Hollywood megastar Matt Damon experienced a disappointing result in Australian horse racing over the weekend, as his part-owned three-year-old gelding Are You Kidding was comprehensively beaten in the prestigious Australian Derby at Sydney's Royal Randwick racecourse on Saturday.
Distant Finish for Celebrity-Owned Runner
The bay gelding, which Damon co-owns with former Australian Test cricket captain Steve Smith and retired Australian Football League great Tom Hawkins, could only manage an eleventh-place finish in the classic race. Are You Kidding finished more than nineteen lengths behind the eventual winner, Green Spaces, in what proved to be a challenging contest for the celebrity-owned runner.
Notable Absence from the Racetrack
Unlike his appearance at the Golden Slipper event at Rosehill Racecourse last month, Damon chose not to attend the Australian Derby in person. The Oscar-winning actor had been present trackside for the earlier Sydney racing carnival highlight, but was absent as his horse contested the Derby distance.
This marked a contrast to his visible involvement in Australian racing circles, where he has been quietly building connections over recent years. Australian actor Daniel MacPherson also holds a stake in the ownership group for Are You Kidding, which is trained by the partnership of Paul Messara and Leah Gavranich.
Previous Racing Success Down Under
The Australian Derby disappointment follows a more positive racing experience for Damon earlier this year. In January 2025, another horse part-owned by the Hollywood star, named Dale, broke its maiden status with a victory at Tamworth racecourse.
That success marked Damon's first win as a horse owner in Australia, with the three-year-old gelding earning more than thirty thousand dollars in prize money after previously placing twice in earlier races. The horse is also trained by the Messara and Gavranich partnership.
Personal Connection Behind Horse Names
The naming of Damon's successful horse carries a particularly personal story. Trainer Paul Messara revealed during an interview that the unusual name originated from a late-night telephone call from Los Angeles.
"It's a bit of a long story really," Messara explained. "It was a late night over in LA and I get a phone call saying we've had this great idea and we want to buy a horse, but the stipulation is it must be called Dale."
Messara elaborated on the sentimental background, noting that Damon and his daughter had bonded during her teenage years while watching the comedy film Step Brothers, which features characters named Dale and Brennan.
Growing Australian Connections
Damon's increasing involvement in Australian horse racing reflects his broader connection to the country, where he has spent extended periods with his family and developed numerous friendships. The actor regularly visits Byron Bay, where his longtime friend Chris Hemsworth resides, and has become a familiar presence at various Australian events ranging from Australian Football League matches to Brisbane's Ekka exhibition.
The actor's relationship with Australia began during a significant personal period following the passing of his father, Kent Damon, in 2017. "After my dad died, we moved down there for four months and just went and camped all over the place," Damon recalled in previous comments.
"And just ... I think because maybe he had never been, and it just felt like a place to go to make memories with my kids," he added, explaining the emotional significance of his Australian visits.
Annual Australian Ritual
These Australian trips have since evolved into an annual tradition for Damon, his wife Luciana Barroso, and their four daughters. The family frequently chooses to spend the American summer months in Australia, maintaining strong connections despite geographical distance.
"Then every year we would return, even back during the pandemic. We were down there for about six months, and it's just like a second home to us," Damon has said. "We just love it and we love the people and everything about it."
The actor emphasized the depth of his Australian relationships, noting: "We just have so many friends down there, honestly. I mean thirty, forty people. Family, friends, just so many people that we love to go see."
While his racing venture experienced a setback at Royal Randwick, Damon's multifaceted connection to Australia continues to strengthen through both sporting investments and personal relationships.
