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SA Raider: Clare Lindop reflects on the Derby long-shot that shocked Flemington

Jockey Clare Lindop and trainer Leon Macdonald remember Rebel Raider, the colt who in 2008 became the longest-priced winner in Victoria Derby history.

When Clare Lindop steered Rebel Raider to an upset victory in the 2008 G1 VRC Derby, the $910,000 winner’s cheque wasn’t the only prize earned. 

Returning to the Flemington scale the winner of one of Australia’s most enduring classic races, the vertical black and white striped silks Lindop wore that day were a symbol of a journey that began with a Warrnambool apprenticeship and culminated in three South Australian metropolitan jockey premierships. 

“Racing is one of the first sports to ever embrace females and males competing together on equal footing, with no advantage or quarter given,” Lindop told Asian Racing Report. 

“You’ve got to earn your own stripes and everyone is judged on their merits, and I’m proud to have operated and achieved success within that framework.

“I think we’re often criticised in the industry for being chauvinistic but I’d have to disagree.”

For Lindop, a jockey remembered for a series of ‘firsts’ on the racetrack – the first Australian woman to ride in the Melbourne Cup, the first Australian woman to win a Group 1 race, the first female jockey to win a metropolitan premiership and the first female to register 1,000 wins  – the only firsts that truly mattered were those punctuated by a finding of ‘correct weight’.


Clare Lindop scores on Dolphin Jo on Caulfield Guineas day, 2008. (Photo by Quinn Rooney/Getty Images)

Any achievements attached to her gender, however, were – and still are, although the stance is somewhat softening – considered largely immaterial. 

“I probably didn’t have a great relationship with the media and should’ve been smarter about it, because they would always ask me about being a female jockey and I’d say ‘I’m just a jockey’,” Lindop recalls.

“I guess if you speak to any female athlete it’s the same story. They want to be known as a ‘footballer’ not as a ‘female footballer’, or they want to be known as a ‘jockey’ not as a ‘female jockey’.

“But I guess on reflection now it’s something I’m pretty proud of, and what I’m most proud of is that when women succeed in this sport it doesn’t even make headlines anywhere because it’s not considered to be news anymore.” 

Lindop cites the recent ascension of record-breaking Tasmanian apprentice title winner Cody Jordan, and the continued successes of Jamie Kah, as evidence of a shift in perception. 

“When Jamie Kah rides the favourite in the Caulfield Cup, it’s not even mentioned that she’s a female jockey. So I think in some ways that’s the most satisfying part for me, when women are just considered as athletes and not in terms of their gender.” 

Jamie Kah and Smokin' Romans. (Photo by Vince Caligiuri/Getty Images)

Rebel Raider – with the determined Lindop booked to ride and a border-crossing Derby plan hatched – could scarcely have been better named. 

A $150,000 Magic Millions purchase for trainer Leon Macdonald, the colt by Reset – an undefeated G1 Australian Guineas winner and son of Zabeel – out of G1 Flight Stakes runner-up Picholine came equipped with a quality pedigree. 

But for Macdonald, it was that same pedigree – coupled with victory in Morphettville’s G3 Sires’ Produce Stakes as a two-year-old – that proved problematic for the horse’s career trajectory. 

“After he won the Sires’ in Adelaide the owners wouldn’t geld him,” Macdonald told Asian Racing Report.

“But from my point of view, the horse badly needed gelding because he was very heavy. Anyway they wouldn’t do it and in a way it contributed to his undoing as he just got too heavy in front.” 

Before injuries started to take their toll Rebel Raider demonstrated serious talent on the track, proving himself a versatile staying horse with an impressive turn-of-foot. A rare mix made even rarer, according to Macdonald, by the entire’s best physical attribute: his lungs. 

“His breathing was just so good, he’d never blow a candle out when he pulled up after work,” said Macdonald. 

“When you listen to other people, for instance Glen Boss when he won the (Melbourne) Cups on Makybe Diva, he couldn’t get over the way she breathed either. 

“These good breathing horses, even if they’re ordinary, they run to the best of their ability, so if you add natural talent into the mix you’ve got a very good racehorse.”

Rebel Raider’s springboard into the VRC Derby came via the 2200-metre Geelong Derby Trial (now the Geelong Classic), a lead-up race traditionally favoured by some of the ‘lesser lights’ of the season’s staying cohort. Sent out a $12 chance at Geelong with Lindop up, Rebel Raider finished a well-beaten third after overracing. 

Though not a frequently called upon aid for a horse stepping up in trip, Macdonald was confident a gear adjustment would have his colt primed for the 2500m of the Derby. 

“At Geelong he didn’t concentrate at all, he was looking around everywhere and he didn’t go to the line as well as he should’ve, so we elected to put blinkers on him for Flemington,” Macdonald said. 

