He was born 26 December 1786 in Westminster, London, and named for his father, George Osbaldeston, a member of parliament for Scarborough.

His father, born George Wickins, inherited the Hutton Buscel estates from his uncle Fountayne Wentworth Osbaldeston and adopted his name.

His father died in 1793; from age 6, George and his three sisters were brought up by their mother, who despite being a great political hostess, was wildly extravagant and squandered much of his inheritance.

He won one of the two seats, despite the machinations of his agent, who, claiming he had not been paid his fees, accused his own candidate of electoral malpractice, resulting in a trial.

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.

Osbaldeston won his bet, although the coach was loaded with a number of hefty Life-Guardsmen and despite being sent back from the bottom of Ludgate Hill for a false start.

An outstanding Single Wicket player, he was chiefly associated with Marylebone Cricket Club (MCC) but he also represented Surrey, Sussex and Hampshire.

An anecdote demonstrates the passion with which he pursued "the hunt": "Just when, in 1809, the 24 year old fourth Lord Monson was warming to the task of keeping his pack of foxhounds amongst the best blood in the country, nature accounted for him.

The gentlemen of Lincolnshire cast around for a new master and up turned one of those adventurous amateurs whose exploits with hounds and the ladies either break or make a hunt.

George Osbaldeston was 25 and he soon fell out with everyone except the foxes which he pursued with great noise, energy, boastfulness, courage and determination, to the far corners of the country.

"[8]The money he made from racing wins were overshadowed by gambling debts of around £200,000 (equivalent to £2,536,413 in 2023), which eventually forced him to sell his lands in 1848 and led to his dying almost penniless.

He was also known for his romantic escapades, such as attempting to seduce a friend of his mother's, Lady Monson (an unrequited love affair, despite his claims that she was the one woman he had really loved), staying at the house of a friend and seducing both his daughters on the same night, and leaving a ball for two hours to pick flowers from his garden for a lady there.

Of his brilliant beginning and impoverished end, his great friend and rival Horatio Ross commented, "He was open-hearted and trusted others; he was constantly deceived and robbed, and when his affairs were getting into confusion, he had not the moral nerve to pull up in time; nor had he a sufficiently business-head on his shoulders to guide him safely out of his troubles.

"[6] He died on 1 August 1866 in St John's Wood, London and was buried in the Williams family grave on the west side of Highgate Cemetery (plot no.11014).

Eventually George Osbaldeston Green and Mary Ann moved to the Gippsland area of Victoria.