Shepherd’s delight at Royal Ascot after breakthrough success on Isle of Jura

On a sunny afternoon at Lingfield Park last month, having just won the Lingfield Derby Trial on Ambiente Friendly, Callum Shepherd was looking forward to his first ride in the Epsom Classic and all seemed right in his world. Six weeks later, he was looking to the future again on Saturday after winning the Hardwicke Stakes on Isle Of Jura, but the difficult back-story of the month-and-a-half in between was clear from Shepherd’s heartfelt celebration as he crossed the line.

He has been through the mill since what felt like a breakthrough success on Ambiente Friendly. He did nothing wrong on James Fanshawe’s colt. Quite the opposite: he did everything right on an often tricky and headstrong horse. But he soon learned he had been “jocked off” for Epsom by the owners, Bill and Tim Gredley. As Ambiente Friendly and Rab Havlin, his new rider, went to post at Epsom on 1 June, Shepherd was back at Lingfield, for five rides on the all-weather.

Related: Royal Ascot day five: Khaadem wins Queen Elizabeth II Jubilee Stakes again – as it happened

A hugely promising start to the season seemed to be leaking into the sand. The winners were drying up, but one horse did not let him down. Two days after finding out that he had lost the ride on Ambiente Friendly, Shepherd rode Isle Of Jura to a narrow win in a Listed race at Goodwood, which booked his place in the field for the Hardwicke. The four-year-old was a 16-1 shot in Saturday’s much stronger field, he emerged as an emphatic winner.

“Six weeks ago, I thought I’d found my diamond,” Shepherd said. “That wasn’t to be, but [Isle Of Jura] has certainly blossomed into one.

“We had a great winter and I’d ridden plenty of winners, it was all going pretty smoothly, but that’s sport, it won’t all go your way for long. I’m just so fortunate to have this horse to continue to bring me to the big occasion. We’ve not made too many mistakes yet and hopefully it can stay that way.

“He’s just kept improving, he’s never let us down and he’s felt better with every start. He’s become very straightforward and he’s got a real desire to win as well. He was rusty at Goodwood but you still saw that innate desire to pass the post in front, which is so important.”

Isle Of Jura was a first Royal Ascot winner for Shepherd and George Scott, his trainer, and the obvious target for the winner is the King George VI & Queen Elizabeth Stakes, over the same course and distance, at the end of July.

“All roads lead to the King George, 100%,” Scott said. “Callum gave him a perfect ride, he sat nice and tight to a slow pace and was in pole position to kick early and put the race to bed.”

Khaadem, the 80-1 winner of the Queen Elizabeth II Jubilee Stakes 12 months ago, was 66 points shorter in the betting this time around but the outcome was the same, albeit with  Oisin Murphy taking over from Jamie Spencer, last year’s winning rider.

Aidan O’Brien and Ryan Moore, meanwhile, took their tally for the week to six wins when Bedtime Story landed the Chesham Stakes with such an exhilarating performance that she replaced her stable companion Fairy Godmother, the winner of Friday’s Albany Stakes, as the favourite for next year’s 1,000 Guineas.

Fairy Godmother came from a seemingly impossible position to claim the spoils in the final strides, but there was no similar anxiety for backers of Bedtime Story, who was close to the pace from the off and then blitzed into an unassailable lead well over a furlong out on the way to a nine-and-a-half length success.

It was an astonishing winning margin for a seven-furlong contest, and challenged the 11-length gap between Frankel – Bedtime Story’s sire – and his field in the Queen Anne Stakes here in 2012.

“This was the first time she was asked to stretch,” O’Brien said. “Ryan said he couldn’t believe it, everyone fell away, she just took off. He didn’t even give her a slap down the shoulder.

“We thought she was probably a Group One filly, but we hadn’t looked. Thinking is one thing and seeing is another, so everyone saw it together today.”