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.
Though a hospitable man of a certain genial humour, O'Kelly was not very open-handed to dependents. In spite of his affluence he was even mean enough to keep jockeys of the poorer class out of their money, season after season, being sometimes even sued by them in the law courts, and personally dunned on the race-course stands. In such a place, on one disgraceful occasion, an old sportsman made the Captain look extremely small by apostrophising him as a mean, low-lived, waiter-bred skunk. In spite of these failings O'Kelly achieved a certain popularity by the good dinners and excellent wines which he provided at his house at Epsom, his dry and truly Irish facetiousness affording the highest zest to those entertainments. At his country house he would never allow any betting or gambling. A constant subject of jest amongst his familiars was the tone in which at dinner he used to say, "John, bring the aaples," meaning the pines, and the whimsicality with which he would apostrophise his servant on certain occasions. The latter having announced the non-arrival of fish, "Begorra," said his master, "and if you can't get any fish, bring herrings." O'Kelly was a gentlemanly and even graceful man in behaviour, a strong contrast to his bear-like figure, dark and saturnine visage, with the accompaniment of his rough striped coat and old round hat. A quite peaceable man, though a true-bred Milesian, O'Kelly never had the smallest appetite for fighting with any weapon whatever. He was a great contrast in this respect to the bullying Dick England, with whom he once became involved in a law-suit. He was ambitious of honour and distinction, a proof of which was his successful pretension to military rank. In the darling object of his life, however, capricious fortune left him in the lurch; the Jockey Club, whose action in this matter was generally approved, steadily refusing to admit among them a parvenu, not, perhaps, of unequivocal character. This O'Kelly, so much of a philosopher in other things, did not possess philosophy enough to forgive, but, in revenge, never failed to characterise the honourable body which refused to admit him by the very hardest professional names which his wit and bitterness could devise.
Very much aggrieved at not being admitted into certain of the Clubs at Newmarket and in London, which were frequented by aristocratic sportsmen, he never lost an opportunity of retaliating on those whom he deemed responsible for his exclusion.
On one occasion, when making an arrangement to retain the services of a certain jockey, he told him he had no objection to his riding for any other person provided he had no horse running in the same race; adding, however, that he would be prepared to double his terms provided he would enter into an arrangement and bind himself under a penalty never to ride for any of the black-legged fraternity. The consenting jockey saying that he did not quite understand who the Captain meant by the black-legged fraternity, the latter instantly replied with his usual energy, "Oh, by ——, my dear, and I'll soon make you understand who I mean by the black-legged fraternity:—there's the Duke of G., the Duke of D., Lord A., Lord D., Lord G., Lord C., Lord F., the Right Hon. A.B.C.D., and C.I.F., and all the set of thaves that belong to their humbug societies and bug-a-boo Clubs, where they can meet and rob one another without detection."
This curious definition of the black-legged fraternity is a sufficiently clear demonstration of how severely O'Kelly felt himself affected by his rejection. He made a point of embracing every opportunity of saying anything to excite the irascibility of the sporting aristocracy, whilst shirking no difficulty or expense to obtain that pre-eminence upon the Turf which he eventually enjoyed. Dining at the stewards' ordinary at Burford races, in the year 1775, Lord Robert Spencer in the chair, Lord Abingdon and many other noblemen being present, matches and sweepstakes as usual, after dinner, were proposed and entered into for the following year—amongst the rest, one between Lord A. and Mr. Baily, of Rambridge, in Hampshire, for 300 gs. h. ft., when the Captain was once or twice appealed to by Mr. B. in adjusting the terms, and Lord A. happened to exclaim that he and the gentleman on his side the table ran for honour, the Captain and his friends for profit. The match was at length agreed upon in terms not conformable to the Captain's opinion, and consequently, when he was applied to by B. to stand half, he vociferously replied, "No, but if the match had been made cross and jostle, as I proposed, I would have not only stood all the money, but have brought a spalpeen from Newmarket, no higher than a twopenny loaf, that should (by ——!) have driven his Lordship's horse and jockey into the furzes, and have kept him there for three weeks."
His support of and attachment to Ascot was strikingly conspicuous. During the races there he ran a horse each day for years, whilst his presence and his pocket enlivened the hazard-table at night.