George Osbaldeston: The Squire who was one of the greatest all-round sportsmen

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George Osbaldeston (born December 26, 1786) was the archetypal British sporting squire, aptly nicknamed simply ‘The Squire’.A versatile all-round sportsman, compulsive gambler and life-long philanderer, he was one of the most colourful characters of early cricket. Arunabha Sengupta looks back at the life and career of this gentleman of leisure.

The Squire

He was called ‘The Squire’. Indeed, he could scarcely have been called anything else.

Through his life, he was the image of the archetypal British sporting gentleman. He excelled at shooting. He was a champion all-round cricketer, a fabulous hard-hitting batsman and a fearsome fast underarm bowler. He was even more celebrated as a steeplechase rider, and was a renowned Master of Fox Hounds. And he was a compulsive gambler and womaniser.

Much of the stories of his life and exploits are known through his fascinating autobiography. Along with all his flairs, The Squire did not really suffer from false modesty.

George Osbaldeston was born into money, at Osbaldeston House near Scarborough, Yorkshire. His father George Wickins, a Member of the Parliament, had inherited the Hutton Buscel Estates from his uncle Fountayne Wentworth Osbaldeston, and had adopted his name. The Squire’s mother, Jane, was the daughter of Sir Thomas Head of Langley.

Osbaldeston’s father passed away when he was only six. The only son amongst five children, our man inherited a vast fortune. And indulged by his spendthrift mother, he set out to live the next few decades as the quintessential moneyed English gentleman. He spent his time sporting and drinking, and excelled at these pursuits. He also gambled and womanised, and he was not quite as successful at these.

The early years set the tone of Osbaldeston’s life. He went to Eton as was expected of a boy of his background. His days there were brief, stormy and his accomplishments singularly non-scholastic. Before he was expelled, he could boast, “I could beat any boy single-handed at cricket, and any boy my age in fisticuffs.”

While at Eton, he also nurtured his liking for shooting, fishing, making fireworks, rowing, hiring horses in Windsor, and going to Ascot races.


After being forced to leave Eton, he spent a ‘wild spell’ at Brighton at a crammer’s. It was here that he acquired his first pack of hounds. At Oxford, he hunted, annoyed the master of Brasenose College to the verge of being sent down from there; and, before leaving without a degree after three years, became a tearaway fast bowler.

It was now that his mother, a great political hostess, pushed him into politics. In 1812, Osbaldeston was elected the Whig MP for East Retford. However, he found politics a great bore and seldom attended Parliament. Later he wrote: “I was so entirely engrossed with hunting, shooting and athletic feats that I could not turn my thoughts to politics, and it was only in response to my mother’s entreaties that I attended the House on urgent occasions.”Yes, by then he had found his great love.

The Cricketer

In 1808, Osbaldeston played for MCC for the first time. He also became a celebrated Master of Fox Hounds. And he became one of the leading riders in the land. His racing abilities in flat, steeplechase, endurance and carriage races earned him plenty of fame and purse. He remained a celebrated rider till he was nearly 70. And with time he became a famed master of hunts including Quorn, Pytchley and Atherstone. For thirty five seasons he was the master of various packs, and no more fearless man led a pack of hounds until a shooting accident impaired his nerves. As a game shot he was never surpassed, and once he brought down 98 partridges out of 100 shots.

It was mainly due to the extravagance of his mother, a characteristic inherited and continued by him, that he lost his estate. It only increased his aggression,cultivateda fierce ambition for sporting success and nurtured jealousy for anyone with a title. His racing successes brought him plenty of money, but he lost much more through gambling. And infamously he locked horns with Lord Frederick Beauclerk, the other famed gentleman cricketer at MCC.

Osbaldeston was a gifted strokeplayer and an underhand bowler of genuine pace. Only George Brown bowledfaster than him, and later Arthur Haygarth bracketed both Osbaldeston and Brown alongside the fast bowlers who operated with the new-fangled round arm fashion.

In 1816, Osbaldeston hit 112 and 68 at Lord’s for MCC against Middlesex. The following year, he made 106 against Epsom for Sussex, sharing a huge stand with William Lambert. And his bowling put wicketkeepers as much at peril as batsmen. Indeed, many a stumper stuffed their shirts with straw while keeping to Brown and Osbaldeston.

His all-round abilities meant that for a considerable part of his career he was second only to EH Budd as a single-wicket player. And Budd and he developed a lifelong friendship comparable to Keith Miller and Denis Compton, or Shane Warne and Kevin Pietersen.

However, in spite of hi brilliance, Osbaldeston is remembered for on field controversy as much as he is for the colourful episodes of his off-field life.

In 1810, Osbaldeston teamed up with Lambert to take on Lord Beauclerk and Thomas Howard in a double wicket match. On the day of the contest, Osbaldeston woke up sick. When a postponement was asked for, Beauclerk was his characteristic unsporting self. “Pay or play,” was his answer. Hence, Osbaldeston tottered to the wicket, scored a single and retired. Lambert made 56, caught Beauclerk off his own bowling for 21 and bowled Howard for 3. He went in again to score 24 and then bowled Beauclerk for 18 and Howard for 24, thus winning by 15 runs. This left Beauclerk seething. Unfortunately, he had a long and unforgiving memory.

