Dr. Syntax, a brown colt foaled in 1811 by Paynator out of a mare by Beningborough, was bred by Humphrey Osbaldeston of Hunmanby, Yorkshire, and sold as a yearling to Mr. Knapton of Huntington, near York, and subsequently to Ralph Riddell of Felton Park, Northumberland.
Dr. Syntax began racing in 1814 in the colors of Ralph Riddell and ran for ten seasons until 1823. His many victories included a sequence of seven in the Preston Gold Cup from 1815 to 1821, the only example known of a horse winning the same race for more than six seasons. It took the outstanding St. Leger winner Reveller to end the sequence when he beat Dr. Syntax in 1822. Dr. Syntax also won thirteen other Gold Cups, including the Lancaster Cup five times, and thirty five races in all. At stud he sired the great mare Beeswing, winner of fifty-one races and dam of two classic winners Nunnykirk and Newminster.
The Druid wrote of Dr. Syntax 'The Doctor, as they so fondly termed him in the North, was in every way a very remarkable horse to look at, being barely fifteen hands high, very broad at the base of the nose, with an eye as full and bright as a hawks, a high drooping rump and short quarters. He was very short in his coat which was mouse-colored. A slight canter would bring out his veins so strongly that he looked as if covered by network. He had splendid legs and a strong muscular head; but could never bear either whip or spur, but Bob Johnson (his jockey) could always get every ounce out of him by merely stroking and talking to him'.
The Hon. William Maule (1771-1852) the second son of George, 8th Earl of Dalhousie, went into politics and became a close friend of Charles James Fox and from 1805 held his seat as M.P. for Forfarshire for eight successive parliaments until he was called to the House of Lords as Lord Panmure of Brechin and Navar in 1831. Although a passionate follower of the turf, and a man of considerable wealth, Maule's only really successful horse was Ledstone. His link with Dr. Syntax is not entirely clear. He would have probably seen him on several occasions as he ran all over the North of England for several years.