1 Gianluca Vialli
No wonder he couldn’t handle Watford’s limited budget properly — Gianluca Vialli had never had to worry about money before. His building magnate father was a self-made millionaire and his childhood home was a 15th-century castle in Lombardy with more than 60 rooms. No surprise, either, that when Watford gave him his company car, he wondered where the chauffeur was. The youngest of five children, Vialli was emotionally and financially indulged, and when he decided that he wanted to leave school at the age of 15 to become a footballer, his parents’ reaction was not the one that might normally have been expected in such circumstances. Papa didn’t cut him off without a penny; instead, he indulged his boy’s fantasy, no doubt believing it would all come to nothing. From there, showing more grit than might have been predicted, he won 59 caps for Italy (the total might have been higher had he not played the hilarious public-school practical joke of putting grated Parmesan in manager Arrigo Sacchi’s handkerchief) and every European trophy during his time with Sampdoria, Juventus and Chelsea.
2 Princess Anne
Always more keen on horses than, say, people — “The horse is about the only person who does not know you are royal,” she once observed — and keener on riding horses than, say, working for a living, the Princess Royal decided not to go to university, in order to concentrate on her equestrian career. She won the individual European Three-Day Event at Burghley in 1971 and was voted BBC Sports Personality of the Year. In 1976 she competed in the Montreal Olympics, where she made history by being the first athlete too posh to have to submit to a then-mandatory sex examination. In 1988 she joined the International Olympic Committee — an institution made for those with sufficient time on their hands to gallivant around the world at other people’s expense while deciding that, yes indeed, Atlanta is a suitable place to hold the Olympic Games.
3 Johnny Dumfries
He might have been plain old Johnny Dumfries to his motor-racing chums, but to Who’s Who he will always be Sir John Colum Crichton-Stuart, who was born in Rothesay Castle in Scotland, home of the Bute family, who were festooned with both lineage and money. Not wanting to trade on his family name, he pretended to be a painter and decorator and by 1983, as a 25-year-old, he was battling with fellow posh boy Ayrton Senna in Formula Three. After a season in Formula One (scoring three points) he won Le Mans — a race from which the working classes are banned — in 1988 and then retired in 1990 to become the Marquess of Bute, the Earl of Windsor, Viscount Ayr, Lord Crichton of Sanquhar & Cumnock, Viscount Kingarth, Lord Mountstuart, Cumrae & Inchmarnock, Baron Cardiff and, of course, Viscount Mountjoy. Now there’s posh.
4 Prince Alexander Obolensky
Post-1917, princes weren’t popular in the Soviet Union. Lucky, then, that Prince Alexander Obolensky was spirited out of the country to north London by his father, an officer and adviser to Tsar Nicholas II. From there, Alexander, who was intellectually gifted and no stranger to the company of women, went to Oxford University and, having gained British citizenship, was selected for England’s rugby union side, scoring 17 tries for Great Britain against Brazil in 1936 and, later that year, two in the game that marked England’s first triumph over the All Blacks. An RAF pilot in the second world war, he died in 1940 while practising take-offs.
5 Sir C Aubrey Smith
A surgeon’s son, Cambridge University cricket captain and freemason, Smith was pronounced dead while prospecting for gold in South Africa in 1888. A year later he made his only England Test appearance (as captain), taking seven wickets for 61 runs. He was over 50 when he moved to Los Angeles to found the Hollywood Cricket Club. (“When the grand old man asked you to play,” said David Niven, “you played.”) He became the film industry ’s British colonel of choice and was knighted in 1944.
6 Ayrton Senna
Nothing, save caviar emporia and the Orient Express, welcomes the posh with such enthusiasm as Formula One. Brazil is a country of the very rich and very poor. No prizes, then, for guessing on which side of the electric fence Ayrton Senna grew up. His father, Milton, was a rich landowner (just the 90,000 acres, grazed by 10,000 cattle) who noted that little Ayrton had dreadful co-ordination, even for a four-year-old. To remedy the problem, Milton went to the car component company he owned and told them to build Senna Jr a motorised kart. The problem was solved and Ayrton was soon driving one of the family’s many cars. A racing career was born, but only after family finances enabled him to compete in Europe.
7 Prince Albert of Monaco
While giving every impression that bending down to tie his own shoelaces would be too Herculean a task for him, Albert turns out to be quite the sportsman. A black belt in judo, he also competed with the Monegasque bobsleigh team in the Calgary, Albertville, Lillehammer, Nagano and Salt Lake City Winter Olympics. Medal-free, he quit after Salt Lake City, where the only team minuscule Monaco could beat was Taiwan.
8 Bobby Jones
No mere golfer, Jones was a renaissance man: a legendary intellect, famed designer of such courses as Augusta National and in all aspects of his life a Southern gentleman. The son of a prominent Atlanta lawyer, young Bobby was so refined that he could not keep down solid food until he was five. The family’s summer home was near a country club, and it was there that he developed his golf skills, qualifying for the US Amateur Championship at the age of 14. By 28 he had retired to tend the family fortune.
9 Marquess of Queensberry
Not technically a sportsman, more a wife-beating, semi-literate, alcoholic thug. But Oscar Wilde’s Scottish nemesis was very, very posh indeed. John Sholto Douglas, the 8th marquess, was a boxing promoter who in 1869 endorsed and sanctioned (but did not write) the 12 rules of boxing, to ensure the sport remained a noble art and the preserve of gentlemen. As Law 5 stated: “A man hanging on the ropes in a helpless state, with his toes off the ground, shall be considered down.”
10 Colin Montgomerie
When Monty joined the Scottish amateur golf circuit, he struggled to understand why the other chaps were hostile. He was Scottish, wasn’t he? True enough — but they hadn’t been educated at the super-posh Strathallan school in Perthshire, where the pupils all wore kilts. Nor was their daddy the former secretary of Royal Troon. Nor did they live in a mansion overlooking Troon. And nor, finally, did they have a posh English accent.
