Monbeg Dude foiled a Welsh National plunge on Teaforthree to provide the Scudamore family with its latest victory in a race that for three generations has had their name indelibly stamped on it.
The eight-year-old gave fledgling trainer Michael Scudamore not only his first success in the stamina-sapping contest but also his biggest career triumph.
Michael's grandfather, also Michael, was successful in the 1957 running, while his father Peter rattled off four wins in his days as stable jockey to Martin Pipe.
Ridden with poker-cool confidence by Paul Carberry, Monbeg Dude was saved until the final fence to make his winning move.
Favourite Teaforthree finished a half length second with Triggerman another 11 lengths third.
Michael Scudamore, who at one time dreamed of becoming an international rugby union player, said he hoped the victory would act as a testament to him and his team's ability to produce winners.
He is based at Bromsash which is 10 miles short of the Welsh border.
"There's Welsh on my grandfather and mother Maz's side and I played open side flanker as an under-19 in Wales, when I made the first team at Ebbw Vale," Scudamore saids.
"I played a lot of club rugby but was never big enough."
Two of Monbeg Dude's owners also have a rugby attachment in Nicky Robinson (who plays for Wasps) and James Simpson-Daniel (Gloucester and England).
Scudamore revealed that there was a family difference of opinion as to whether Monbeg Dude would compete in the Chepstow race.
"My dad and all the owners wanted to come here, but I wanted to go back to Cheltenham on New Year's Day as I thought this might be too big an ask for the horse.
"It was an interesting discussion but Dad said we were going to the Welsh National ... obviously I'm delighted we did.
"Hopefully this real boost will show people we can do it as long as we get the right ammunition."