Trainer mate of jockey Dean Holland who died in horror fall reveals their last conversation

Horse trainer Jon O’Connor has revealed he’s been left so shattered by the tragic death of his great friend Dean Holland in a race fall that the loss makes him ‘almost want to walk away from racing’.

Holland, 34, died in a sickening incident in country Victoria on Monday, leaving behind his wife and four children under the age of five.

He was riding Tony McEvoy gelding Headingley in the first race at Donald, 280km north-west of Melbourne, when he was involved in a fall described by onlookers as ‘sickening’.

Holland was thrown to the turf when the three-year-old gelding moved sharply to the inside rail before falling as the field turned for home at the top of the straight.

Dean Holland (pictured after winning the Group 1 Newmarket Handicap on March 11 at Flemington) died on Monday in a sickening race fall in country Victoria

Dean Holland (pictured after winning the Group 1 Newmarket Handicap on March 11 at Flemington) died on Monday in a sickening race fall in country Victoria

South Australian trainer Jon O'Connor (pictured, centre) knew Holland since he joined his team as a 15-year-old apprentice and even rode with the jockey's father

South Australian trainer Jon O’Connor (pictured, centre) knew Holland since he joined his team as a 15-year-old apprentice and even rode with the jockey’s father

Holland is unseen under the first downed horse during the deadly fall, which also brought down jockey Alana Kelly (pictured centre in pink and blue silks)

Holland is unseen under the first downed horse during the deadly fall, which also brought down jockey Alana Kelly (pictured centre in pink and blue silks)

He was treated on-course by medical personnel, before being airlifted to a Melbourne hospital in a critical condition. Victoria Police confirmed his death just after 4pm.

O’Connor first met Holland when the hoop joined him as an apprentice aged just 15 and the pair stayed in touch.

‘They become like family, your apprentices, when they’ve been with you that long,’ O’Connor told Racenet.

‘His dad and I rode together … We all know the risks but the impact when you’ve got that history with them… it’s just that feeling of disbelief.

‘I don’t like to say it, but it makes you hate racing sometimes.

‘For all the sacrifices people make, and he’s made the ultimate sacrifice, it makes you almost want to walk away from racing.’

The pair last met on Saturday ahead of the City of Adelaide Handicap and O’Connor revealed he asked the rider about his huge workload.

The 34-year-old leaves behind his wife Lucy and their four young children (two of whom are pictured with the couple)

The 34-year-old leaves behind his wife Lucy and their four young children (two of whom are pictured with the couple)

Holland (pictured after a race win at Flemington in 2020) became 'like family' to O'Connor and the pair kept in touch

Holland (pictured after a race win at Flemington in 2020) became ‘like family’ to O’Connor and the pair kept in touch

‘I was having a chat to Deano before the race … I mentioned how many meetings he was riding at and his workload, and he said, “I’ve got an ambition to ride 100 winners for the first time this season. I just want to crack the 100 and then I’ll have a bit of a rest and be a bit more selective” instead of riding just about every day like he was,’ O’Connor recalled.

‘That was the last conversation we really had and it’s just very hard to get your head around.’

The veteran jockey rode 1080 winners – accumulating $32.4million in prizemoney for connections – during a superb career, which includes Group 1 wins in the Newmarket Handicap in March and Australasian Oaks in Adelaide, where he cut his teeth as a rider.

Ironically, that Newmarket win on In Secret only came because superstar rider Jamie Kah was in hospital (where she remains) with a very serious head injury – and he said at the time he didn’t want to ‘yahoo’ about the win because she should have been riding it.

The meeting was swiftly abandoned on Monday, with the racing world in complete shock and devastation at the tragic death.

A younger Holland salutes the crowd after winning at Flemington in 2009. He made more than $32million in prizemoney during his outstanding career

A younger Holland salutes the crowd after winning at Flemington in 2009. He made more than $32million in prizemoney during his outstanding career

Trainer Peter Moody wrote a tribute of his own: ‘Vale Dean Holland. Thoughts and prayers to Lucy and his beautiful young family Way too soon, RIP young man.’

Pundit Samuel Hyland also spoke of his sadness that the popular jockey had died.

‘Such sad news to hear that Dean Holland has passed away. Deano was a fantastic jockey, hard worker & such a great bloke, condolences to his lovely family, it is just so sad,’ he said.

One punter called it the ‘most sickening fall I have seen’, with another writing it was ‘so sad to see this happening far too often’ – after a spate of very serious race falls involving superstar riders Jamie Kah and Craig Williams, as well as top hoops Ethan Brown and Teo Nugent in the last few months.

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