The eldest son of Mr Alexander Cunningham, Charles John Cunningham was born at Morebattle Tofts (on the very edge of the fatal field of Flodden) on December 21, 1849, Educated first at Edinburgh Academy then subsequently at a private tutor's, Charlie - as he was familiarly known - intended to pursue a career in the army, but the sudden, early death of his father thwarted and changed his plans.
He was obliged to take over the running of the estate and did so with much enthusiasm while retaining his love of sport. He would ride in a steeplechase at Kelso and ride to hounds with the Duke of Buccleuch's; he would fish on the Tweed and shoot game on the Border moors. He excelled on the cricket fields of Berwick and was a curler of great renown on the ice in matches on the Borderland.
Charlie first sported silk at in 1837, his racing colours being olive green, primrose hoops and red cap. His initial ride was over the old Border Hunt Steeplechase at Stodrig and, that year, he won eight of his sixteen races. It was an average which he was to maintain throughout his career.
He was fortunate in obtaining from a Russborough mare three horses - Percy by Hotspur; Merry Lass, a daughter of Laughing Stock; and Douglas, a son of Sincerity - and, with Charlie in the saddle, they won fifty-one races between them from sixty-eight attempts. Other well-known horses of his were Harlequin, White Cockade. Leap Year, King Charles and Why Not. Charlie always maintained that Why Not was the best. In 1895, Why Not won eight of the twelve races he contested but died the following year from inflammation of the lungs.
In one year, Charlie rode 52 wins out of 100 mounts; the following season he won 49 races out of 100, and, in 1886, 43 out of 76. He also had great good fortune in the National Hunt Steeplechase, winning it three times - on Dry Bread at Derby in 1882; Why Not at Highfield, near Malton in 1886; and on Harlequin in 1890, on which occasion the race was run in Scotland in conjunction with the Edgbaston Hunt meeting.
Considering that he stood over six feet one inch in his stockinged feet and that his average bodily weight during the seventeen years he was riding was over twelve stone, his achievements in the saddle were quite remarkable.
His Grand National record bears scrutiny. Charlie's first appearance at Aintree was in 1887, riding Old Joe, which had won the race the previous year. Old Joe (11st. 10 lbs.) was unplaced.
The following year on Bellona, he fell at the first fence after landing on the racecourse first time round.
In 1889, he and Why Not made their first bid for victory, just being beaten - by a length - by Frigate after a tremendous race from the last fence. The next year, starting at 100-9, Why Not fell at the fourth. Charlie quickly remounted to finish fifth behind Ilex. 1891 was another unlucky outing for the partnership; looking all over a winner, Why Not fell heavily at the second last. Charlie was so badly hurt that he had to be taken from the course by ambulance. Why Not was a very small horse and it was said at the time - and possibly with some truth - that Charlie, being long in the leg, caught his feet in the fences when jumping them and that this fact had something to do with his failures when riding him at Liverpool. Also, Charlie did not appear so much at home when riding against a large field composed of professional jockeys as he would do in Hunt Races, where there is more room, smaller fields, and consequently more time to look about.
Under Arthur Nightingall, Why Not at last won the Grand National - in 1894 at his fifth attempt.
Charlie had better luck in the Scottish Grand National and is the only jockey to have won the race on four occasions; Bellman (1881), Wild Meadow (1885), Orcadian (1887) and Deloraine (1889).
At Rugby Hunt on 29 March 1881, he rode six winners from seven rides. He began by guiding the evens favourite Starlight to an easy victory in the Farmers’ Maiden Plate, over three miles. He followed that with a four-length success on Bess in the Open Hunters’ Steeplechase. The third race was a £25 Match in which he had no mount. He then rode the next three winners, all odds-on shots: Baker Pacha in the Ladies’ Plate, Bivouac in the Hunters’ Selling Chase, and Starlight again in the Farmers’ Plate. The penultimate event was a Private Sweepstakes, in which he finished second on the 7/4 joint-favourite Sportsman. Then, in the last race, the Lilbourne Gorse Plate, he was reunited with Bess, who started at the prohibitive odds of 10-1 on and “won in a canter by a neck”. The achievement should perhaps be gauged by the strength of the opposition. Five of his six winners were hot favourites and in three of the races he faced only one rival.
In the final year of his life, Charlie (who was sometimes referred to as Black Charlie) won the Buccleuch Welter at Musselburgh on The Swan, which was recording its tenth consecutive victory.
Months before his death, Charlie underwent a serious surgical operation for spinal trouble. It was sad to see him, weeks, later, crippled and hobbling about at Kelso racecourse. This operation led to his early death.
Aged 56, Charlie Cunningham died at his residence, Muirhouseland, Kelso, on 20 October 1906.
His four hunters were sold by auction at Leicester Sales in late November for a total of 1,090 guineas.