Stories from the Saddle: Rupert Stearn

Rupert Stearn has been one of the leading jockeys in the East Anglian area for over 20 years and, despite focusing exclusively in recent years on riding horses owned by his family and longstanding friends the Turners, he has managed to notch up 127 victories between the flags and six in Hunter Chases, including two in 2025 at Fakenham. Father Simon is Clerk of the Course at Ampton, where sister Hetty is Fixture Secretary for the Suffolk meeting and – in advance of the season opener there on Sunday – Jake Exelby talked to Rupert about the connections he’s made, and the horses ridden in his long career… and potatoes !
 
Rupert going to post in his family colours (Graham Bishop)

 

Rupert going to post in his family colours (Graham Bishop)

How old are you and where are you from?

I’m 41 and am based at Wymondham in Norfolk. My parents moved here not long before I was born.

Based on lifetime wins, I believe you’re the leading current rider who doesn’t work in racing full-time. What do you do for a living?

I’m a farmer, 100%. We farm 2,000 acres, of which we own about half. It’s mostly arable, and mainly potatoes. I think we have about 500 acres of them, producing 12,000 tons a year, and it can be quite stressful at times.

 Talk me through your career in racing so far and how you got into point-to-pointing in the first place?

I was first plonked on a pony aged two and I’m from a horsey background – Mum and Dad both rode. My Mum, Penny, rode in one point-to-point. I think she fell off at the first and that was it! But she rode for Paul Cole on the flat – she was racing secretary to him, and to David Morley when he trained at Timworth, next to Ampton – and in the Newmarket Town Plate a few times.

 Dad got into horses through the Turners. He was a tenant at their farm in Ampton when (former champion jockeys) David and Josie were in their prime and started riding out for (their father) Joe. I think Dad rode about 30 winners in points as well as a few Hunter Chases at Fakenham and Folkestone. His best horse was Wise Gambol, who was hardly ever out of the first three (he had 31 top three finishes), but kept finishing second to Stanwick Lad.

So, riding ponies was natural when I was young and it snowballed from there. I did pony club, and show jumped to a decent level. I always wanted to be a jockey, and someone told me that showjumping was the best grounding. There was no pony racing in those days.
Rupert sports snazzy goggles as he wins at Ampton (Graham Bishop) 

 

Rupert sports snazzy goggles as he wins at Ampton (Graham Bishop) 
Talk me through your first rides… and your first win on Imperial Mist.

I had my first ride aged 16, in foot and mouth year, in a 15-runner Mens Open on Sorcerer’s Drum, a lovely schoolmaster. It was such a blur, and all happened so fast, that – going down the back straight – I didn’t know how many circuits were left. Nibby Bloom told me it was the final one, so I kicked on, and we finished second. I was ready to go again, but the season was called off a week later.. George Cooper – who owned and trained Imperial Mist – had been a family friend for many years. He was still riding at the time but gave me a few opportunities. I won seven races on Foulstons Ruler for him.

 I believe you went to work for Philip Hobbs for a time. How did that go?

So, the annual described me as a ‘promising 17-year-old’, did it? I don’t know what happened since! I had ambitions to turn professional, so thought it would be a good place to go to get experience.
The other lads put my mattress on top of my car on the first night (luckily Rupert wasn’t on it at the time), and it seemed to rain nearly every day, but it was great fun and there were lots of pubs! It was a good era for horses – Rooster Booster won the Champion Hurdle when I was there – but I didn’t get a ride for Philip, so went to Harper Adams College for a year, then back to the farm.

 In the early years, as well as George Cooper, many of your winners were for Caroline Fryer and Robert Abrey. Who were the best horses you rode for them.

Caroline was a neighbour of ours, so gave me rides. She had the likes of Ballygalley Bob and Ide No Idea, who my wife Ali still has at home.
The best I rode for Robert were Coat Of Honour, Cosmic Sky and Forget The Ref. Of course, Robert bred (multiple Grade One winning chaser) Edwardstone. I rode her mother, Nothingtoloose. She was no good, so he put her in foal and look what happened!
Rupert on Forget The Ref

Rupert on Forget The Ref

And more recently, you’ve had a productive association with the Turners. Tell me about your links with them.
As I said, we’ve known the family since Dad worked at Ampton. James Owen used to ride for them but had a fall and broke his ankle, so I stepped in for a few weeks. Then, when James retired, I started riding for them more, but Ed (Turner) was still riding at the time, so I was his number two!
Rupert riding for the Turners in the Kingston Blount sunshine (Hattie Austin)

 

Rupert riding for the Turners in the Kingston Blount sunshine (Hattie Austin)

What has been your career highlight?

