“Unable to get a race in Tennessee, Uncle Berry took his horse to Natchez, Miss., traveling through the swamps of the Chickasaw and Choctaw Nations, and entered him in a stake, three mile heats, $200 entrance; but his bad luck pursued him, and just before the race his horse snagged his foot, and he paid forfeit. He remained near Natchez twelve months and nursed his horse as no other man could have done, until he was perfectly restored to health and in condition for the approaching fall races of 1808. Writing to Col. George Elliott, he urged him to come to Natchez and bring fifteen or twenty horses to bet on Omar, and also to bring Monkey Simon to ride him, which Colonel Elliott did.
“Simon’s appearance on the field alarmed the trainer of the other horse, who had known him in South Carolina, and, suspecting that Omar was a bite, he paid forfeit.
“As Simon was a distinguished character, and made a conspicuous figure on the turf of Tennessee for many years, it may be well to give some account of him. His sobriquet of ‘Monkey Simon’ conveys a forcible idea of his appearance. He was a native African, and was brought with his parents when quite young to South Carolina, before the prohibition of the slave trade took effect. In height he was four feet six inches, and weighed one hundred pounds. He was a hunchback with very short body and remarkably long arms and legs. His color and hair were African, but his features were not. He had a long head and face, a high and delicate nose, a narrow but prominent forehead, and a mouth indicative of humor and firmness. It was rumored that Simon was a prince in his native country. I asked Uncle Berry the other day if he thought it was true. He replied, ‘I don’t know; they said so, and if the princes there had more sense than the rest he must have been one of ’em, for he was the smartest negro I ever saw.’ Colonel Elliott, speaking of Simon after his death, said he was the coolest, bravest, wisest rider he ever saw mount a horse, in which opinion Uncle Berry fully concurs.
“Simon was an inimitable banjo player and improvised his songs, making humorous hits at everybody; even General Jackson did not escape him. Indeed, no man was his superior in repartee.
“On one occasion Colonel Elliott and James Jackson, with a view to a match race for $1,000 a side, a dash on two miles, on Paddy Carey against Colonel Step’s mare, consented to lend Simon to ride this mare.
“Colonel Step not only gave Simon $100 in the race, but stimulated his pride by saying they thought they could win races without him, whereas he knew their success was owing to Simon’s riding. Somewhat offended at the idea of being lent out, and by no means indifferent to the money, Simon resolved to win the race, if possible; and nodding his head, said: ‘I’ll show ’em.’ The mare had the speed of Paddy and took the track, and Simon, by his consummate skill and by intimidating the other rider, managed to run him far out on the turns, while he rested his mare for a brush on the stretches.
“On reaching the last turn Simon found the mare pretty tired, and Paddy, a game four miler, locked with her, and he boldly swung out so far as to leave Paddy in the fence corner. The boy came up and attempted to pass on the inside, but Simon headed him off, and growled at him all the way down the quarter stretch, beating him out by a neck. Simon could come within a hair’s breadth of foul riding and yet escape the penalty. Colonel Elliott lost his temper, which he rarely did, and abused Simon, saying, ‘not satisfied with making Paddy run forty feet further than the mare on every turn, he must ride foul all the way down the quarter stretch.’
“The Colonel repeated these charges until at length Simon answered him with, ‘Well, Colonel Elliott (as he always called him), I’ve won many a race that way for you, and it is the first time I ever heard you object to it.’”
Much has been said and written of the tenderness and care bestowed by the Arabs on their favorite horses, but I doubt whether any Arabian since the time of the Prophet ever showed such devotion to his favorite steed as Uncle Berry to the thoroughbreds under his care. In fact, his kindly nature embraced all domestic animals. For many years he resided on a rich, productive farm near Gallatin, where he trained Betsy Malone, Sarah Bladen and many other distinguished race horses; raised fine stock and fine crops and proved himself to be one of the best farmers in the neighborhood. He had pets of all kinds—huge hogs that would come and sprawl themselves to be rubbed, and game chickens that would feed from his hand, and followed him if he left home on foot, often obliging him to return and shut them up.