His father Simon rode the iconic grey Desert Orchid to Cheltenham Gold Cup glory in 1989, one of the great races in National Hunt history, and his uncle Oliver saddled 2015 Grand National winner Many Clouds.
Sherwood, 24, is now making a name for himself following a succession of high-profile Saturday successes including Silsol’s win in Wetherby’s prestigious West Yorkshire Hurdle on Charlie Hall Chase day which prompted talk of a challenge at next year’s World Hurdle at the Cheltenham Festival before the horse suffered a slight injury setback.
Victory on Lifeboat Mona soon followed at Ascot, then a stirring success on the ever-popular Rocky Creek at Sandown in a handicap-defying performance under top weight in the colours of the Johnson and Stewart families, two of the sport’s leading owners.
The conditional showed great acumen to win Doncaster’s Grade Two novice chase on Present Man, a horse unsuited by Town Moor’s left-handed configuration. Always in the vanguard, Sherwood was nerveless in the saddle as his pursuing rivals closed ominously on the run to the final fence. Despite a slightly wayward jump, he had judged the pace to perfection – his father and uncle would have been proud – in a race which fortuitously enjoyed terrestrial television coverage on Channel Four to further advertise the in-form jockey’s credentials.
Even greater challenges await last Saturday’s winner. Champion trainer Paul Nicholls is tempted to run Present Man in Kempton’s Grade One Kauto Star Novices Chase, formerly the Feltham, on Boxing Day because the track will suit and connections will have nothing to lose if the brilliant Thistlecrack lines up in the contest.
With nine wins already this season, Sherwood is on track to beat his previous career-best tally of 14 as he finally fulfils his potential following a stop-start career that began with Venetia Williams. An unproductive spell with Nicky Henderson followed, not helped by injury and a lack of opportunities, before a more fruitful move to the Ditcheat stables of the all-conquering Nicholls – arguably the most driven man in racing.
Though opportunities have to be earned, Nicholls did not hesitate to make full use of his battalion of young riders – Sherwood included – when stable jockey Sam Twiston-Davies suffered a serious spleen injury. Team Ditcheat’s camaraderie between riders is discernible, the rivalry intense but friendly, with Present Man’s success followed by stablemate Cliffs Of Dover winning the Grade Two Summit Juvenile Hurdle under top conditional Harry Cobden in the colours of Mirfield businessman John Cotton.
Sherwood says the trainer keeps things simple – he was happy for Present Man to make the running at Doncaster against more illustrious opposition and was quick to praise the jockey afterwards.
“Paul is a genius for placing horses in the races where they have the most realistic chance of winning. It’s why he’s been champion trainer so many times,” said Sherwood. “He talked about the race beforehand, I wasn’t sure there was much pace, and he was happy for me to make it. He just said ‘well done’ afterwards and talked about the Feltham.
“When the job came up, I had to take it. You only have to look at his record and how he gives young lads a chance. If you can take them, it is to your advantage. My last five rides for Paul have all been winners.”
There is no shortage of advice at the disposal of Sherwood, who won this year’s conditional riders’ race at the Cheltenham Festival aboard the Nicholls-trained Ibis Du Rheu when he fulfilled his dream to win a race at the signature meeting where his father became a household name thanks to his headline-making exploits with Desert Orchid.
Sherwood’s house-mate is champion point-to-point rider Will Biddick, the aforementioned Twiston-Davies is a lifelong friend while Sherwood senior is still involved in racing as clerk of the course at Ludlow.
Brought up watching videos of the mud-splattered Desert Orchid galloping up the Chelteham hill, and the late Sir Peter O’Sullevan’s spine-tingling “He’s beginning to get up” commentary as the grey reeled in the luckless Yahoo on monsoon-softened ground, the jockey says his racing ancestry is a mixed blessing.
“A bit of both,” he says. “It opens doors – but people expect you to be the finished article, but it’s not always like that.
“Tom Scudamore is riding better than ever, but people expected him to be as good as his father Peter at 18 or 19. My recent wins at Wetherby and Doncaster have certainly helped – I just want to keep on learning and improving.”