Standing in Rebel Raider’s way would not only be dominant Caulfield Guineas winner and raging favourite Whobegotyou, but pretty much all 13 of the other three-year-olds set to face the starter. Of his opposition that day only two horses jumped at a bigger price than Rebel Raider’s 100-1. 

But having had plenty to do with Rebel Raider since the big, rangy two-year-old with a stack of potential first entered Macdonald’s stable, Lindop had been satisfied with Rebel Raider’s effort at Geelong, and went in to Flemington with an open mind, if not a degree of confidence that belied her mount’s odds.

“You get a young horse like that and then you earmark them for their three-year-old season, you set high targets for a lot of these three-year-old horses on Derby or Oaks preparations, and it’s really exciting when it actually comes to fruition and they develop and reach their potential,” she said.

And it was the gear change designed to bring Rebel Raider’s focus back on the job at hand that unlocked that early potential, and spectacularly so. 

“The blinkers obviously proved successful and he raced really well in the Derby,” remembers Lindop, who had the added responsibility of overcoming barrier 15 of 15. 

“I was able to settle him and then he was full of running in the race, and I was able to push out at the top of the straight and that was always the plan, to make it a true staying test. We believed he was the best stayer in the race and he proved it, he was just so dynamic at the finish of the 2500 metres.”

Whobegotyou battled home into second but was no match for the visiting South Australian’s powerful finish, and bookmakers weren’t the only ones cheering as Rebel Raider became the longest-priced winner in Victoria Derby history. 

Lindop, who had left school at 14 to pursue a career in the saddle, had two of her biggest supporters watching on in the stands. 

“My parents were there. When I think back to when I was a kid who left school, and Mum and Dad used to take me to work at 4am, even throughout my career they’d drive me to far-flung tracks when I couldn’t get other jockeys to take me,” Lindop said. 

Learning her craft first in the south-western districts of Victoria had allowed Lindop to extensively ride the South Australian border, including Mount Gambier, Naracoorte and occasionally in the Adelaide metropolitan area. So after outriding her country claim, Adelaide felt like the right fit for the country kid: “I was only coming for three months and ended up staying for the rest of my career.” 

VRC Derby glory for Clare Lindop and Leon Macdonald. (Photo by Quinn Rooney/Getty Images)

“There were a lot of people that believed in me and had given me these opportunities, with Leon Macdonald being the key component of that, he had mentored me as a rider.

“To take me to the race and have the support of those owners and having the confidence that they were going to allow me to be the best jockey I could be on the day, that they trusted me to do as I saw fit on Rebel Raider, and to have me pull off a plan – basically raid the money from Victoria and bring it back to South Australia – was just really joyous, and incredibly satisfying to think that all those years of hard work had paid off. 

“There’s just so much that goes into those couple of minutes of performance for a racehorse – all the training, the setbacks, it’s a long road – so when you hit the front and have the composure to finish it off it’s extremely satisfying.” 

For a horse so famously remembered for this Victoria Derby heist, it’s easy to forget that Rebel Raider won another Group 1 race, returning to his home state after a disastrous Sydney excursion to dominate his local Derby from the front, with Lindop again in the saddle. 

“He had a chip in his offside hock which couldn’t be removed, and when he went to Sydney he went terrible, he could not go the Sydney way of going,” said Macdonald. 

“But he was a very very good horse, except for injury he’d have got a lot further.” 

Macdonald – who in a highly distinguished training career has prepared other high class stayers in champion three-year-old Gold Guru and Caulfield Cup winning mare Southern Speed – retains an extremely high opinion of Rebel Raider.

“Ifs and buts are great in racing, but if he’d have been a gelding I think he’d have won a Melbourne Cup.”

For Lindop, the Derby victory was the second ‘life-changing’ moment she experienced at Flemington, having ridden a Macdonald-trained stayer named Debben who did make it all the way to a Melbourne Cup in 2003. 

“I was the third female to ever ride in the Cup, the first Australian, and that just changed my career overnight. I guess people thought ‘if she’s good enough to ride in the Melbourne Cup, then she must be able to ride’. 

“That season I went on to ride 111 winners, that was a record that only got broken recently by Linda Meech and Jamie Kah, so the confidence it gave me as a person and as a rider, and the opportunities that led to, were just phenomenal.” 

But for Lindop, who retired from riding in 2018, winning – not just competing – still resonates loudest. 

“Winning the Derby on Rebel Raider was my most prestigious achievement as a rider. Having a VRC Derby on my resume, it gave me a platform and opened so many doors for me. 

“Hitting the front at Flemington in a classic race, it’s hard to put into words that feeling that you get.”  




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