As a younger man, Ottobre dreamed of success in the saddle. Admittedly built like a jockey, he had the courage and the will, but by his own recognition he lacked the talent to make a career of it.

“I was an apprentice and rode for about four years. I rode for Pat Bourke at Flemington, leading Victorian trainer Brian Courtney, and Bobby Winks, I think I ran third once. I was far from the best, but I gave it a good go,” he said.

“I ran into Colin Hayes one morning at Flemington and he invited me to Lindsay Park at Angaston to ride work and help with breakers and race-day strapping duties. It was an amazing experience and I learned from him that in life if you do the best, the best will come to you. It’s a lesson I’ve always remembered.”

Although forever bitten by the racing bug, Ottobre moved away from the sport in the late 1970s and into the automotive industry where he set about learning a new trade.

“I got into LED lighting for trucks, trailers and buses and started a business called LED Technologies. Over time we grew to become the number-one in our field in Australia, and during Covid we were approached by a big firm from the US who put forward a potential buy-out,” he said.

“It was a big opportunity. Lynn and I discussed it and thought why not, it would give us the opportunity to really have some fun and invest in our passions, and after what we’d been through as a family that made a lot of sense.”

In 2015 Ottobre, his wife Lynn and son Michael were left utterly heartbroken by the death of daughter and sister Jennifer, who tragically lost her battle with brain cancer.

Given a bleak outlook of a nine-to-twelve-month life expectancy when first diagnosed, Jennifer fought bravely and lived for another four years, marrying her husband Luke in the months before she passed away. It was a challenging but inspiring time for the family, and a reminder that life should be enjoyed and celebrated.

As a tribute to Jennifer’s memory, the Ottobres named a young High Chaparral filly Jennifer Lynn after their daughter. On the day the filly became their first stakes winner when winning the Listed Lexus Hybrid on Melbourne Cup Day in 2016, they took a rainbow on the morning of the race as a sign that Jennifer approved.

In a position to expand their racing interests following the sale of LED Technologies, that tribute quickly grew to a team of 30 horses, most of whom carry Jenni as a part of their name.

“When you lose a child, it’s totally devastating. What gave me comfort during that time was the horses, so we decided we would name our fillies after Jenni. As a family it bonds us and brings us closer together, we can remember her and celebrate her,” he explained.

Fast forward a few years to the 2019 Inglis Classic Sale and the Ottobre’s Cape Schanck Stud secure a filly by Pride Of Dubai from the O’Reilly mare Sancerre for $100,000. Bred by Brent and Cherry Taylor of New Zealand’s famed Trelawney Stud, the filly certainly had the background to make it on the racetrack.

Naming the filly, who would eventually become Pride Of Jenni, was always going to be the easy part, easier though for Ottobre was the decision to buy her.

“When it comes to buying a horse, I put a lot of weight on the influence of the mare. I love Zabeel, High Chaparral, O’Reilly, and Pride Of Jenni has both Zabeel and O’Reilly there on her dam side, and she came from one of New Zealand’s best breeders, so I was immediately interested in her. On type she looked like a filly that would get a mile and further and that’s what I love to race. For me she was perfect all over,” he explained.

But despite showing early promise and winning two of her first five starts, coaxing a Group 1 out of the mare was a little more difficult and would require a couple of changes of environment.

“We started her with David Brideoake and then Symon Wilde before we moved the mare to Ciaron (Maher) and Dave (Eustace). Nothing against David or Symon at all, they are very good trainers, but I made the decisions in the best interests of the mare at the time. I felt that she wasn’t giving us everything she had, I wanted to try and find the key to her. For me, the horse always comes first.”

The decision to relocate Pride Of Jenni for a third time would prove to be an inspired one. A winner at her second start for Maher and Eustace, Pride Of Jenni had found her happy place, with a nose second place in the Group 1 Coolmore Classic in March last year a sign that she had gone to a new level.