Rupert Wakley

Rupert James Wakley was born on August 22, 1974, the son of former National Hunt jockey Nigel Wakley. The family moved to the Cotswolds when Rupert was four years old. He was educated locally and stayed in the area until moving to Newmarket, as an assistant trainer.

He rode his first winner on Who’s Next, trained by Lorna McGowan, in the Robert Hoare Memorial Novices’ Hunters’ Chase at Fakenham on Easter Monday, April 17, 1995.

Aged 21, he joined Kim Bailey’s Lambourn stable and rode eleven winners during the 1996/97 season, in which he had his first ride in the Grand National on 150/1 outsider Hillwalk. They pulled up just after completing a circuit.

Rupert improved his score to 29 the following season, the highlight of which was his victory on the Tim Forster-trained Wandering Light in the four-mile National Hunt Chase at the 1998 Cheltenham Festival. He also rode Kim Bailey’s Kamikaze in that year’s Whitbread Gold Cup, finishing seventh. He became Fegentri world champion amateur rider and finished second in the British amateur riders’ championship, beaten by Seamus Durack.

He turned professional at the start of the 1998/99 campaign and rode a total of 35 winners, a score which he bettered by one in 2001/02, registering 36 wins. His major successes included the Vulrory’s Clown Handicap Chase at Doncaster on Kim Bailey’s Bertone on December 11, 1999, and Sandown’s Agfa Diamond Handicap Chase on Bailey’s Trouble Ahead on February 5, 2000. He also won both the Swedish and Norwegian Grand Nationals on Trinitro.

He rode in three more Grand Nationals: on Druid’s Brook (66/1), unseated rider at the 12th in 2000; You’re Agoodun (28/1) brought down at the Canal Turn in the 2001 melee; and Carryonharry (66/1), who fell at the first in 2002.

Sadly, injury intervened and curtailed Rupert’s career. He had recurring problems with his shoulders, which kept dislocating. He had five operations on them but each time he came back they were not really stable. His final season in the saddle was 2002/03, during which he rode 16 winners. However, that season finished early in January and he underwent an operation to ‘tie in’ both shoulders after they became so loose that one or the other would pop out while riding a finish.

Rupert went to New Zealand that summer to stay with former colleague Tom Jenks, who had bought a 350-acre stock farm a couple of hours south of Auckland. Tom owned 200 sheep, 200 cattle, two pigs and a few horses. Wrestling sheep, using a chainsaw and putting up fencing during a five-week period provided a fitness test of sorts for Rupert and while the left shoulder was as good as new the right one still felt wobbly.

He returned to see his specialist later that year and the prognosis wasn’t good. The surgeon couldn’t see how it was going to rectify itself unless Rupert stopped falling off horses. That was hardly an option for a jump jockey. Aged 29, his ten-year career which had yielded just short of 250 winners was at an end. He thought long and hard about training but had seen so many of his weighing room colleagues struggling with 20 horses, working seven days a week. Rupert was after a job where he could afford to have a horse for pleasure, rather than relying on them for his income.

An old point-to-point friend, Rupert Sweeting, suggested an estate agency. That led him to the Knight Frank Worcester office in August 2004. After a spell in both the Worcester and Stratford-upon-Avon offices, he was promoted to Partner and Head of office. In November 2013, he was given the opportunity to head up a new office in Stow-on-the-Wold, a challenge which he has thoroughly embraced.