Conditional jockey Jack Sherwood was born on January 26, 1992, the son of former jockey Simon Sherwood, famous for winning nine out of ten rides on Desert Orchid. He is also the nephew of Grand National-winning trainer Oliver Sherwood. 

Jack began as an amateur and rode eight point-to-point winners. Having turned conditional, he was crowned champion of the Racing Excellence Conditional Jockeys Training Race Series in 2013, a series for conditional jockeys who had ridden less than 20 winners at the start of the season. Two jockeys – Jack Sherwood and Killian Moore – were battling for the title going into the final race, held at Plumpton on 12th May.

Jack prevailed, winning the race aboard the Oliver Sherwood-trained favourite Drum Valley. 

He rode as a conditional jockey for two champion trainers, firstly for Nicky Henderson and then Paul Nicholls. It was for Nicholls that he enjoyed his finest hour when landing the Martin Pipe Conditional Jockeys’ Handicap Hurdle on Ibis Du Rheu at the 2016 Cheltenham Festival.

He also enjoyed plenty of success on two other Nichols-trained horses. He rode Present Man to win four chases during the 2016/17 season including Wincanton’s Harry Dufosee Challenge Cup and the Grade 2 December Novices’ Chase at Doncaster.

He won five races on Silsol including the 2015 Welsh Champion Hurdle and the 2016 Grade 2 West Yorkshire Hurdle at Wetherby. He also finished third on Silsol in the 2016 Rendlesham Hurdle and rode him in that year’s Grande Course de Haies d’Auteuil (French Champion Hurdle), finishing eighth behind stablemate Ptit Zig.

However, he endured a torrid season in 2017/18, managing just two victories from 77 rides. The last of those came on Glanvilles Guest for trainer Nick Mitchell in a Newton Abbot mares’ handicap hurdle on June 15, 2018.

He had what was to be his final ride on Made For You for Olly Murphy, finishing fourth of six in a Stratford novices’ hurdle on June 1, 2019. The following month he announced his decision to retire at the age of 27 due to a lack of opportunities and a gradual disillusionment with the sport. During a career spanning almost ten years, he partnered 63 winners under rules.

Of quitting the saddle he said: “It’s hard to walk away from something you love but I’ve reached a certain age and the riding is not going in the right direction and packing it all in is something I’ve had in the back of my head for a little while.

“You just get to a point when you think there’s no logic in continuing down the same old path. I consider you’ve got to be 100 per cent driven in anything to do well, and if it’s only around 50-50 or so then there’s not a lot of point in keeping up the pretence.”

Reflecting on his career, he said: “I’ve had some really great times riding and I want to say a massive thank you to Paul Nicholls for giving me so many chances when I was lucky enough to be based at his yard. Without him the big-race successes aboard the likes of Ibis Du Rheu, Silsol and Present Man wouldn’t have happened.”

As for the future, he added: “I’d like to stay in racing if the right job came along but, in all honesty, it’s an open book as to what I do next and I’m looking at all options.”

He now works for a property company in London.