Winning the Boodles Cheltenham Gold Cup remains right at the top of Nicky Henderson's priorities as he prepares to saddle Shishkin in the latest instalment of the Cheltenham Festival's marquee event.

Henderson is no stranger to staring on the opening day of the Festival, winning day one’s feature Champion Hurdle a record nine times. But the Gold Cup has proved a tougher beast to tame for the Seven Barrows handler throughout his long and decorated career.

Nevertheless the Gold Cup has managed to find its way to Henderson’s Lambourn base twice in the race’s 100-year history, with the quest for a third success in the blue riband still paramount in his thoughts each passing season.

“As we’ve given up on the Grand National we may as well concentrate on the Gold Cup,” said Henderson.

“The Champion Hurdle and the Gold Cup are the most important races as far as I’m concerned because it means you have the best horse and that’s what a race is about.

“After I’ve had a horse a week I have owners asking which race I’m going to run it in at Cheltenham.”

It was not until 2011 that Henderson broke his duck in the Gold Cup when the heir apparent of the staying division, Long Run, slayed the mighty Ditcheat stalwarts Kauto Star and Denman and the baton of power was handed over to the keeper of Seven Barrows and his then multiple Grade One-winning six-year-old.

Long Run would fail to defend his title 12 months later, but Henderson had another Gold Cup winner steadily brimming away, and two years after a first victory in the final-day showpiece, Bobs Worth would prove to be the ultimate model of a staying chaser as he stormed up the Cheltenham hill in the hands of Barry Geraghty.

Those two treasured champions will always hold a special place in Henderson’s affections and are the gold-standard to which future Gold Cup candidates will be measured – with this year’s contender meeting his guvnor’s approval ahead of his date with destiny.

Henderson said: “I think Shishkin compares very favourably to Long Run and Bobs Worth and if you are only judging them on home work, well Bobs Worth was just an amazing character because he showed you nothing and was as laid back as Constitution Hill – he was just the nicest horse.

“On the racecourse he would just gallop and gallop and gallop until he could gallop no more.

“Long Run was a very classy horse, a very talented horse. Bobs Worth though was a trojan, a proper horse. Just a trier and what he lacked in ability he made up for in just heart.”

Like his handler, Shishkin himself has plenty of Cheltenham T-shirts hanging in the wardrobe and from four Festival starts has two victories and a silver medal to his name.

However, the one-time shining star of the speedy two-mile divisions now sees himself staring in the stamina-sapping three-and-a-quarter-mile Gold Cup endurance test.

Henderson, though, is not surprised he has ended up plying his trade in the staying ranks and said: “I think lots of horses have done the same, if you take Desert Orchid for example, he looked a two-miler to start with and plenty of them have done it and gone up in trip.

“You could say why didn’t we realise it earlier, but I think we did and Altior was the same – he got pigeon-holed as a two-miler and was the best, so we left him there.”

Shishkin’s journey to leading British Gold Cup hope has been far from straightforward since the days of his youth when Supreme Novices’ Hurdles and Arkles were a mere formality.

Always one to keep his handler on his toes – as shown when refusing to race at Ascot in his disastrous seasonal return – it seems Henderson has had to utilise all his years of experience to hack into the mindset of the 10-year-old.

That includes the King and Queen’s primary jumps trainer calling on a member of the royal family for assistance, with Shishkin spending his summer with Zara Tindall, blowing away some cobwebs before the serious business on the Lambourn schooling grounds begins.

Henderson explained: “He can be a bit of a ‘boyo’ and we actually sent him away to Zara Tindall for the first month to get him going and get his mind on the job instead of doing some easy trotting and build-up work here, because that is when he can be a bit silly.

“Once you get a run under his belt he is probably in our hands, while before that we are probably in his. That’s what he was like at Ascot but after that he’s been as good as gold. He’s always been like that.”

There has been no repeat of his Ascot misdemeanours in both of Shishkin’s outing since as he enhanced his Gold Cup claims firstly when unseating from a winning position in the King George VI Chase and then getting a confidence-boosting success under his belt in the Denman Chase.

Few would argue he would be even shorter in the betting lists if not for unseating Nico de Boinville shortly after the second-last at Kempton and Henderson has full confidence he will last the distance in his toughest assignment to date.

“He’s come out of Newbury really really well,” added Henderson.

“I think we are confident he will stay and Nico was happy enough in the King George to say ‘we’re not going quick enough, I’m going on’ and that was against proven stayers, so he was pretty confident he was going to stay.

“I think it’s an open Gold Cup and open enough to be in it. He deserves to be in it. He would have been first or second in the King George and I honestly think he would have won and that was a hell of a performance for his first run of the year, even if he finished second that is one hell of a trial.”