The rank of Colonel which this Irishman was entitled to assume was procured by him in a characteristically curious way. In 1760, when the county of Middlesex was very backward in raising sufficient men for its militia, a well-known Scotch adventurer, MacGregor by name, whose family had suffered a good deal for the Stuarts in 1745, seeing a good opportunity of making some money, set about raising a regiment in Westminster which the Government promised to recognise as soon as three-fourths of the commissions should be filled up. He found, however, difficulty in obtaining officers and had to ransack the town and hold out commissions to all sorts of people, amongst whom was O'Kelly, who became an ensign, in due course of time rising to be Lieutenant-Colonel. O'Kelly, though totally ignorant of discipline, is said to have presented the most soldierly appearance of any officer in the regiment. This was not saying much, for the third captain was a tea-dealer, the fourth a tailor, and the fifth a boatswain's mate who had bought an ale-house with prize-money and could just sign his name. The most junior officer was a crippled creature of foreign extraction. When O'Kelly became a major, he is described as having put his regiment through certain military evolutions to the entire satisfaction of the King and his staff, whilst his Lieutenant-Colonelcy was celebrated by a splendid entertainment which many of the aristocracy of Leicestershire attended. O'Kelly was sometimes known as Count O'Kelly, a title which was supposed to have been conferred upon him by his fellow-prisoners during a sojourn in the "Fleet" when he was a young man. Here he met Catherine Hayes, who lived as his faithful companion through life. Though she was never married to him, her position was more or less recognised, and O'Kelly left her an annuity which she continued to enjoy till she died, in the second decade of the nineteenth century, at the age of eighty-five. Among many racing successes O'Kelly won the Derby twice--in 1781 with Young Eclipse by Eclipse, and three years later again with Sergeant by Eclipse out of Aspasia. His racing colours were scarlet and black cap. Whilst there is no doubt but that O'Kelly was very lucky in much that he undertook, his originality and penetration were largely responsible for a success which, however, never gained him admission into fashionable circles.