Coach reveals how jockey Dean Holland was chasing his racing dream two hours before tragic death

It’s been revealed that star jockey Dean Holland was in the process of applying for his dream racing gig in Hong Kong just two hours before his tragic death in a race fall.

The two-time Group 1-winning jockey, 34, leaves behind wife Lucy and four children aged under five – Harley, Luca, Frankie and Lily – and the tight-knit racing community is in shock for the hugely popular rider.

Heartbreakingly, his long-time coach, ex-jockey James Winks, revealed that the in-form Holland was keen to ply his trade in Hong Kong because of how happy and settled he was with his young family.

Before his tragic death, Holland was in brilliant form. Just weeks prior he won his second Group 1 race on In Secret in the Newmarket, and had already clocked up 82 winners in Victoria this season.

After years of slogging it out across country and metropolitan courses all over Victoria and South Australia, accumulating more than 1000 wins, Holland was finally getting the plaudits he deserved.

Dean Holland won his second Group 1 on March 11, and such was his brilliant form before his tragic death, his coach suggested he should apply to race in Hong Kong

The South Australian native celebrates after winning the 2015 Adelaide Cup, one of the biggest victories of his career

Holland died in a race incident on Monday, leaving behind wife Lucy and four children under the age of five (two pictured): Harley, Luca, Frankie and Lily

Ex-jockey James Winks, who coached Holland and a number of other riders, revealed he was helping Holland with his application to race in Hong Kong just two hours before his death

And Winks implored him to push himself in the glamorous, fast-paced and rich racing world of Hong Kong, with the pair collaborating on his application to the racing authorities over there just two hours before his tragic death.

‘He (Holland) wanted me to read his resume yesterday so we were back and forth on the text messages so I ended up ringing him,’ Winks told Racenet.

‘He said, ‘I’m settled with my beautiful family now so it (riding in Hong Kong) is something that I wanted to do’. Two hours later, he lost his life.’

Winks has won a Group 1 race in Sha Tin himself – he knew Holland was ready. 

Instead, he is now left wondering what might have been. 

The jockey mentor has a very close-knit book of clients, who are now all completely devastated at the loss of their mate.

With racing in Victoria quite rightly called off on ANZAC Day in the wake of the tragedy, a number of top hoops caught up for a beer to remember Holland and process the loss together. 

A number of jockeys coached by Winks, including (L-R) Dylan Dean, Zac Spain, Jordan Childs, Tom Conlan, Ash Thompson and Jordan Dean gathered at a Melbourne pub to remember their great mate on Tuesday

‘We’re all meeting today just to have a beer for him to get around each other. We all formed a team bond just by doing things like training together and they’re all shattered,’ said Winks.

‘It makes it even harder when you start thinking about his wife and kids. It’s just devastating when you know that they’re not going to have a father.

‘My wife is distraught and my little fella loves racing and he asked me this morning whether Dean was going to come back. It really hits home.’ 

The 34-year-old was riding the Tony McEvoy gelding Headingley on Monday in Donald, north-west Victoria, when he was involved in a fall described by onlookers as ‘sickening’. 

Tragically, his parents – who are also heavily involved in racing – witnessed it live on television.

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

Holland was airlifted to hospital in a critical condition after a sickening race fall in country Victoria, and, tragically, could not be saved

Alana Kelly and her mount Time to Rumble were then also brought down, with the full force and weight of both horses appearing to land on Holland, who remained prone on the turf.

Miraculously, both mounts avoided injury and ran away from the scene, while Kelly was able to walk back to the scales.

Horse racing is literally a case of life or death for jockeys based on things that happened in the blink of an eye.

Michael Walker, who was forced into retirement recently after a sickening head injury suffered in a trial last year, summed it up best.

‘It’s such a hard job. You try and tell me how many professional jobs you have in this world that an ambulance follows you around,’ he told the Sydney 

‘When things are going well and you’re winning those big races, that’s what we live for.

‘But it can end your life if things go wrong.’

The racing world sent messages of support to Holland’s (second from right) wife Lucy (right) following his death 

Holland, who won the 2021 Geelong Cup aboard Tralee Rose, recently posted a photo of his four children, Harley, Luca, Frankie and Lily, at Geelong Racecourse in front of a sign immortalising his win

Amidst what would no doubt be overwhelming grief, Holland’s family, who are highly-respected members of the racing community in South Australia, said they too were thinking of all the other riders who shared a jockeys room with their son, brother and partner.  

‘We are aware of thousands who are sharing our pain as we come to the reality we have lost a once-in-a-lifetime person, a much loved partner, an amazing father of four beautiful young children in Harley, Luca, Frankie and Lily, as well as a special brother and a wonderful son,’ the family said in a statement.

‘The outpouring of love for Dean and the care and support for us is helping us deal with our loss.

‘We are thinking of Dean’s colleagues in the jockeys’ room as well as all in our industry that he loved so much.’

Prominent racing identity Tony Ottobre has started a fundraiser in the wake of the tragedy, and it has already raised more than $865,000. 

To donate to the GoFundMe for Holland’s wife Lucy and their four children, click here.