From the farm to the form and everywhere in between

On the morning of his first ride in a Melbourne Cup aboard Twilight Payment (Ire) (Teofilo {Ire}), jockey Jye McNeil reached out to his mentor Deane Lester for any last-minute advice. 'Be brave' came the reply.

McNeil's subsequent all-the-way success aboard Twilight Payment was hailed as one of the best rides in recent memory, and certainly one that was defined by bravery. Under instructions from trainer Joseph O'Brien, McNeil increased the tempo from the 1000 metre mark and one by one, his rivals wilted, leaving him clear to write his name in the record books as a Melbourne Cup-winning jockey.

The victory marked many milestones, including owner Lloyd Williams' seventh Cup success and young trainer O'Brien's second at age 27, but for McNeil and Lester it was the culmination of a plan 18 months in the making and three months in the execution.

Lester, renowned as one of the most astute form analysts in the country, had formed a friendship with McNeil through his good mate, and McNeil's first master, Gerald Egan, seven years ago. Early in 2019, McNeil had reached out to several influential people in his career and asked them to help him reach the next level as a jockey.

"When Jye first came to town, Gerald asked me to keep an eye out for him. Jye's first Flemington ride was for myself and Robbie Griffiths," Lester told TDN AusNZ.

"Over the last seven years, we have built that rapport and Jye approached me about 18 months ago and said he wanted to build a team around him where he could bounce ideas off, be they good, bad or otherwise. He asked if I wanted to be part of that team, and I said absolutely."

McNeil wanted to be better prepared ahead of raceday and working with Lester, was able to better communicate with owners and trainers about what he thought the best way to ride a horse was.

Partially due to his improved communication, greater opportunities began to flow for McNeil and in August this year, he was approached by Lloyd Williams to commit to riding one of his horses in the Melbourne Cup. Soon after it would be confirmed that horse would be Twilight Payment.

Two days before the Cup, McNeil had taken a long phone call from O'Brien, the horse's trainer, where the plan was hatched how the 8-year-old would be ridden.

"We'd been talking about the race and Jye had been taking in information for over six to eight weeks so there was a lot behind that. Joseph's finishing touch was that he had the backing of the stable to do that and that he had the horse to be able to do that," Lester said.

Lester watched on with great pride and great emotion on the first Tuesday in November as McNeil rode himself into history.

"When he hit the line, you knew that moment was going to change his life forever. To have a little role in that history, it’s very satisfying and I was very proud of him. He rang me on the Friday after Oaks Day and said 'I still can't believe it!'

"I said take yourself to Wikipedia and see your name next to all the other jockeys and that's when it gets real. When you realise the jockeys that haven't won it.

"I said 'There's a special award for the jockeys called the Scobie Breasley Medal. They named a medal after him and he never won a Melbourne Cup, and you've been able to do that'."

Returning the favour

It was a few months earlier, back in August, that McNeil was able to give Lester a huge thrill of his own. A Geelong maiden is a long way from the Melbourne Cup, but the feeling was almost as satisfying.

Stradari (Strategic Maneuver), a gelding Lester bred himself, won on debut for trainer Kevin Corstens with McNeil in the saddle. He is a grandson of the first city winner Lester's mother, Sandra Borschmann, ever trained.

"In 1987, my stepfather bought my mother a yearling, which ended up being called Spirited Rose. She was our first city placegetter and so then we bought her half-sister, who was a mare called Spiritdari, and she won at Caulfield and was our first city winner," Lester said.

Spiritdari (Toy Pindarri {NZ}) produced five winners from six runners, including Ladari (Ladoni {GB}), the dam of Stradari.

Like an expectant father, Lester confirmed that Ladari has a 45-day positive to Bel Esprit.

"The breeding side still gives you that extra kick. I've got pictures of Stradari from when he was on the ground first born. His whole life is there in front of me in photos. You get a huge buzz out of that," he said.

Another successful horse he bred was Kindrate (Pirate Army {USA}), who won five races, four in town, while he has also held ownership in a number of successful horses including Declare (Century), Go With The Flow (Gold Carat {USA}), Grand National Hurdle winner Busby Glenn (NZ) (Pentire {NZ}) and most notably G1 Newmarket H. winner The Quarterback (Street Boss {USA}).

