the day. I try and cover all the competitors and then look at the wind and waves and my GPS. I know where I am going but I still can make mistake like I did the year Clint won. [Editor: in 2006, Clint Pretorius and Oscar went head to head across the channel, but Clint took a wider line at China Walls and opened a gap on Oscar that he was unable to shut down.] I was on a good line and ahead of Clint when I went close to the wall, it took me a lot of effort to get there and when I got there the current was going the wrong way. This can happen: what normally is the best line ends up wrong.
 Molokai 2006: Clint Pretorius beats Oscar (Pic: Mark Donaldson Photography)
Who would you put on your list of great Molokai paddlers?
You would have to say Grant Kenny, Marshall Rosa, Herman and then Dean
What's the best beer in Hawaii?
There are so many but I try and drink South African beers "Millers"
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And c'mon O, putting Deano after Herman and Marshall is clearly ridiculous.
Good times ahead