The animosity for titled individuals did not help Osbaldeston’s relations with Beauclerk. In 1817 they flared again, when Osbaldeston played for a Nottingham XI against an England side captained by Beauclerk. There were plenty of shady incidents in the match, players of both sides had been purchased. It is not clear whether Osbaldeston was really involved in the underhand dealings, but Beauclerk thought so. Besides, after this fixture he gave vent to his long pent rage about the double wicket match by banning Lambert from MCC.

And then came Osbaldeston’s infamous boast that he could beat anyone in single wicket. When George Brown of Sussex bowled furiously fast and defeated him, a disgruntled Squire scratched his name off the list of MCC Members. Later he repented and asked to be reinstated. Beauclerk, who virtually ran MCC, would have none of it.

However, in spite of such episodes, Osbaldeston remained one of the leading cricketers of his day, one of the cleanest hitters of the ball and an underarm fast bowler of genuine pace. He scored over 1000 runs in First-Class cricket at a creditable average of almost 19. He is also recorded with 45 wickets, 16 catches and a stumping.

The rider

Yet, Osbaldeston’s greatness as a sportsman was perhaps more as a rider.

In 1826, he won 1000 guineas for a steeplechase against Dick Christian.

In 1831, he rode 200 miles in 8 hours and 42 minutes using 28 horses. “The Squire, dressed in purple silks and black velvet cap, set off at 7.12 am. and despite several rain showers, one fall and generous stops for brandy and food, achieved the 200 miles in less than 9 hours riding 28 horses. He then rode back to Newmarket, bathed and joined his friends for dinner.” 162 years later, on the same course, the champion jockey Peter Scudamore only just managed to beat the squire’s record although his breaks were much shorter and he spent more time in the saddle. On completing the 200 miles Scudamore declared himself exhausted and ‘laid himself carefully on the ground for a massage’.

In 1836, The Squire bet £200 with Lord George Bentinck over a race he won easily. When His Lordship was slow to settle the money by claiming that Osbaldeston had been less than straight in the affair, The Squire’s friction with the titled men came to the fore. The Squire and the Lord met at dawn, pistols drawn, on Wormwood Scrubs. Osbaldeston was a crack shot unlike Lord Bentinck, and the duel could have ended in only one way if it had been properly contested. But, it is conjectured that his lordship’s friends negotiated a compromise and both parties missed their mark.

On another occasion Osbaldeston won a 100 guinea bet against Paul Methuen by driving a stage-coach from St Paul’s churchyard to Greenwich, with the vehicle full of hefty Life-Guardsmen.

He competed in his last race when he was 69.

As a shot, as already noted, he was unparalleled. Osbaldeston used a gun with a bore of 1½ inches. And he did not only shoot partridges. On one occasion, the notorious Lord Bentinck fired his pistol in the air while watching a race. Osbaldeston, who was taking part in the race, responded by shooting Bentinck cleanly through his hat. It was a warning shot.

Foxes and Women

The Young Squire: photo courtesy Thurgarton History

The Young Squire: photo courtesy Thurgarton History

But if he was to pick one of the sporting pursuits, it would probably have been the hunt. Osbaldeston never enjoyed himself more than when bounding with the hounds at Quorn and Pytchley.

It cost him a lot, in stables, kennels, men, acres and lodgings. Along with his enormous gambling debts, it was another passion which left him nearly penniless at the time of death. But, Osbaldeston would not give it up for anything.

The other obsession of Osbaldeston was womanising. In Lincolnshire he courted the recently widowed Lady Monson, a friend of his mother’s. It was unsuccessful and the lady went ahead and married Lord Warwick. However, Osbaldeston maintained that she was the love of his life.

Later Miss Ann Green of Lincoln had a long relationship with The Squire. In his autobiography, Osbaldeston describes Ann Green as ‘a member of the frail sisterhood’ or in other words a prostitute. In 1812, a son was born to them, out of wedlock. Mother and son moved to Tasmania. This son, George Osbaldeston Green, fathered 16 children. Many of them died in infancy, but The Squire was left with a large number of grandchildren.

It is also rumoured that at one county ball, Osbaldeston seduced both the daughters of the house in one evening. His affairs were many, but mostly casual and largely unsuccessful.

Osbaldeston’s gambling debts ultimately caught up with him. He lost around £200,000 on horses and sold the remainder of his estates in 1848 to settle his debts. He was rather impoverished, when in 1851, at the age of 65, he married the rich widow Elizabeth Williams. He lived in her Regent Park house until his death in St John’s Wood in 1866.

When he passed away, his lifelong friend EH Budd was heartbroken. “A noble fellow, always straight,” he summed up. The newspapers also waxed eloquent on his sporting deeds.

It was perhaps not quite accurate as far as descriptions of lives go.But, nevertheless, it had been an eventful life.