Owner John Manley believes Dick Turpin's relaxed demeanour will help him last out the extended mile and a quarter of the Juddmonte International at York next Tuesday.
Manley stumped up £50,000 to add the classy miler to the Group One field at Wednesday's confirmation stage.
And he feels it will be money well spent as he will make a profit as long as the Richard Hannon-trained colt, second in the English and French 2000 Guineas and winner of the Prix Jean Prat, finishes in the first three.
"I gave it some thought and I was encouraged by Richard Hughes in my decision to supplement him," Manley said.
"I went through everything and it appeared to me that if he got placed I'd get my money back.
"If he was in the first three I'd make a profit and if we are fourth I'd lose fractionally. It's a bit like having an each-way bet at 3-1.
"I'm confident he'll stay because both Richard Hannon and Richard Hughes are fairly convinced he will, though his pedigree doesn't suggest that.
"That prompted me, along with his impressive run at Chantilly also, that we should have a crack at it. He's so relaxed at the races and is a real professional horse.
"I think there is always this, may I say it, hype with the Coolmore horses. Rip Van Winkle is, of course, a superb racehorse and deserves to be favourite.
"Interestingly enough, Richard Hughes said to me the other day that he thought Canford Cliffs had a harder race against Dick Turpin in the St James's Palace than he did against Rip Van Winkle in the Sussex Stakes.
"Everybody has given me encouragement, that's the reason I've ducked out of France.
"All his two-year-old races were on soft ground. I think he's a few pounds better horse on the soft. That said, he's also acted on good and good to firm ground, so he will take his chance on that."
Italian raider Jakkalberry, winner of the Gran Premio Di Milano, will be one of the outsiders for the Group One contest and connections are under no illusions about the task ahead.
Cristiana Brivio, wife of the trainer Endo Botti, said: "He did his last piece of work on Tuesday and everything went well, so the plan is to come to England.
"The horse will leave Italy on Friday night, stay for one day in Deauville and arrive in York on August 16.
"It will be much more difficult than the Group One that he won in Milan. He seems to have improved but he needs to for this sort of race.
"It is a very big step up. The horses in the Juddmonte International will be much better than those in the Gran Premio Di Milano.
"But the owner wants to try and give him a chance. It is a dream for him.
"He has won in heavy ground but he definitely prefers good ground."
Overturn will "almost definitely" take his chance in the totesport Ebor at York next week after delighting trainer Donald McCain in a recent workout.
Despite being campaigned through the winter, the six-year-old remains very much at the top of his game, winning the Scottish Champion Hurdle, the Northumberland Plate and the Galway Hurdle in recent months.
McCain was concerned a trip to the Knavesmire may be one race too many, but he can see no reason not to let him take his chance while he remains in rude health.
"We've left him in the entries and it is more than likely that he will take his chance," said Cholmondeley-based McCain.
"He was a bit subdued for a couple of days after Galway but I think that was more down to the travelling than anything else.
"Since then, he's come back really well and he worked really nice on Wednesday morning, so as it stands at the moment, we're almost definitely going.
"He's had a busy time but he seems to thrive on his racing, is in tremendous nick and it's a big prize to go for.
"He recovered from the Galway run quicker than I expected and if he does run next week, Eddie (Ahern) will ride him again."
Overturn is one of 57 remaining entries, with the Barry Hills-trained Tastahil left at the top of the weights following the defection of the Luca Cumani-trained trio Manighar, Drunken Sailor and Purple Moon.
Leading contender Harris Tweed has been confirmed, but is an expected absentee as connections accepted their charge was unlikely to make the cut for the famous Knavesmire handicap.
Richard Hannon's Martyr currently heads the market and remains in the field, as do other leading fancies such as Fortuni, Anhar, Hanoverian Baron and Dangerous Midge.