TWO-time Cheltenham Festival-winning jockey Tom O’Brien established himself as a horse racing great up until his retirement in 2023.

The world was rocked into mourning when he passed away on November 11, 2026, at the age of 39, . But he is survived by his wife, Hayley, and their children.

Jockey Tom O'Brien wearing a green and blue star-patterned racing silks and matching helmet.
Jockey Tom O’Brien was a horse-riding great until his retirement in 2023 Source: PA:Press Association
Chepstow Races
Keep reading to find out about his family life Source: Getty Images – Getty

As a rider, achieved a mightily impressive five Grade One successes, the first of which dated back to 2007.

That campaign was his breakthrough season in the sport, as he picked up 105 winners in 2006/07 and was crowned champion conditional with the help of trainers Peter Bowen and Philip Hobbs.

Tom was the nephew of training legend Aidan O’Brien, with his dad, Jim, still working with Aidan’s son Joseph at his base in Kilkenny.

O’Brien picked up more than 1,000 wins in his career, notably winning the Welsh Grand National on two separate occasions.

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Tom O’Brien picked up five Grade One successes across his career Source: Shutterstock

His 2009 against-the-odds victory at Chepstow was made into an award-winning 2015 documentary titled Dark Horse: The Incredible True Story of Dream Alliance, which was later adapted into a 2021 feature film.

Later in his career, O’Brien saddled up on Thyme Hill and was able to secure the 2021 Liverpool Hurdle and 2022 Kauto Star Novices’ Chase.

Away from the racecourse, the Wexford-born jockey married his wife, Hayley, but who is she, and how many children did the couple have?

Who is jockey Tom O’Brien’s wife?

Tom O’Brien and his wife, Hayley, enjoyed a life largely centred around his racing career.

A smiling man in a purple jacket, a blonde woman, and a young child in a baby carrier together outdoors.
Tom had two children with his wife Hayley – Toby and Archie

That was until the jockey’s retirement in April 2023, where O’Brien transitioned into a role as a member of the British Horseracing Authority’s (BHA) stewarding team.

This allowed him to stay connected with horse racing, whilst also finding time to enjoy his family life too.

Together, Tom and Hayley had two young sons, Toby and Archie.

Johnson White, training partner to Philip Hobbs, told the Nick Luck Podcast : “You couldn’t get a harder worker, nicer family man.

“I messaged Richard Johnson this morning and he messaged back saying ‘life is so cruel’.

“He leaves a lovely wife, two boys and a loving family who were there with him to the end.