Pinn had an extended winter stint in Victoria two years ago and has grown as a rider since, clearly establishing himself as one of our best with the all-important temperament for black-type racing.
But with Sydney being one of the world’s most lucrative racing jurisdictions, Pinn says he wants to at least dip his toe in the water.
“I think the time is right, with winter coming up at home and all the major races for the season done,” Pinn told the Herald.
“I came over last week and rode at the trials on Thursday and have been riding some work for Chris.
“Obviously I’d love to get on some of his horses race-day but essentially I will be a freelance rider.
“Riding in town [metropolitan meetings] is the main aim but I won’t be scared to travel around the state to establish myself so am open to offers.”
Just how established Pinn gets will be keenly watched by New Zealand trainers and punters, who will be hoping he returns in the new season.
“Anything is possible at the moment but the idea is to head back home in the spring,” he says.
“But if things go really well then who knows. There is a lot of money and a lot of racing in New South Wales so I will see how I fit in.
“I have some really smart horses I could be riding back home in the spring though, horses like El Vencedor which are hard to get on anywhere so yes I am thinking I will come back but as we all know things can change.”
Pinn’s partner Tayla Mitchell, a one-time apprentice premiership winner, will join him in Sydney soon while serving a suspension but her winter plans are not as concrete.
Leading jockeys leaving New Zealand for the winter is nothing new as most of the biggest names take some sort of winter holiday, some simply riding less as stakes decrease. Jumps racing means less options and trainers use apprentice allowances more on the often heavy tracks.
And some of the most senior riders simply don’t want to burn out riding 12 months of the year so use winter as their freshen up.
While New Zealand will never be able to compete with the stakes and scale of Australian racing there has never been a more profitable time to be a jockey here, with 28 domestic jockeys each having ridden the winners of over $1m in stakes so far this season.
Remarkably three visiting Australian-based jockeys have also ridden more than $1m worth of winners in New Zealand this season, with Blake Shinn’s mounts winning $2.7m in stakes even though he had only 20 rides here.
Ex-pats Rory Hutchings and Mick Dee have also bagged over $1m in stakes here, Dee winning $1,569,300 for connections in just nine rides.
Michael Guerin wrote his first nationally published racing articles while still in school and started writing about horse racing and the gambling industry for the Herald as a 20-year-old in 1990. He became the Herald‘s Racing Editor in 1995 and covers the world’s biggest horse racing carnivals.