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Top jockey Opie Bosson is hoping he pulled the right rein in his bid to cracking it for a second Emirates Singapore Derby win this Sunday.

Given first refusal for either Gingerbread Man or Red Beard – both prepared by trainer Bruce Marsh - in the Group 1 event over 2000 metres, Bosson elected for the latter when most thought he would have stuck with the better-credentialed Gingerbread Man.

Back in 2010, the heavyweight rider was not faced with any choice to make when he got onto Race Ahead in the Derby. Marsh had then specially flown him in from New Zealand for that one ride – and it proved a perfect hit.

Two years on, he recombines with Marsh in the $1.15 million event, but the dynamics have changed slightly. Following a recent upgrade of the status of his licence (originally rode exclusively for Marsh and fellow Kiwi Mark Walker) Bosson now rides freelance in Singapore and has ridden both Gingerbread Man and Red Beard this campaign.

Having partnered former juvenile and three-year-old champion Gingerbread Man at all his runs since New Year's Day, including his triumph in the first Leg of the Singapore Four-Year-Old Challenge, the Group 2 Stewards' Cup (1400m) on June 3 versus only two rides for one win on Red Beard, Bosson was widely expected to pick the horse he knows best in the third Leg, the Derby.

But the decision was not so clear-cut for Bosson, who after careful deliberation, did a switcheroo for Red Beard, a last-start winner when carrying 51.5kg – a weight he could not make anyway - under leading jockey Joao Moreira in a 1400m Handicap race on June 24.

Racing is replete with stories of jockeys who made the wrong call when choosing rides, but Bosson was a picture of confidence after jumping off Red Beard in a barrier trial on Tuesday morning. Though he feels both horses are in with a chance, it is clear that the upsides are leaning more towards Red Beard in his mind.

“I've always liked the horse (Red Beard) and did work on him a fair bit,” said Bosson. “It was a hard decision to make as they're both two very good horses.

“But I did feel Gingerbread Man was not quite at his best at his last run (third to Ato in Patron's Bowl over 1600m on June 24). He has however come on very well since that run and will be presented in tip-top shape on Sunday.

“Red Beard did not have an ideal preparation, going straight from 1400m to 2000m, but we had no choice as he had been away for so long and the Derby was always his main target.

“He's had a nice run under the circumstances and his last win showed he was peaking at the right time. The 1600m would probably have suited him better, but he's pretty classy and he should have enough class to do it.

“He had a bit of a puff in his trial this morning. He needed it and that should bring him on nicely for Sunday.”

Bosson said the son of Japan Cup (2400m) winner Zenna Rob Roy will find little trouble seeing out the 2000m, but said Gingerbread Man would also get the trip.

“He's (Gingerbread Man) run second over the trip before and he will be right there,” said Bosson who counts only one success (Stewards' Cup) with the son of Shamardal from seven rides.

“He should be in the first three, but a lot will depend on the barrier draw. A good draw will make things a lot easier for both horses.”

With Bosson jumping onto Red Beard, Marsh has retained the services of a jockey he does not use very often for the ride on Gingerbread Man – local hoop Saimee Jumaat.

“Saimee may not get as much support these days, but he's been around long enough and is a nine-time champion jockey,” said Marsh, himself a former jockey who counts a Melbourne Cup win aboard Silver Knight in 1971 as his biggest claim to fame. “He's a class rider and I had no hesitation in putting him on.

“Opie chose Red Beard on his own, but that's his choice. As far as I'm concerned, both horses are in terrific order, but the barrier draw will play the biggest part.

“Remember Better Than Ever who drew the outside and led last year to finish second. If he had not drawn so badly, he would have won.

“Ideally, I would like my three horses (he also saddles Hammer Down who will be ridden by Oscar Chavez) to draw 1-2-3 and finish 1-2-3 but that would be a dream, wouldn't it?”

Marsh kept a watchful eye on Red Beard as he trialled on Tuesday, galloping on for a close-up fourth to Jamal Malik.

“I'm very happy with that run. Opie had to give him a bit of a dig in the last bit, but that is his trademark as he tends to loaf when he hits the front,” said Marsh.

“He needed a proper gallop and that will clean him up nice for the Derby. He's had a solid background work and we'll now just keep him ticking over.

Marsh will send Gingerbread Man for a gallop on grass on Wednesday morning while Hammer Down, who did not back up on his encouraging third to Gingerbread Man in the Stewards' Cup with a disappointing eighth to Ato in the Patron's Bowl, will gallop on Track 4 (Polytrack).

“He (Hammer Down) gets too keen on grass. He gallops too hard,” said Marsh.

“I prefer to put him on Track 4. He's had lots of gallops and is very fit anyway.

“As for Gingerbread Man, he pulled up good after his last run and has come on very well since. He will run a bold race, too.”