RARE CHANCE: Grafton jockey Olivia Pickering will become the first apprentice to ride in the Grafton Cup this decade when she gets a leg up on Jack Strikes Back for today's feature race. BELOW: Pickering guiding Jack Strikes Back to a win.
RARE CHANCE: Grafton jockey Olivia Pickering will become the first apprentice to ride in the Grafton Cup this decade when she gets a leg up on Jack Strikes Back for today's feature race. BELOW: Pickering guiding Jack Strikes Back to a win. Matthew Elkerton

Master and the apprentice chase the golden chalice

GRAFTON CUP: It will be a case of the bold and the young in the $160,000 G McMullan Contracting Grafton Cup (2350m) today when the experienced Neville Stewart teams with fiesty apprentice Olivia Pickering on local hopeful Jack Strikes Back.

The honest seven-year-old gelding, owned by Billy Sharpe, has been a handy galloper since joining Stewart's Grafton stables and has pocketed more than $130,000 in prizemoney across his 66 starts, but the Grafton Cup is by far the toughest field he has come up against.

He put in a valiant run for the stable in the Westlawn Finance Grafton Cup Prelude when he led the field for most of the 2300m journey before getting pipped in the final stages to run fourth, a length and a half behind fellow Grafton Cup starter Chillin With Dylan.

Pickering, who does every bit of the cantankerous gelding's work, was on board for the Prelude last Thursday, and said the run had primed the gelding for another gallant showing in today's feature race.

"That run in the Prelude was an enormous effort from him,” Pickering said. "He led for most of the way and the others just nipped him at the post, but it has set him up perfectly.”

It will be a ground-breaking moment for the Grafton Cup, with Pickering the first apprentice to ride in the listed feature this side of the decade.

If she wins, that period more than triples.

But for the girl who crossed the ditch from New Zealand in search of success, it is just another stepping stone on her path to a long-term career in the saddle. A stepping stone she never thought she would reach.

Neville Stewart looks at the Grafton Cup - as he prepares to saddle up Jack Strikes Back.
Neville Stewart looks at the Grafton Cup - as he prepares to saddle up Jack Strikes Back. Adam Hourigan

"Not in a million years did I think I would get a start in the Grafton Cup, I am so excited about the opportunity, there is no room for nerves,” she said.

"Apprentices can't claim in the Cup, so there is no reason to put me on. They honestly could have gone with any jockey they wanted to, there are so many in town already riding big races, but they chose to go with little old Olivia Pickering.”

Stewart, who won the Grafton Cup back in 1993, put it quite simply when he explained the reasoning behind sticking with Pickering.

"She knows the horse inside out, she does all of his work, and she has had success on him in the past,” he said.

"I did think about the fact she can't claim in the Cup, but it is not about that. It is about her connection with the horse.”

It is a connection that has helped the seven-year-old reach the heights that he has.

A cantankerous galloper, Jack Strikes Back has been known around the traps as tough to deal with in trackwork, but not for Pickering.

There is something in the young apprentice that the horse has taken a fondness to and even she can't put her finger on it.

"He can be a little bit naughty, especially in his trackwork, he doesn't always like to do what he is told,” she said. "But for me it is different. We just have this connection, we have a little click going together.

"I don't know what it is, I think it is just one of those random things that happen between a jockey and a horse. Some horses you work well with, others you tend to avoid.”

While Jack Strikes Back will be making a big step up in grade for the Grafton Cup, Pickering said she had every confidence he would put his best foot forward when the gates open.

"It is a bit of a tricky race, and we have drawn wide in barrier 16, which doesn't always help,” she said. "He likes to be up on the pace and getting running, but I am not too worried about that. He has a lot of speed out of the gates and that should help him get out the front and lead the race.”

Jack Strikes Back will likely be joined up on the speed by Chris Waller-trained Montauk, who will also have to overcome a wide barrier draw in 20.

If Stewart knows anything, it's that he can't do much more than he has with the gelding.

"He is fit and firing, he is in the best shape he is ever going to be,” Stewart said. "Now it is just about the luck of the Cup.”



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