Sherwood has eyes on matching brother and the legendary Dessie

THE evocative photograph of a mud-splattered Desert Orchid winning one of the most famous Cheltenham Gold Cups in history will always be synonymous with the Sherwood family.

Simon Sherwood riding to victory in the Cheltenham Gold Cup on Desert Orchid

On saturated ground which almost led to jump racing’s most celebrated prize being abandoned, the great grey – owned in North Yorkshire by Richard Burridge and known to all as ‘Dessie’ – clears the last fence under Simon Sherwood before setting off in pursuit of the mudlark Yahoo, who appeared destined to become the ultimate party-pooper.

Willed on by a wave of public adulation which transcended all sport, the denouement to the 1989 Gold Cup is encapsulated by Sir Peter O’Sullevan’s spine-tingling commentary: “There’s a tremendous cheer from the crowd as Desert Orchid’s going to win it... Dessie’s done it.”

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Television pictures showed trilby hats – and betting slips – being thrown in the air amid the delirium.

Yet, more than a quarter-of-a-century later, it is the winning jockey’s older brother, Oliver, who holds the key to the outcome of Friday’s Betfred Cheltenham Cup when he saddles the well-regarded Many Clouds.

Owned by two-time Grand National winner Trevor Hemmings, one of the great patrons of National Hunt racing, Many Clouds won a three-runner novice chase at Wetherby in December, 2013 before showing his class to land last November’s Hennessy Gold Cup at Newbury.

It is not just the colour – Many Cloud’s coat is brown – which differentiates these two equine warriors. The almost white Desert Orchid, who had national treasure status by now, hated the mud. Guts carried him home in 1989, and he was never seen at his best at left-handed tracks like Cheltenham. He was, however, the undisputed king of Kempton, Sandown at Ascot and versatile in trip – this was a horse quick enough to win Group One races over two miles and an Irish National in 1990 over nearly double the distance.

In contrast, the Many Clouds team would like to see a deluge in the Cotswolds prior to their own day of destiny – especially after the horse, an out and out stayer, showed a likeness for Cheltenham’s testing fences when winning the track’s own Gold Cup trial at the end of January.

Victory would mark a remarkable renaissance for Oliver Sherwood, who is seeking his first Festival win since Coulton in 1995 – only now is he emerging from a slump which came close to ending his career as a trainer.

“He hasn’t missed a day. He hasn’t missed a beat,” Lambourn-based Sherwood told The Yorkshire Post when asked about the well-being of Many Clouds.

“He knows he is King Kong. He’s the perfect three-mile chaser. We would like a little bit of rain, but there’s no point crying over what no-one down here can control but Him upstairs.

“We ran Many Clouds in the trial around Cheltenham to get experience. I think he has improved again – but he needs to if he is to tick all the boxes. The other thing going for him is that many of his rivals are seasoned campaigners who may have flattened out. He’s still an improving horse – what you don’t know is how much further he is going to improve.

“The one race every trainer or jockey in National Hunt racing wants to win is the Cheltenham Gold Cup. It’s the Holy Grail of jump racing, the creme de la creme, the gold medal race. It was very special when Simon won the Gold Cup, but it would have been better if he was riding for me! I wouldn’t say his win was a motivation; this is what we all strive for. It’s the ultimate. I saddled Arctic Call, who was pulled up in 1991, but it’s great to be going back to Cheltenham with a good horse with a live chance.”

Sherwood’s excitement is shared by younger brother Simon, who is now clerk of the course at Ludlow.

He says they grew up aware of their father’s sage advice ‘never go to the grave wishing you had when you hadn’t’ and his role model was Yorkshire’s very own show-jumping legend Harvey Smith.

When riding his pony Simon in a jump-off for the first time, the then eight-year-old recalled the first thought that passed through his head: “I am Harvey Smith and England depends on me.”

It was a positive mindset which was to serve the younger Sherwood well as he graduated through the riding ranks and point-to-point sphere through to a career which culminated with his career-defining association with the David Elsworth-trained Desert Orchid – the Muhammad Ali of steeplechasing.

While today’s top-class jumpers are raced sparingly, Sherwood rode the nation’s favourite racehorse on 10 occasions from December, 1986 until April, 1989 when Desert Orchid, normally the bravest of jumpers, fell at Aintree just weeks after his Cheltenham heroics. It was a race too many.

It was the only time Sherwood was defeated on the horse – and it was one of his last rides before he retired from the saddle.

“Oliver and I were pretty close as brothers, but always competitive,” said Sherwood whose son Jack is an up-and-coming rider attached to the yard of champion trainer Paul Nicholls. “Oliver was always keen to impress upon me his existence and the fact he was three months older.

“Once I got to 13 or 14, I was going to be small enough to be a jockey and I am very proud to have ridden 345 winners under rules. To win a Gold Cup on a horse like Desert Orchid, they are the days you dream about.

“This is a horse who was more than quick enough to win a Queen Mother Champion Chase, but he just wasn’t suited by Cheltenham. It was left-handed and an undulating track. If the Gold Cup had been run anywhere else, he would have racked up four or five wins – he was that good.

“On the day itself, there were lots of stewards inspecting the track and there were fire engines pumping the water off the track.

“I think he was always going to run – the owner, Richard Burridge, was huffing and puffing but David Elsworth was determined.

“He received a huge cheer just cantering to the start and there were plenty of casualties in the race. It was fortunate that he was still good enough to beat Yahoo while running 20lb below the best because of the track and heavy ground.

“Going to the second last, I thought we were beat – but then he began to rally. Halfway up the run-in, I thought we had the race. Guts – that is what got Dessie home. Guts. I won the ultimate race on the ultimate horse.

“Desert Orchid probably had a bit more class and versatility than Many Clouds has shown, but my brother’s horse is a lovely, honest animal who gallops all day. I hope he wins.”

Simon Sherwood’s race-by-race record on Desert Orchid

THE heart-stopping Cheltenham Gold Cup win of Desert Orchid was the culmination of a remarkable relationship between the gallant grey and his jockey, Simon Sherwood...

December, 1986: Won Kempton’s King George VI Chase by 15 lengths.

April 1988: The pair land Aintree’s Chivas Regal Cup at a canter.

April 1988: Old rival Kildimo is prevailed in Sandown’s Whitbread Gold Cup.

October 1988: A 15-length comeback win in Wincanton’s Terry Biddlecombe Challenge Trophy.

December 1988: Sandown’s Grade One Tingle Creek Chase over two miles proves no obstacle to ‘Dessie,’ who produces an electrifying performance.

December 1988: The flamboyant front-runner shows his versatility by landing a second King George at Kempton – a race over three miles.

January 1989: In a great weight-carrying performance, Desert Orchid wins Ascot’s Victor Chandler Chase by a head.

February 1989: Desert Orchid returns to Sandown to win the three-mile Gainsborough Handicap Chase.

March 1989: Desert Orchid’s finest hour as he lands the Cheltenham Gold Cup in a thriller.