OFF THE RECORD #111
Jeffrey Syster: A Breakthrough Built The Hard Way
Read moreJeffrey Syster: A Breakthrough Built The Hard Way

Above: Kingsmead wins: “It was going to be easy after this, but it wasn’t!” (image: Candiese Lenferna)
Jeffrey Syster’s first ride as an apprentice ended in victory. On 25 May 2019, aboard a sprinter named Kingsmead, trained by Michael Roberts, he came from last to first in a handicap over 1000m at Hollywoodbets Scottsville for a fairytale start to the then 19-year-old’s career.
Last Saturday, Syster claimed his first Grade 3 success on Mike and Mathew de Kock’s Miami Mountain, again delivered with a sweeping late surge, this time over 1100m. But the meaning was very different. It was a reward for seven years of graft – sweat, early mornings, missed opportunities and lessons learned the hard way.
“I was overwhelmed on my first day,” Syster recalls. “I’d won a race for the legendary Mr Michael Roberts and was riding against some of the best in the country. Anton Marcus, Muzi Yeni, Richard Fourie and Warren Kennedy were all in the race.
“Kingsmead was last, but he started picking up at the 350m. I’d been taught to shout, ‘I’m coming through!’ – which I did. We switched out, found a gap and he won in my hands. I remember thinking afterwards, ‘Well, that was fun… this is going to be easy!’”
He laughs now at the memory.
“The reality is I had no idea how we’d actually won it. For most of the race I was just trying to stay safely in the saddle and keep Kingsmead running straight and out of trouble. But he was in charge. He pulled me through, guided me into the challenge. We got lucky in the last 100 metres. I probably sounded like I was wounded and calling for an ambulance. The big guys around me must have had a chuckle!”

Above: With riding master Robert Moore: Highveld Champion Apprentice in 2022/23. (Image: supplied)
Syster rode a respectable 70 winners as an apprentice, but the professional ranks have a way of exposing weaknesses and humbling even the most promising youngsters.
He explained: “One of two things happens to apprentices when they come out of their time. They either carry their winning momentum into the senior ranks, or they have to start from scratch. There’s no middle ground.
“Take Kabelo Matsunyane, Philasande Mxoli and MK Katjedi. They left the Academy in good form and kept it going straight away. I wasn’t getting the rides, so I lost patience and took an opportunity in Bahrain. In doing that, I lost the chance to build momentum locally. When I came back, I had to start from the bottom.”
While he gained valuable international experience and rode two winners during his stint in Bahrain, Syster’s career almost stalled upon his return to South Africa. “The competition for rides is fierce,” he explains. “When you get a single opportunity and don’t quite meet expectations, you’re back to square one.”
Syster took a few rides in Zimbabwe, struck up a good partnership with trainer Debra Swanson and has ridden 66 winners at Borrowdale Park in the last three years, clinching the Jockeys’ Title in 2022/23. He commented: “There are only a handful of stables now and the fields are small, but it’s worthwhile going because it presents more chances to work on my riding skills and judgement of pace.”
Taking a step back, he realised that being a jockey is, in many ways, no different to operating in any other competitive profession. It is a business built on relationships.
“Trainers are set in their methods and routines, and they warm to familiar faces. It takes time to get to know them and build that connection. There was one trainer who didn’t greet me at the track in the mornings for almost a month, but I kept showing up and rode a few of his runners every morning until he had no choice but to say hello. It’s much better now, we get on well and discuss his horses.
“You build trust and mutual respect by showing up and doing your best – not once or twice, but every day. However long it takes. I go to Mr Pettigrew (Stuart) at 5.30am. He and Mr Azzie (Michael) work their strings first, and then I run along to as many other trainers that I can get to – Mathew de Kock, Sean Tarry, Alec Laird and others.”
Syster believes that approaching his profession from a relationship perspective also makes it easier for trainers to address mistakes without emotion clouding the conversation.
“When you’ve ridden what they see as a poor race, or when you haven’t followed instructions for whatever reason, some trainers won’t even talk to you. They won’t give you another ride, and they just shut you out. But when there’s a cordial, professional relationship in place, they’re far more willing to sit down and discuss what went wrong and how to fix it. They don’t close the door on you.”

Above: This young striker was just too small! (Image: supplied)
The blade of grass that first broke the surface in 2019 did not shoot up overnight, as Syster had to deal with an earlier setback. He said: “I joined the Academy at 19, just made the age cut. This was a relatively late start because I’d always had my sights set on becoming a professional soccer player. I was pretty good as a striker and on the wing in my school teams, so after school I decided to try out for Orlando Pirates and Chippa United, but with no luck.
“They told me I was good enough, but just too small. I was almost 20 years old and weighed only 46kg. I was deflated, but my uncles were keen punters and one day one of them looked at me and said, ‘Jeffrey, you should be a jockey!’ I’d never sat on a horse or watched a race, but a few weeks later and I was enrolled, and my life took a new direction.”
Syster has added only 4kg since those soccer days, and his natural riding weight is 50kg. To maintain it, he eats just one small meal a day, focusing on protein – much like Andrew Fortune, as noted in OTR105. “Consistency is all that matters,” he said. “I restrict my meals and go to the gym regularly.”
Every now and then he allows himself a proper meal and jokes: “When Piere Strydom is in town, I invite him to lunch – but I make sure he pays!”
Strydom has been generous with his advice since retiring, and Syster regards his guidance as invaluable. In the Jockeys’ Room, too, there is a strong sense of camaraderie. He said: “They’re a good bunch of people. We help and learn from one another. Everyone has something different to offer.”
Syster’s 10 most recent winners have returned runners at 33-1, 25-1 and twice at 14-1, producing an average starting price of 12.5-1 – which shows that he is making the most of the opportunities presented to him.

Above: Jeff with De Kock Racing’s assistant trainer, David Lhamini (Image: JC Photos)
Two of those victories came for the high-profile De Kock stable, where Mathew de Kock speaks highly of the jockey and echoes Syster’s emphasis on consistency and hard work. “He has a good work ethic, he listens, and he doesn’t get a big mouth when he’s jocked off,” said De Kock. “He’s out there trying harder every day, and we like that.”
Syster hopes he will get the opportunity to partner Miami Mountain again. “He’s a good horse, the best I’ve sat on. We fitted blinkers for the National Currency Sprint to improve his focus. He was slow away again and still well back early, but he travelled better and got to his cruising speed much quicker.
“At the 400m he was still some way off them, but he was building into his run so strongly that I knew he’d go close. I was on the inside and couldn’t see right across the track, so I rode him right through the line. He was actually in front well before the post.”
Syster has secured the ride on the stable’s promising Yippee Kiyay in next week’s Grade 1 SA Classic and he said: “He went very quick when he set the pace in the Gauteng Guineas. We finished fifth that day, but maybe we can pinch the Classic. He’s a lovely horse because he wants to give you everything. Sometimes he feels the pressure too soon and goes flat out.
“I need to get him to relax and hold on a touch before he gets into top gear. He’s a tricky one because all he wants to do is go. He doesn’t really pull. He’s just keen to compete. If I can get the balance right with him, he could surprise.”
Syster does not employ an agent. He studies the nomination sheets and manages his own bookings. “I phone trainers for rides,” he quips. “I’ve never had a trainer phone me to ask if I’ll ride one. That’s something I secretly hope for. The day that happens, I’ll be smiling!”