Born and bred in Essex, Oliver Sherwood explains how his ‘parents amicably parted company when Simon and I were very young so we had two homes’. Splitting their time between their Mum’s in Warwickshire and Dad’s, who had remained in Essex, Oliver reflects on their ‘very good childhood’ doing lots of riding and Pony Club in both places. The aforementioned Simon is indeed the professional jockey who famously won the 1989 Cheltenham Gold Cup on Desert Orchid.
On being asked if he was a jockey, Oliver, 68, dismisses his career as a jockey with a quick, ‘I was heavier than Simon so I rode as an amateur over in Ireland and England’. Yet, his career speaks for itself: he was Champion Amateur in the 1979-80 season and during the ‘80s, won the Cheltenham Foxhunters’ twice on Rolls Rambler and Venture To Cognac, as well as an Aintree one on Spartan Missile. He also ticked off a Peterborough Chase, a Horse And Hound Cup and a Mildmay Novices’ Chase.
Oliver Sherwood now and when winning the 1980's Aintree Foxhunter's on Rolls Rambler
and the '84 Cheltenham Foxhunter's on Venture To Cognac
Oliver has been a loyal Lambournian for over forty-five years, taking over from Nicky Henderson as Assistant to the great Fred Winter and trained from there in two yards – starting up in Ronehurst in Upper Lambourn in 1984 and in 2021, moving to Charlie Mann’s Neardown Stables for two seasons until his retirement. After his first ever winner, The Breener at Newbury in November 1984, he’s trained up there with the best, again tallying up many of jump racing’s biggest prizes. Of course, he’ll always be associated with the brilliant galloping machine that was Many Clouds, who won twelve races. Owned by the late Trevor Hemmings, Many Clouds galloped into the hearts of many when winning the 2014 Hennessy and solidified his fans’ devotion when victorious in the ‘15 Grand National.
He trained an Aintree Chase winner in Coulton, a Tingle Creek in 1990 with Young Smugfit, six Cheltenham Festival winners and eight Grade 1 winners including Silver Wedge. The talented Cenkos won five, Rayvin Black won the 2016 Kingwell Hurdle and Puffin Billy won eight in total and was a true Ascot-specialist. His talented hurdler, Large Action won fourteen races, finishing third in Flakey Dove’s Champion Hurdle and second in Alderbrook’s. All in all, Oliver trained 1199 winners, over jumps and on the Flat, in the UK and in Ireland.
In an undulating couple of years, Oliver battled cancer and won. He continued to train – Queens Gamble won three out of her five starts, including a Listed bumper in November 2022 round Cheltenham. Yet, this spring, he announced his retirement – or partial retirement because he stepped into the role of assistant trainer to the young trainer Harry Derham: an old war hound advising the eager younger puppy. Inarguably, a wonderful decision because racing would be a poorer without one of its most dedicated and humble gentlemen.
With his wife of thirty years, Tarnya, Oliver has daughter Sabrina, 28 and son Peter, 26. From a previous marriage, he has another daughter Davina, 39, and son Archie, 36. Oliver and Tarnya also have a black and tan terrier, called Alby.
How did you get into racing? My father always had point-to-pointers and had a point-to-point course in Essex called Marks Tey. He had the odd Flat horse in Newmarket. My mother also did a bit of ‘pointing so both my brother and I could – the proverbial – ride before we walked. Besides, I was too thick to go to university.
What was it like watching your brother win his Gold Cup? Funnily enough, it was the one Cheltenham and Gold Cup Day that I didn’t attend as we had an issue at home. But, watching it from home was quite something; it was very very special. I wouldn’t tell Simon to his face but he was a good jockey.
Why did you start training? I started in 1984, in Lambourn at Rhonehurst and why is a very good question. I don’t know why. I’d done my apprenticeships in training – one year in Newmarket with Gavin Pritchard-Gordon, three years in Ireland with Arthur Moore and six years for Fred Winter.
I realised I was too heavy to be a professional jockey so it was the next step on.
What are your standout moments as a trainer? The first big thing was having a double at the Cheltenham Festival in 1988 with The West Awake and Rebel Song for long standing owners and friends. That was a special day.
Both Hennessy Golds Cups were very good – Arctic Call and Many Clouds, plus his Grand National. The obvious one will always be Many Clouds – that goes without saying. To get a horse like him late on in one’s career was a defining moment. I’ll always be known as a Grand National winning trainer – that will stick in one’s CV forever.
There are also the very good horses I had in my early days training: Large Action was placed in two Champion Hurdles and I had a really good young horse called Cruising Altitude, before she got injured in another Champion Hurdle. Young Pokey won an Arkle. I could go on forever but I was very very lucky.
