Two-handed heroes

Rupert Henry and Greg O’Shea have sailed Henry’s Lombard 34, Mistral, to victory in the Two-Handed Division of the 2022 Rolex Sydney Hobart Yacht Race.

Written by Di Pearson/RSHYR media
Photography by Salty Dingo

31 December 2022


As well as winning the Two-Handed Division, Mistral also claimed the Two-Handed ORCi win and placed third in the Corinthian IRC division.

Henry and O’Shea placed 29th overall in the Cruising Yacht Club of Australia’s (CYCA) 628 nautical mile race and were happy with their outcome.

In the Two-Handed Division, they beat their nearest rivals, Sun Fast Racing (Lee Condell and Lincoln Dews) by more than three hours on corrected time. Peter Elkington and Scott Cavanough on Pacman were third, as Elkington battled the odds to make the start line, doing last minute jobs.

Henry had a similar problem, as he left the country to take on the single-handed Route du Rhum with his Class40 boat, Eora. Unfortunately, he retired with structural failure before returning to Sydney to make final preparations for the Rolex Sydney Hobart.


The Sydney sailor said, “I was unhappy for not finishing the two races (referring to the Route du Rhum and before it, the 2021 Rolex Sydney Hobart when the same boat suffered a broken backstay).”

At the start, life was not easy, according to Henry: “It was rough – and sailing shorthanded especially. The start is chaos. The exit from the Harbour is very hard. This time, starting on third line upwind, there was no clear air.

“We were confident in ourselves, though the boat preparation was rushed, because I was away doing the Route du Rhum.

“That was on my mind, especially when we had rudder troubles east of Eddystone Point (around 185 nautical miles from the finish). I thought ‘here we go’. The port rudder and bracket parted company and both are linked. So we set up a system. We jury rigged and finished.

“At one stage we thought we could get to Tasman before the southerly, but we didn’t get there, even though we went hard. On the night of the 27th, it was blowing 25 knots, but not a cloud in the sky, it was crystal clear.”

The yachtsman felt the front pattern came in too soon. “We were praying for it to come in on the night of the 28th, but it came in the afternoon. The wind was very soft on the first night. I thought we would be further down the coast on the second morning than we were.

“We had problems with our satellite connection, so couldn’t download a lot,” he said.

“I thought about my Dad out there a lot, when I was thinking to myself ‘this is too hard’ – and he’s a lot older than me,” he said of David Henry, who also sailed two-handed on Philosopher and placed 14th in the division with co-skipper, Stephen Prince.

“I got out of bed at 5am to watch him come in.”

On the good side, Henry said, “We had a great match race with Sunrise (the UK JPK 11.80 of Thomas Kneen). That was a highlight for me. We were talking to them – we were that close.”

The most demanding part of the race, “was the afternoon and night of 27th and it was the most exhilarating downwind sailing I’ve ever done. We were sailing the boat at its limit. We saw 22 knots.

“I was amazed at how nicely the boat handled. The Lombard 34s and the Jeanneau 3300s (there were four in the race) are good in big seas downwind. They are very fast for their size.”

Mistral’s skipper believes two-handed racing is a prestigious part of the event now.

“It’s a high profile race and we put together the best campaign we all can, so yes, it’s a big deal to win.”

Will they return for the 2023 Rolex Sydney Hobart? “I think so. And with this boat. I think I’ve been changing boats too much. The Lombard 34 is just right.”

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