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Ad Brew defied the odds as a longshot, coming from behind to claim a memorable victory that cemented his legacy in racing history and provided Kerrin McEvoy with his first Cup success.

Their legend lives on

22 October 2025 Written by Celia Purdey

They’ve all won the race that stops the nation, and now Brew, Prince Of Penzance and Twilight Payment are winning hearts at Living Legends. These champions continue to inspire as they mark 25, 10 and 5 years since their Melbourne Cup victories.

At Living Legends, champions of the turf are still celebrated long after their racing days are over. Set within Woodlands Historic Park in Melbourne’s north, the sanctuary is home to 42 horses, each with a story that has shaped racing. For visitors, it is a rare chance to meet Melbourne Cup heroes and Group 1 stars up close, in a place where their legacies continue to live on.

Retirement here doesn’t mean the end of activity. Many horses remain in light work under saddle, keeping them active, healthy and engaged while showcasing their versatility beyond the track. Santa Ana Lane, the brilliant five-time Group 1 sprinter, has taken to dressage and even small jumps, drawing crowds at Off the Track carnivals. Johnny Get Angry, the 2020 Victoria Derby winner, enjoys trail rides and steady exercise, while 2020 Melbourne Cup victor Twilight Payment is equally happy on the bridle, often spotted on rides through Woodlands Park. These activities are not about competition but about wellbeing – offering stimulation, purpose and new ways for the horses to connect with people.

Brew

Brew

Prince of Penzance

Prince of Penzance

Twilight Payment

Twilight Payment

This year, three Melbourne Cup winners at Living Legends – Brew, Prince Of Penzance and Twilight Payment – mark milestone anniversaries. Their victories are etched into Cup folklore, and today they enjoy a quieter rhythm of life under the care of CEO and head vet Andrew Clarke and his dedicated team, including veterinary nurse Molly Stewart. Stewart first arrived as a student placement and “never really left.” Although she grew up on a farm, she didn’t work with horses until her degree and her time at Living Legends. She quickly fell in love with the residents and soon discovered the impact they had on people. “Some visitors come just to pat a horse, but others are in awe and totally starstruck,” she says. “They might want to meet the horse that won them money, or the one that reminds them of a special Melbourne Cup.”

For Stewart and her colleagues, the day begins at 8am with feeding and health checks for all 42 residents, followed by paddock cleaning and daily visitor tours, which they run. A typical day might see Stewart also treating minor injuries, managing medications and spending time simply interacting with the horses. She also accompanies them to events and back to the races.

“When we take them to Flemington, their ears prick at the sounds, and they watch the racehorses. They still remember – and they still love it.”

Brew – Melbourne Cup 2000

When Brew crossed the line first in the 2000 Melbourne Cup, it was a story of patience and persistence. Trained by Mike Moroney and ridden by a young Kerrin McEvoy in his first Cup ride, Brew had been a longshot, starting at 15/1. His staying strength and late surge made him the toast of Flemington and gave Moroney and McEvoy a career-defining moment.

Now 31, Brew is the “old man” of Living Legends, yet Stewart says “he doesn’t act like it.” Despite being the oldest horse on the property, he is still full of energy, often seen galloping around his paddock. He shares that paddock with another crowd favourite, Apache Cat (aka Patch), and the two are inseparable. “They actually get separation anxiety if they’re apart,” Stewart said. 

As a senior horse, Brew requires a little extra care. He is fed three times a day instead of two to help maintain his weight, rugged to regulate his temperature, and watched closely for any signs of age catching up.

Prince Of Penzance – Melbourne Cup 2015

Prince Of Penzance’s 2015 Cup victory is etched into Australian sporting history, not only for the horse but for the rider. With Michelle Payne aboard, he defied odds of 100/1 to become the first horse at those odds to win since 1940 – and, more importantly, carried Payne into the record books as the first female jockey to win the Cup. Her post-race declaration – “They think women aren’t strong enough, but they can get stuffed, because we just beat the world” – was as powerful as the victory, turning the triumph into a moment of inspiration.

Now 16, ‘Prince’ has mellowed into what Stewart calls “a cutie.” On the farm, he often stands at the fence waiting for cuddles, pats and carrots, loving the visitors’ attention. He also seeks the attention of his Cup-winning rider and has a bond with Payne that is still unbroken. “When he sees Michelle, he perks up straight away. He definitely still remembers her,” Stewart said.

Molly Stewart, Living Legend's vet nurse, feels lucky to work with such beautiful animals.

Twilight Payment – Melbourne Cup 2020

Twilight Payment’s 2020 Cup win was remarkable not just because it was run at an empty Flemington during the pandemic, but also for its execution. Trained by Joseph O’Brien in Ireland and ridden by Jye McNeil, the then eight-year-old stayer set a strong pace early and refused to give in, leading from start to finish.

Today, at 12, Twilight Payment – affectionately known as Twiggy – still carries the small, powerful frame that made him such a durable stayer. “He looks like a pony,” Stewart says, describing him as cheeky, quirky and full of character. He is also her favourite. “He’s super cute, and a little impatient sometimes, but that just adds to his charm.”

Twiggy remains active and kept in light work to maintain his fitness. He enjoys trail rides through the park, some light jumping and occasional appearances under saddle at Off the Track events. He recently stepped out into the show ring, competing in the Fashions on the Field in-hand section (sponsored by the VRC) at the Off The Track Carnival at Boneo. His handler and partner on the day, Living Legends Operations Manager, rider and retrainer, Adele Ioannou, agrees with Stewart, calling him “the cutest little horse that we have on the farm.”

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