Queensland-based Dolan rode the 80/1 outsider to victory in a photo finish at Flemington Racecourse in his first ride in “the race that stops the nation”.
Having long juggled singing aspirations with a career on the turf, the 28-year-old is accustomed to being in the spotlight.
He made it through several rounds of Australia’s version of the hit singing show in 2022, and fittingly sung “Horses” by local performer Daryl Braithwaite as part of the entertainment at the Cox Plate, a prestigious race in Melbourne.
Much like his singing, the County Kildare native had his moments in racing without a career-defining breakthrough since moving to Australia eight years ago.
That all changed on a sun-drenched Tuesday at Flemington when he produced a run that had champion jockeys singing his praises among the bumper crowd of 91,000.
Knight’s Choice was lengths adrift of the front-runners in the final straight but accelerated hard at the 200m mark, snatched the lead with 50 metres left and held off Japanese stayer Warp Speed by a nose.
“I think I’ll be singing for the rest of my life after that,” said Dolan.
“I feel like I’m going to wake up any minute. Can you pinch me?”
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Another Irish singer, Ronan Keating, was part of the entertainment at Flemington and the former Boyzone frontman shared a post-race embrace with the winning jockey.
“I could have easily given up riding to do the music, but I just loved it too much,” added Dolan.
“You work so hard not only as a jockey, but just in the racing industry – you get up early hours, long days, long nights, and not a lot of breaks.
“Once I started doing a little bit of music, it was a nice change. I’d just been grafting for 10 years before that.
“At one stage, I was struggling to get a few rides, and I was thinking, ‘Gee, I might just do the music on the side’. And then I just missed riding winners, I missed the camaraderie of the jockeys in the room.”
Knight’s Choice was the longest-odds winner of the Cup since 100-1 shot Prince of Penzance made Michelle Payne the first female jockey to win the race in 2015.
While few punters cheered the result, Knight’s Choice delivered co-trainer Sheila Laxon her second Melbourne Cup trophy, 23 years after she became the first woman to prepare a Cup winner in the 2001 race with Ethereal.