Time For Rupert an example of never looking a gift horse in the mouth

In December 2007 a marine insurance underwriter, with no experience of racehorse ownership, bought an unraced three-year-old liver chestnut gelding by Flemensfirth as a 10th wedding anniversary present for his wife. On such decisions can a previously solid marriage founder.

Time For Rupert an example of never looking a gift horse in the mouth
Time machine: Time For Rupert is making a name for himself in the novice chase ranks Credit: Photo: PA

However the ‘present,’ Time For Rupert, has won six of his 12 starts, was the only hurdler to make Big Buck’s break into a sweat last season, has paid for his purchase price three and a half times over and, it would appear, Toby Drysdale is good for another 10 years.

On Wednesday the six year-old looked in great shape as he had three progressively sharper canters up Paul Webber’s all-weather gallop. On Saturday at Cheltenham he will, three years on, return to the scene of his purchase as the most promising young staying chaser in the country for the DRS Contracts Novice Chase.

“I know how rubbish men are at anniversary presents,” admitted Drysdale on Thursday, “so I was looking for something a bit different. A neighbour took us to a summer evening meeting at Towcester and I was in the queue for a drink when the runners thundered past.”

That was Drysdale’s eureka moment. “But I thought I’d better run it past Sarah because I realised something like that could all go horribly wrong!”

A nephew of Californian-based trainer Neil Drysdale, he rang his uncle who suggested Webber as a trainer which tied in well because his yard was only 40 minutes from the Drysdales and they were keen to see the horse occasionally. “When we got to the top of the drive at Cropredy Lawn and saw it all laid out in front of us, I thought ‘absolutely.’” he added.

Also in the Littlecote Racing partnership are Drysdale’s parents-in-law Bob and Margaret Gardiner and Christine Dandridge and her husband Robert Romanes.

“We had eight horses on our shortlist and a budget of 35,000gns,” recalls Webber. “Time For Rupert was the first of them in and at 35,000 we were out but Bob said he’d pay the extra if we went to 40,000gns and we got him. Paul Nicholls was the underbidder and the other seven on our list all made well over 40,000gns. We were very lucky.”

His last four starts have been at Cheltenham, including his debut chase win last time and his second to Big Buck’s in the World Hurdle. “Having seen him in the breeze-ups we knew he acted there before he’d even run,” joked Webber. “The thing about him is that he’s phenomenally tough and very resolute. He always looks under pressure in a race, never travels on the bridle but he comes around that last bend, lowers his head and does his best.”

Webber, who is enjoying something of a renaissance, added: “I said to Toby a year ago when we thought he’d be handicap hurdling that it would be his ‘quiet’ season but, after going off a bit too quick with Lough Derg and getting tired first time out, he had recovered in two days. He won his next and again, two days later, he was mad fresh.”

Success now presents different worries for Drysdale. Given his line of business he is not sure which is worse; frost at Cheltenham or hurricanes knocking over oil platforms in the Gulf of Mexico. “This week it’s frost at Cheltenham,” he admitted.