Vanity Fair

Winning Post: Jockeys John Osborne, Tom Cannon, John Watts, Fred Webb, Fred Barrett, George Barrett, William Robinson, and Fred Rickaby, with Sir Astley and Judge Clark in the background. By the racing caricaturist LIB (Liberio Prosperi).

In 1888 Liborio Prosperi, an Italian caricaturist who specialised in racing, drew his fantasy race for Vanity Fair with eight of that year’s most successful jockeys, amassing 615 wins between them. He also included two notable figures - John Francis Clark, racing judge and architect of grandstands, notably at Chelmsford, and one of the greatest patrons of the turf, Sir John Astley. Astley, a decorated officer of the Scots Guards, was a pillar of Newmarket’s community during the second half of the 19th century, and ironically given the nickname ‘The Mate’ as he was perceived to possess a nautical air. He was elected to the Jockey Club and established the Astley Institute, a social club for stablemen which exists today.

Jockeys from Left to Right
John Osborne was a highly popular and very successful jockey riding for nearly 46 years. In 1888 at the age of 55 he won the 2,000. Father to 13, he was awarded 3600 guineas on his retirement from a nationwide testimonial fund, equivalent to more than £1 million in today's money.

Tom Cannon was Champion Jockey in flat racing and also crossed over to the jumps, winning the Grand National in 1888. He went on to be a trainer and tutor to numerous successful jockeys. He was father to the six times Champion Jockey Morny Cannon and great grandfather to Lester Piggott, and unusually ended his days at the venerable age of 72.

Jack Watts rode his first winner at the age of 15 in 1880. He continually battled with his weight and never attained the prize of Champion Jockey although he did make runner up in 1891. He retired as jockey to train in 1900 but died 2 years later from a lifetime of ‘wasting’.

Frederic Webb was a Champion Jockey who went on to train for numerous well known owners at Newmarket including Lillie Langtry and Lord Shrewsbury, and later was employed as trainer for Prince Thurn and Taxis in Hungary.

Fred Barrett was a jockey known more in turf history for his failures than his victories with a reputation for erratic riding. However in 1888 he was the British Champion Jockey with 108 wins, just narrowly beating his brother George. He went on to be a trainer but died at 27, again from a lifetime of ‘wasting’.

George Barrett had ridden 3 winners at Newmarket by the age of 15 and although always pipped to the post for Champion jockey, from 1879-1894 he rode over 1400 horses to win, with another nearly 2500 coming 2nd and 3rd. A savvy investor amassing a considerable fortune, he too died from a lifetime of ‘wasting’ at 35.

William ‘Jack’ Robinson, jockey turned trainer, is best remembered for his part in the Craganour affair. Passing the post first in the 2000 Guineas, one judge declared the 2nd placed horse the winner. Craganour’s owner was the unpopular Charles Bower Ismay whose father’s White Star line flagship Titanic had sunk the year before, and whose brother having survived was known as the ‘coward of the Titanic’. At the 1913 Derby, the very same where suffragette Emily Davison was killed, Craganour won again only to be disqualified. Robinson was said to be left broken by the affair and died not long after.

Fred Rickaby was described as the soundest and most hard-working jockey of his generation. His father was a trainer and his son Frederick Lester was following in his footsteps with a growing list of wins before enlisting in the Veterinary Corp in 1916. He died in the final days of WWI at 23 and his younger sister named her son after him. Lester Piggott went on to be one of the greatest jockeys of the 20th century with wins alone of 4, 493.