A lifelong passion

The connection to owning and breeding horses takes Lester back to his childhood when his parents ran horse studs in Victoria, something which was clearly a formative aspect of his long association with thoroughbreds and racing.

"My family were involved in stud farms and we first had one at Dromana, where we stood a horse called Martello Towers, who was a Triple Crown winner in Sydney," he said.

"We then had a farm in Gembrook up in the Dandenongs where we had a son of Todman called Lomond, a Mornington Cup winner called Gay Marquis, and an import called Vaguely Familiar.

"The things I remember from that time the stallions and my Shetland pony. I also remember when I was five, we were foaling down mares. Things like that stick in your mind."

Moving with his mum to Langwarrin for schooling reasons after the separation of his parents, Lester was briefly taken into playing other sports like cricket and golf, but the lure of the thoroughbred was always there.

"My dad and his new partner got a property at Koo Wee Rup and she decided to train a couple of racehorses and I'd go there on weekends and I started riding them. I loved going from riding ponies to riding thoroughbreds," he said.

"I started strapping horses for them on weekends, and that taught me a lot, and then when I was 13, I had a chance to swap the pony I had for a mare. Her name was Lady Delina, and she won at Traralgon on Derby Day that year.

"That got me pretty interested then in the training side and the following year, Mum took out her licence and I used to ride one before school every morning."

Lester held ambitions to train horses himself, but ongoing health issues related to spina bifida, a condition he had since birth, saw that dream out of reach.

"I got quite sick in the third term of my HSC year and I didn’t complete my HSC and over the period of 18 months had had a few surgeries, and it was starting to look like I wouldn't be as hands on with the horses as I wanted to be," he said.

"I wanted to be in racing of some sort. I’d go up to Cranbourne every morning and watch and learn off people.

"The racetrack is such a fertile place to learn all the different angles. Whether it be the horses, whether it be the form, whether it be the punt, it’s an amazing place."

A new direction

On the week of his 21st birthday, Lester got a phone call which would change the direction of his career. The current clocker at Cranbourne had taken ill and the Sporting Globe wanted to see if he was interested in helping them out. He was barely in print when his career took a multimedia turn.

"I got a call from 3UZ, they said they wanted me to do a two-minute spot on Saturday morning on the best from the track at Cranbourne, so the day before my 21st birthday was the first time I was on radio," he said.

Soon after he developed a connection with a form expert, David Price, who is now based in Hong Kong. Through Price and his other racetrack connections, Lester learned the importance of knowledge, discipline and hard work.

"I was only required to do things at the Sporting Globe for Tuesdays and Thursdays, because they were recognised as the fast mornings but I would be there every day, looking at the horses, and take myself to the races every day I could," he said.

While building up his credentials as a form analyst, Lester had also built quite a rapport with jockeys, especially Simon Marshall, who had grown up around the corner and who he used to drive to the races.

Lester acted as a bit of defacto manager for Marshall and then fulfilled that role in an official manner for another good mate Peter Mertens for eight years. He also managed Luke Currie for six years early in his career.

As his media work expanded, Lester dropped off the jockey management, but maintained a strong rapport with the riders, and was asked by Egan to help mentor a young Nick Hall. Later on, another of the graduates from Egan's stable, McNeil, would also come to work closely with Lester.

That led him to his very proud moment on Melbourne Cup Day 2020, as McNeil demonstrated all the bravery Lester had asked of him to pull off one of the great Cup rides. It’s an experience Lester could never have imagined as a kid growing up on a stud farm, or as a 13-year-old doing his first bloodstock deal.

"It's given me things I never thought would happen. It’s not work for me. It’s been well said that if you are doing something you love, you are never really working, and it’s been a lot of fun," he said.

"There's a lot of hours to it, but whether it be the jockeys, whether it be doing the form for the media, whether it’s working out a program for a horse or looking at pedigrees, there are so many aspects of it. I have been lucky enough to have a little taste of all of those."