Michael Freedman was still in high school when the Freedman brothers emerged as a new force in Australian racing. Forty years later, the youngest Freedman is driving the latest chapter, with the help of his new assistant, Hall of Fame brother Lee.
On the racetrack, the story of the Freedman family has been one of peaks, troughs and timelines.
Lee Freedman’s recent announcement that he would relinquish his licence to become stable manager at the Gold Coast for his youngest sibling Michael drew focus on not just the career of Lee himself, but the complex story of the Freedman brothers.
For 57-year-old Michael Freedman, the youngest and a school kid when the four brothers marched into Leonard Crescent, Flemington in 1984, two events on the timeline stand out beyond all others.
The day wife Anna agreed to a move to Singapore in 2008 was pivotal – “you can’t assume your wife will agree to every career decision you make”.
Then there was September 5, 2017, when a horse walker tragedy at his Sha Tin stables left one horse dead, many injured and contributed to what Freedman assumes was “the shortest training tenure in Hong Kong history”.
The announcement in early March 2021 that Michael and Richard would part ways just days after winning the Golden Slipper with Stay Inside probably meant more to fans and media than it did Freedman. There was speculation of a rift, one that has never been completely quashed.
But no one is defined by career deeds alone, and for Michael Freedman, his life has featured two key events.
The first was the death of his father Tony, at age 55.
Tony Freedman died in 1984, just four months after sons Lee, Anthony, Richard and Michael left Warwick Farm for Flemington and before they’d achieved enough to do him really proud. Even now, it plays on Michael’s mind.
Tony had been a builder who cashed in on some land near Kiama, a coastal town south of Sydney. The proceeds allowed Tony to buy a farm at Yass and indulge in his passion for breeding and training to punt.
He imported a stallion from the United States called Loosen Up, who would produce not only David Hayes’ champion Better Loosen Up but also Sauna, Lee Freedman’s first good horse.
Tony never got to see Sauna or the other champions that flooded the Leonard Crescent stables. He died before his sons began their journey into racing folklore.
“Dad’s side of the family had a rich racing history. His grandfather Bill McLachlan rode three Melbourne Cup winners,” Michael Freedman said.
“He loved setting a horse up for a punt. Lee ran the farm at Yass and when Dad died, Lee basically stepped up.
“I often think about Dad and back in the early 1990s, when we had all those champions up at Leonard Crescent, we spoke about it a lot: 'if only Dad was around to witness what was going on'.”
“Looking back, we were basically kids. The first three years, from 84-86, I was still at school (at Melbourne Grammar).”
Seventeen years after the death of Tony Freedman, his youngest was about to become a father himself. There was a curveball.
The brothers had moved the entire team of horses to Caulfield and the winners had dried up. They were becoming claustrophobic in their own company.
“Looking back, neither of us really knew what our role was, we were getting in each other’s way,” Michael said.
Michael was in Sydney with some horses. Anna, who was pregnant, rang from Melbourne, where they lived in Armadale.
“Anna wanted me to come back for the 12-week scan. Her hormones were high and we were told there was a chance we were having twins,” he said.
“We went to the doctor, and he sort of hesitated. We started freaking out. What’s wrong? He said, ‘no, nothing wrong, you’re having triplets’.
“I burst out laughing for some reason, but Anna grasped straight away what was ahead and burst into tears. We’d have to get a bigger house, a bigger car and all that but that was nothing.
“They were born eight days before September 11, 2001. They spent the first three months of their life in hospital. They were very premature; tiny, six pounds in total, connected to machines. We’d get phone calls from doctors and we’d be like ‘my God have they stopped breathing?’
“It was a nerve-wracking time. But the other boys were either dads or uncles at the time and they were extremely supportive.
“We’d had ups and downs as trainers and we were definitely in a slump at the time but nothing in my life ever compared to that time, constantly thinking what may have gone wrong with the triplets. It took a full six months to get out of the woods.”
The stable had also been in the wilderness; unusual and frustrating for an operation that had smashed through like a wrecking ball. The revival would take more than six months.
