Warrnambool racing carnival: former jumps jockey Kevin Wynne reflects on his career

Two-time Grand Annual winning jockey Kevin Wynne says the Warrnambool racing carnival is the greatest, and anyone who doesn’t enjoy themselves is “hard to please”.

Kevin Wynne in his job as clerk of the course at Mornington.

Kevin Wynne knows a thing or two about staying power.

He was a jumps jockey for almost 50 years, winning Grand Nationals, Great Easterns and his favourite race, the Grand Annual Steeplechase at Warrnambool (twice).

When he stopped race riding in the early 2000s, he began another career — as a clerk of the course at Victorian race meetings.

At 77, he’s a legend of racing.

Q: How long did you ride for?

Wynne: I started in 1956 and went through to 2000.

Q: Why did you give it away?

Wynne: For the rides I was getting at the finish - jumpers that no one else would ride and by the time I laid the insurance and everything I was losing. I’d rather give the money to the kids. So I gave it away.

Kevin Wynne with trainer Eric Musgrove in the first aid room at Cheltenham in South Australia in 2002.

Q: What was your biggest thrill during your riding career?

Wynne: The National. I won the National steeplechase at Flemington towards the end. And one of the biggest ones was at Oakbank, the Great Eastern, for Stan Craddock. It was my first ride around there and I won it. And then I ran that many placings in it after that. In the second year, the horse I won on, old Mystic Moon, he was a mile in front going further ahead, got to the second last, jumped it and tripped himself over. I got back on him and ended up running third.

Kevin Wynne with Gypsy Grey in 1974.

Q: You won the Grand Annual at Warrnambool twice, on Blueholme, for Stan Craddock.

Wynne: “We were going for three in a row when we lost him. He fell at the second jump and had to be put down. He’d never made a mistake really, he was a good jumper. He just made the one mistake, good jumpers only make one mistake.

Q: You love your racing. Do you follow the jumps racing nowadays?

Wynne: Yeah, I always watch them, keep an eye on them.

Q: Warrnambool...it’s great socially.

Wynne: It is. We used to go down there for the week and by gee we’d have a real ball, a real good time. And anyone who doesn’t enjoy themselves there, they’re hard to please I can tell you. We’d book into the caravan park there.

Kevin Wynne flies over the shoulder of Larkway during the Von Doussa Steeple at Oakbank in 1986.

Q: Working as clerk of the course, who has been the nicest jockey to deal with?

Wynne: Most of them, nearly all of them appreciate what you do for them. They’re all very good. I was doing it at the trots to start off with and then I got into the thoroughbreds.

Wynne winning on Topaven in 1986.

Q: When are you going to hang up the saddle?

Wynne: When I can’t walk. I enjoy what I’m doing and I’ve worked all my life. I got lost when the COVID came out and I wasn’t allowed to work. I had 12 months when I wasn’t working. And it was driving me mad. I’ve loved horses all my life and they’re all good. They are like people, you can get slow ones and you can get the fast ones.

Q: Where did you grow up and where did you go to school?

Wynne: Korumburra. It hasn’t really changed at all.