Who was your racing hero? Vincent O’Brien by a country mile. He was a league above everyone else as in training Grand National winners then Derby winners. He was the Aidan O’Brien of his time.
Which jockeys have you admired? Over the years, not that many jockeys actually rode for me and I didn’t get through many so-called stable jockeys. Those who rode underneath my umbrella were my brother Simon, Jamie Osborne was good, David Casey who’s now Willie Mullins’ right hand man and obviously Leighton Aspell. AP McCoy rode about thirty winners for me.
Forgetting those for a second, John Francome was an ultimate horseman and AP was the ultimate jockey. There lies a difference!
Jamie Osborne stood out as a jockey and was brilliant but more brilliant on a Saturday than on a Monday afternoon at Plumpton. He excelled at the big meetings and he’s been a friend to me virtually since day one.
Jamie Osborne winning on Large Action in 1994
Did you have an underdog racehorse you always admired? The obvious one, I just mentioned, was a very very good horse, probably one of the best horses not to win a Champion Hurdle: Large Action. He won a Tote Gold Trophy but was second and third in two Champion Hurdles – even now, people know of him.
Another one would be Puffin Billy – despite him not being a natural jumper, I thought he was very good.
Coulton won at a Festival for Martin St. Quinton, the present CEO at Cheltenham Racecourse – he was potentially the best horse I’ve ever training but also wasn’t a natural jumper. He had all kinds of jumping issues and saw Yogi Breisner on the day of his races to have a school, but still won a Cathcart. He was definitely the most underrated of all my horses.
Coulton winning under Osborne in 1995
Favourite racecourse: I’m going to be boring and say Newbury because it’s so close to home and I haven’t got far to drive. As I’ve got older, the driving gets a bit monotonous, and seems a bit of a waste of time. Fontwell is a smaller course I will always be fond of. I’ve been very lucky there – it’s a cracking second division track.
Favourite meeting: Aintree would be my favourite, only because of the holiday atmosphere – people go and stay, whereas the Cheltenham Festival is full-on, going backwards and forwards each day, which is hard work as well as trying to train the horses. I love Aintree and, to be fair, I love going racing up north, they greet you with open arms. I enjoy Perth and the festival up there, and Carlisle is quite fun; as is anywhere we can stay away, not that I am shirking any responsibilities!
What were your reasons for retiring? It was one thing after another. About eighteen months to two years ago, I had lymphoma so was having chemo. This puts perspective on life. Then losing my friend Richard Aston, who we stayed with during Aintree for over thirty years, knocked the daylights out of me. Also, losing horses and numbers in the yard being less made it not financially viable.
Queens Gamble winning at Cheltenham
Photo Credit: Getty's Images
What are your thoughts about the future, especially your assistant trainer role? (Laughing) I’ve never had to work so hard in the whole of my life! No, Harry Derham is very very enthusiastic and I’ve known him and his family a long time. He’s got his uncle Paul Nicholls’ drive. He’s got that youthful exuberance and I’ll hopefully have that little bit of control on him and keep everything steady.
We got some very nice horses, which is great and I’m excited that we’ve got a lot of horses too. Trying to help someone young in the game and pointing him in the right direction is exciting.
What will you miss about training in your own name? You’ve just hit the nail on the head – I’ll miss the likes of Queens Gamble and some of ‘my’ horses that have been transferred to Harry from my name.
I won’t miss the business side of it and all the driving. Luckily, a lot of my owners have been very loyal and have come with me to Harry’s and the majority of my staff have joined Harry too, which is fantastic.
It’s a different area and different gallops, but it’s much the same and I have the same team around me, which is great.
Does racing have a positive future in relation to animal rights? They’ve got to stop pandering to them – not just in racing but in anything. How far do you go down the line, saying after you, after you? They don’t want racing however much you tell them about it. These horses are treated second-to-none, racehorses love it and without racing, Thoroughbreds would be extinct. You can argue with those people who want racing banned until you’re blue in the face – they’d agree that black is white – you can’t reason with them.
Favourite meal: Spring lamb, new potatoes and runner beans.
Favourite drink: I’m not really a drinker. Ever since I had lymphoma, I don’t like the taste of alcohol but if you had to pin me down, it’s a Moscow Mule.
Favourite holiday destination: The Amalfi Coast in Italy.
Favourite music: Anything by Olivia Newton-John and Paloma Faith.
Favourite movie: Pretty Woman.
Other hobbies: I love cricket in the summer and I like a bit of shooting in the winter. Basically, I love any sport but those two are my favourites.
*Many thanks to Old Gold Racing for the help in securing this interview. They published it first in their fabulous newsletter Racing Weekly. To sign up, go to https://mailchi.mp/2f6ba62d6182/racing-weekly-lead-capture
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