Wheeler rode his first winner at 16 years of age when booting home the Bjorn Baker-trained Airstrike at Goulburn in 2021.
He had ridden a host of winners across country New South Wales, before opting to take some time off away from racing last year.
Highlighted in a powerful piece with Racenet’s Trenton Akers in March, Wheeler speaks openly about some cross-roads he had reached early into his career and the maturity shown to revive his career in South East Queensland.
A major catalyst behind this resurgence was his new boss, Eagle Farm trainer Chris Anderson.
“He is one of the best bosses you could ask for,” Wheeler said.
“I speak to him about all things inside and outside of work. He is so understanding. Not many people get a boss like that. He is a very good bloke.
“He has been able to support me a lot with the horses he has and hopefully we can keep building that.
“He wants what is best for you and he gets the best out of you.”
The bond between master and apprentice has certainly been replicated on the racetrack, with the pair combining for 11 winners in 47 rides.
“(Anderson) has some nice young horses and he is still getting better each season as a trainer,” Wheeler said.
“Hopefully when those horses go to town I can go too and keep building with each other.”
Just like any star team or athlete, the crew behind the scenes is just as, if not more, important than the athlete themselves.
In addition to Anderson, Wheeler’s father, Dan, and manager, Adrian Gray, are essential points of call.
“The sort of people behind me, my Pop, my dad, Adrian, Zac Purton, all these people behind the scenes help massively,” Wheeler said.
“My manager Adrian Gray does a great job. My godfather Zac Purton I also speak to regularly.
“I can call Dad whenever I want and talk to him about anything I want, which helps so much. Everything I know, he knows.”
Gray knew Bailey and his father from their Gold Coast days and was one of many in the industry who could see the clear potential.
“I (began managing him) basically a week after he commenced riding races in Queensland, but I’d been on the blower to his boss Chris Anderson about taking him on the second I heard he was moving up,” Gray said.
“I saw him ride one of his first winners live on TV—Omar for Patrick Cleave—and couldn’t get over how well he could hit for a 4kg (claiming apprentice).”
Although Gray wasn’t managing him at the time, he and Wheeler have spoken of Wheeler’s time away from racing and the life lessons learnt.
“H’s come out the other side better for the experience and a more mature, well-rounded person and rider,” Gray said.
“His riding is now a testament to that and sets him ahead of the rest.”
This experience and Wheeler’s ruthlessness for success is a scary proposition for any competition.
Gray describes Wheeler as “a dog with a bone all day, every day” and how his appetite for success grows with each milestone.
“A couple of times I have basically had to say ‘just chill – I will sort it out’,” Gray said.
“(His desire) will get him to where he wants to be.”