The Connections

Tony Ottobre is the owner and driving force behind Cape Schanck Stud, the Mornington Peninsula breeding and racing operation that races Pride of Jenni.

A successful businessman before turning his attention to thoroughbreds, Ottobre has built Cape Schanck into one of the most consistent small scale ownership operations in Australian racing, with a particular focus on buying well-bred fillies and mares at the yearling sales.

Ottobre's standing in the community extends well beyond the racetrack. Tony and Lynn began a sustained pattern of giving back in 2015, in the wake of Jennifer's death, donating more than $300,000 across dozens of GoFundMe fundraisers in the decade since, most of them supporting brain tumour patients and their families.

That generosity reached a new scale in April 2023, when Tony organised a fundraiser for Lucy Holland and her four children after her husband, jockey Dean Holland, died following a race fall; unable to find an existing appeal in the hours after his death, he started one himself, which went on to raise almost $2 million and was named Australia's biggest individual GoFundMe campaign of the year.

It was Ottobre who signed for Pride of Jenni at the 2019 Inglis Classic Yearling Sale, paying $100,000 for the daughter of Pride Of Dubai out of the O'Reilly mare Sancerre. The purchase reflected his long-stated preference for fillies with strong maternal pedigrees, and a price he has since described as one of the best-value buys of his ownership career.

Pride of Jenni carries the same sky blue and purple diamond silks as the rest of the stable's "Jenni" horses, a string of around 95 racehorses named in memory of Ottobre's daughter Jennifer. Ottobre has spoken openly about how naming and racing horses in her honour has helped the family process their grief and stay connected to her memory, a tradition that began the year after her passing and has grown into a defining feature of the stable's identity.

Ottobre's most consequential decision in Pride of Jenni's career came in 2022, when he moved her from an earlier trainer to Ciaron Maher's stable after she had struggled to reproduce her undoubted ability at black-type level. The switch transformed her into a front-running Group 1 winner within a year, and Ottobre has since overseen every major turning point in her story, from her breakout Flemington double in 2023, through the decision to retire her after a bleeding attack in late 2024, to the call to bring her back into work in 2025 when it became clear she wasn't ready to leave racing behind. He has said his approach to ownership is about presenting his trainers with horses in the best possible condition to do their job, and that for him and his family, the enjoyment of being involved in racing has always mattered more than the prizemoney.

Ciaron Maher is the trainer behind Pride of Jenni's transformation into one of Australia's most celebrated racehorses and one of the most successful and prolific trainers in the country. He began his career in racing as a jumps jockey in Victoria, even captaining the Australian team in the International Jockey Challenge against Ireland, before recognising that his physical size would limit his prospects in the saddle and turning his focus to training instead.

Maher built his education from the ground up, working alongside some of the sport's most decorated names, including Hall of Fame trainer Bart Cummings and international figures such as Aidan O'Brien and Willie Mullins before establishing his own stable with just six boxes on his family's property. From that modest start, he has grown Ciaron Maher Racing into a national operation spanning major training centres in Ballarat, Cranbourne, and Warwick Farm in Sydney, overseeing hundreds of horses and a large team of staff across multiple states. Between 2018 and late 2023 he trained in partnership with David Eustace, a period that produced some of his biggest results, including the 2022 Melbourne Cup with Gold Trip, before resuming sole training duties under his own name when Eustace relocated to Hong Kong.

Maher took over Pride of Jenni's preparation in 2022 at the request of owner Tony Ottobre, after she had shown promise without consistently delivering at black-type level under previous trainers. By his own admission, he didn't initially expect her to develop into the horse she became; what he did identify early was a mare who needed an individualised approach, given her sharp, sometimes difficult temperament both at the trials and on the training track. Working with his stable team, including the daily care provided by strapper Sammy Waters, Maher reshaped Pride of Jenni's racing style around aggressive front-running tactics that played to her strengths — an approach that delivered four Group 1 wins, the 2023/24 Australian Racehorse of the Year title, and a career resurgence in 2025 that few in racing expected to see.

Declan Bates is the Irish-born jockey most closely associated with Pride of Jenni's rise, having ridden her to the majority of her biggest wins. Raised around horses in County Wexford, Ireland, Bates began his career as a jumps jockey in the point-to-point ranks before injuries prompted a switch to flat racing, first in Britain and then, seeking better opportunities, in Australia. He has built a long and respected career since relocating, riding several hundred winners and forming key partnerships with Australian stables and owners along the way.

Bates' history with Pride of Jenni stretches back further than most fans realise. He first partnered her years before her transformation, in a Group 2 at Flemington while she was still with an earlier trainer, finishing narrowly beaten in a run that hinted at ability not yet fully realised. It wasn't until owner Tony Ottobre recalled that performance, after Pride of Jenni had moved to Ciaron Maher's stable, that Bates was given the ride that would define his career. The partnership produced four Group 1 victories together, including both of her TAB Empire Rose Stakes wins and her extraordinary 2024 Queen Elizabeth Stakes triumph at Randwick, a front-running demolition job widely regarded as one of the standout performances in modern Australian racing.

Bates lost the ride in late 2024 after a below-par run in the Cox Plate, with connections opting for a change before Pride of Jenni's retirement was announced shortly afterwards. When she returned to training in 2025, it was Craig Newitt who partnered her for her comeback win, but Bates was reunited with the mare later that year for his Group 2 Feehan Stakes victory and her remarkable repeat win in the TAB Empire Rose Stakes — making her the first horse in 35 years to win the same Group 1 on Derby Day in different years. Bates has described his association with Pride of Jenni as a career-defining partnership, and has spoken about the close relationship that has developed between his family and the Ottobres through years of racing the mare together.

Sammy Waters is the strapper who has cared for Pride of Jenni on a daily basis since the mare first arrived at Ciaron Maher's stable in 2022, and is widely credited by connections as one of the key reasons behind her transformation. Based primarily at the stable's Cranbourne facility, Waters took over Pride of Jenni's day-to-day handling from the moment she walked through the gates, building a relationship with the notoriously sharp mare that owner Tony Ottobre has pointed to as a turning point in her temperament and form.

Under Waters' care, Pride of Jenni's behaviour around the stable changed noticeably: she no longer required a stallion chain or ear muffs to settle, and stopped needing the clerk of the course to lead her to the barriers on raceday — small but telling signs of a horse who had grown to trust her handler. Waters also rides Pride of Jenni in her daily trackwork, working closely alongside Cranbourne-based assistant trainer Jack Turnbull and the rest of the stable's hands-on team to prepare her for raceday.

Often the first to greet Pride of Jenni after a win and a constant presence around the stable, Waters represents the part of the Pride of Jenni story that rarely makes the form guide — the daily groundwork, patience, and trust-building that underpins every result achieved on the track. Trainer Ciaron Maher has singled out Waters, alongside Turnbull and Tony Ottobre, as central to the courage and care it took to keep Pride of Jenni's career going through its toughest stretches.