The successful Markdel era followed. The Mornington Peninsula property was named in honour of Mum Del and a fifth brother, Mark. It was the era of Makybe Diva, Mummify and Miss Andretti.
Anthony had stepped up as assistant to Lee and Michael was beginning to get the itch.
In 2008, he was granted a licence to train in Singapore. First, he’d have to check with Anna. By then, the triplets were aged six.
“They were still very young. I had to sell the idea to my wife. We had a nice barn on the Mornington Peninsula, a nice life, but I was about to turn 40 and I didn’t want to die wondering,” he said.
“We packed up a comfortable life. Fortunately, I have a wife who has always supported my nomadic habits. Plenty of wives would baulk at uprooting three young kids.”
The Freedman name did not necessarily open doors in Singapore.
“I had eight very enjoyable years in Singapore. I learned a lot. I had to stand on my own two feet, it wasn’t all beer and skittles,” he said.
In Singapore, Freedman trained 456 winners, including 36 at Group level, in both Singapore and Malaysia. He dead-heated with Laurie Laxon in the 2012 trainers’ premiership.
By 2016, the triplets were advancing into secondary school. Family had always come first and they returned home for just a few months before Freedman accepted an invitation to train in Hong Kong. The kids went to boarding school.
It had all happened in a rush, and it would end in a similar way.
What a win by Marhoona in the G1 TAB Golden Slipper, proving dreams can come true!
— SKY Racing (@SkyRacingAU) March 22, 2025
She wins for @MFreedmanRacing and @LaneDamian! 👏@EmiratesPark | @aus_turf_club pic.twitter.com/EAq92UCjBf
“The walking machine incident was part of it, no doubt. But the whole thing seemed rushed and I really didn’t enjoy the lifestyle from the get-go,” he said.
“Besides, I was missing the kids a lot.”
He and Richard then teamed up in Sydney. Despite the phenomenal success of the Freedman brothers, it had at times been chaotic chemistry.
Anthony and Lee had mostly grunted at each other but grunting was a language they understood. Michael and Lee had always gotten along, hence a few beers and a handshake led to this most recent decision to again team up on the Gold Coast, a satellite operation to Michael’s squad of 55 at Randwick.
But Michael and Richard? Would that work?
“We both went in with best intentions but quite different philosophies. There were enough disagreements where something had to give. I look back and it actually makes sense that he now trains with his son Will. It’s probably how it should have been all along,” Freedman said.
The Freedmans have a knack for resurgence and reconnection.
Introducing The Good Oil - Melbourne Form Previews, Price Assessments and Mounting Yard Mail
Lee Freedman won four Slippers on the trot in the mid-1990s. The FBI - Freedman Brothers Incorporated – would disband but that streak was a collective effort.
Stay Inside won for Richard and Michael in 2021 – days before they split – and Michael won it in his own right with Marhoona this year.
Michael says the graininess of the footage of Mahogany, Super Impose, Naturalism, Sauna and all the others from that era, when he was at Melbourne Grammar and Lee fast-tracked into training with the death of their father, makes those times seem a little ancient.
Bren O’Brien
Almost 40 years on, he now finds himself in charge, Lee as the assistant.
“I guess it’s the way life goes. Lee still loves what he does but has nothing left to prove. He’s won all there is to win and still loves training the horses without the headaches,” he said.
“We did have a chat about the dynamic of how it would work out. I will send the right sort of horses up there, ones a step below metro Sydney. I’ll set certain structures in place but who am I to interfere with how Lee trains them? At the end of the day, we all train very similarly.
“I learned a hell of a lot from Lee but I’d like to think we all learned a fair bit from Dad as well.
“I look back fondly on those days up at Leonard Crescent and what we’ve all managed to achieve. We all know Dad would be proud.”
POSTSCRIPT: Max is about to finish a degree in veterinary science, Sophie graduated in sports science and works for the Gold Coast Suns and Jessica is involved in interior design.
Freedman says it would have been nice if at least one followed in his footsteps “but I’m also over the moon that they haven’t.”
