
Look at any information about the Cheltenham Festival and you’ll hardly fail to find out which jockey has won the most races and which trainers have seen their horses win more times than their rivals. When it comes to the owners, however, the information is far more difficult to come across. They don’t take the centre stage in the same way as the people who ride and train the entrants of the big races.
Horse racing is a complicated business in that sense. The owners are responsible for the purchase of horses and for deciding which trainers to send them to, but don’t tend to get the same degree of credit as jockeys and trainers. They’re an integral part of the process, with some even going so far as to having specific jockeys attached to them, but are a distant third in terms of importance in the racing world.
Given most owners don’t make money from racing it is worth celebrating those that have persevered and stand out as the best in Cheltenham history.
The Owners

The world of horse racing is a fickle business, with lists of ‘top’ competitors in any particular branch like to change at short notice. Whilst the Cheltenham Festival only takes place once a year, there are enough races within the meeting to mean that an owner could shoot up this list fairly quickly.
J.P. McManus
John Patrick McManus, better known as “J. P. McManus”, was born in Limerick, Ireland on the 10th of March 1951. He started life working at a plant hire company, later becoming an on-course bookmaker at a greyhound racing track. Hid first horse was Cill Dara, the purchase of which kick-started McManus on a career path that would earn him millions.
He enjoyed his first winning horse at the Cheltenham Festival in 1982 when Mister Donovan won the Novices’ Hurdle. The victory came at the fifth time of action, given that McManus had first stood in the paddock as an owner in 1978. He took the colours of his local GAA Club, South Liberties, meaning that his horses race in gold and green.
In the years that followed his success grew and grew, earning him the nickname ‘The Sundance Kid’. Nowadays he works from an office in Geneva, though he still has roots in Ireland. The mansion that he had built next to his Martinstown stud is the largest private residence in the country.
Known for his philanthropic work as much as for his success in horse racing circles, McManus saw seven of his horses win at the 2020 Festival. That took his total number of winners up to 66, which is fair and away the most of any owner during jump racing’s most prestigious event. Even an historical argument with Alex Ferguson will never take the shine of J. P. McManus’s success.
The Johnson Family
If J. P. McManus is the owner for the modern day then the Johnson Family is very much a group of owners from the past. David Johnson, the family patriarch and the man to whom most of their success is owed, was one a bank clerk earning just £9 per hour. He went on to become a multi-millionaire in the finance sector, buying horses as a hobby.
He focussed his interest on jump racing and saw Comply Or Die win the 2008 Grand National at Aintree. Whilst that might well go down as his greatest single victory, he was named the National Hunt Owners Champion six times between 1998 and 2008, offering proof of the fact that he was more than just a flash in the pan when it came to his skill at buying horses.
His best season was the 2004-2005 one, during which he owned 111 winners when working with the trainer Martin Pipe and the jockey Timmy Murphy. Not a bad return for someone who actually began his career buying flat racing horses. Part of his success was undoubtedly down to the fact that he worked regularly with A. P. McCoy, the successful jump jockey.
As with any jump racing connoisseur, his true love was Cheltenham Racecourse. Our Vic won the Gold Cup for him in 2005, with another five of his horses winning the race in the years that followed. He died on the 6th of July 2013, with the Johnson Family having secured its place in Cheltenham folklore.
Gigginstown House Stud
One of the most famous names in horse racing ownership, Gigginstown House Stud is part of a wider organisation that is owned entirely by Michael O’Leary, the Chief Executive Officer of Ryanair. It operates under the title of Tillingdale and was originally Tillingdale Limited, having been founded at the turn of the millennium.
It started out as a company providing horse breeding services and furniture management under the Gigginstown House Stud moniker and in 2003 O’Leary Cabs was added to the company. This provided an excuse for O’Leary to use bus lanes in Dublin, which is something normally reserved for buses and taxis.
The taxi firm might be something of a joke, but O’Leary’s interest in horse racing most definitely isn’t. Tiger Roll is arguably his most famous horse, having won four races at the Cheltenham Festival and back-to-back Grand Nationals, becoming the first horse since Red Rum to pull off the feat in the Aintree race.
His relationship with the Cheltenham Festival has always been one of joy, but certainly the win for War of Attrition in the Gold Cup in 2006 cemented it. He got another Gold Cup win with Don Cossack a decade later, though sadly the horse never ran again because of an injury. The wins will drop off in the years to come, with O’Leary deciding to wind down his racing operation.
The Stewart Family
There are a number of reasons why Andy Stewart and his family find themselves on this list, but one of the main ones has to be that they were the owners of Big Buck’s. Whilst it’s an exaggeration to suggest that the horse single-handedly put their name amongst the others here, but four consecutive wins in the World Hurdles certainly helped.
He was one of the best staying horses in the history of the sport, which is perhaps why so many are willing to overlook the errant apostrophe in his name. Andy Stewart had been a drop out when he began his career in the Square Mile as a broker, but that didn’t stop him making a success of himself, regularly featuring on the Rich List in the modern era.
His horses run in black, white and red colours, with the Cheltenham Festival being one of his favourite meetings. He sponsored the Supreme Novices’ Hurdle in aid of Spinal Research, which became a subject close to his heart when his son broke his neck whilst skiing in 2008. It’s a sign of how closely tied his love of horses has been with the meeting.
His advancing years meant that other members of his family began to become more prominent in the horse owning side of affairs. The Stewart Family enjoyed its first Cheltenham Festival winner in 2008 when Celestial Halo won the Triumph Hurdle. The first, but definitely not the last, including successive victories in the Foxhunter Chase for Pacha Du Polder.
Mrs Diana L Whateley
When it comes to successful owners, few are as difficult to find information about as Mrs Diana L Whateley. We know that her horses run in navy and light blue, for example, and that her husband, Grahame, is the chairman of a number of public companies in the United Kingdom, but other than that she tends to stay out of the papers.
That means that she allows her horses to do the talking, such as during the Cheltenham Festival in 2011. Back then, her and Grahame returned from a week skiing in Val d’Isere just in time for the meeting. It was worth their while coming back and heading straight to Prestbury Park, considering they had eight runners over the four days.
That included Menorah, who was the favourite heading into that year’s Champion Hurdle. In the end he finished a disappointing fifth, failing to live up to the promise that he’d set when winning the Supreme Novices’ Hurdle the year before. He was a horse that finished his career in style, though, and is indicative of the sort of horses that the Whateley’s tend to buy.
Horses like Captain Chris and Wishfull Thinking have ran in the Whateley colours, representing the cause well over the years. Grahame Whateley made his money in property, so it’s somewhat appropriate that the couple have built such an impressive horse racing empire. They might not have won as many of the big races as other owners, but loads of smaller wins get them on this list.