My Hunter Chase double at Fakenham on Easter Monday 2009 on Bonne Noel’s for James Owen and Robert’s Coat Of Honour. Bonne Noel’s was James’s first winner as a trainer under rules and was the rank outsider. James was riding the favourite but pulled up!

Which has been your favourite horse? And the best one you rode?

The best was Clara Sorrento… easily. My favourite was probably Rocja, a little gem of a horse we had at home. I won five on him, and he was a hardy, tough horse – the sort who used to bite you in the stable!
 

Recently, your family-owned horses have been in training with the likes of David Kemp and Jenny Owen. What was behind the decision not to have them trained at home?

It’s quite simple. I’ve never had the same ambition to be a trainer as a rider – riding’s always been far ahead in terms of satisfaction – and I’ve never been the best of trainers! We’ve been lucky enough to have some nice horses and want to get the best out of them. Jenny Owen and David Kemp do the job very well and are both local. I’ve also bought a couple from the Owens in recent years and decided to leave the horses with them.

 

Which current pointer (not one of your own mounts) would you most like to ride?

Winged Leader, whose career I’ve followed in Ireland. He seems to win every week (he’s won 38 races), and I’d love a ride on him.

Over here, I remember your own Broken Eagle. When I rode against him round Cottenham and Higham, I couldn’t see how anyone could get close to him. I’d have paid you for the ride!

Rupert (in black and white) trying to keep up with Broken Eagle (Neale Blackburn)

 

Rupert (in black and white) trying to keep up with Broken Eagle (Neale Blackburn)

Which other jockeys do you admire? Both contemporary and retired.

A standout – although long-retired – would be my father. I always used to go and support him and would stand by the fence – it was exciting to see him ride.
Of current riders, the numbers don’t lie, so it would be Gina Andrews and Will Biddick, who’s only just retired. I don’t know the riders as well as I used to. In Ireland, Derek O’Connor – who I’ve ridden against over here – is unbelievable.
 
Derek O'Connor at Chaddesley Corbett - unbelievable (Pointing WM)

 

Derek O’Connor at Chaddesley Corbett – unbelievable (Pointing WM)
Do you think your children will follow you into the saddle?
Maybe. Bunny is eight and Albert is six, and they’re both already riding.
Bunny and Albert may follow in their father's footsteps

 

Bunny and Albert may follow in their father’s footsteps
What’s your favourite course?
Fakenham. It’s the only course in Norfolk, my favourite race is the Queen’s Cup Hunter Chase (which Rupert has won three times), which is held there, and I like playing golf in the middle of the track!
 
Rupert winning on Clara Sorrento at Fakenham - best horse, favourite course (Graham Bishop)

 

Rupert winning on Clara Sorrento at Fakenham – best horse, favourite course (Graham Bishop)
What do you enjoy most about pointing?
It takes you back to the bare bones, with the thrill of participating in an adrenalin-fuelled sport with your friends at the weekend. For five or six minutes you’re emulating your heroes, the likes of A P McCoy and Richard Dunwoody. What makes the sport fantastic is that it gives opportunities to people like me.

 You’re now one of the senior jockeys in the weighing room. What changes (for better and worse) have you seen over your time?

For the better, the ground conditions – I used to ride when they couldn’t water. The introduction of young horse maidens is another positive. It gets us competitive with the Irish both in the sales ring and under rules, where it’s great to see British pointers winning at the top level.
For the worse, the lessening of the link between pointing and hunting is a massive shame. I used to be a keen hunter. And a lot of my friends have stopped riding – the likes of Andrew Braithwaite, George Greenock, Ben Rivett and, of course, Ed Turner.
 
The Turner family (Ed is second right) - great friends with Rupert (Caroline Exelby

The Turner family (Ed is second right) – great friends with Rupert (Caroline Exelby)

What do you think will happen to pointing after a hunting ban?
It won’t be easy to keep the show on the road, and I think there will be fewer meetings, amalgamations and more club fixtures. But I hope things can carry on.

 What would you do if you were in charge of the sport?

This is a difficult subject. Pointing’s gone down a professional route, which I don’t think can be reversed. So, I think we could look at allowing licensed trainers to have a limited number – say five to ten – pointers in their yard, like they do in Ireland. Most of the top pointing yards are professional anyway and giving licensed trainers an easier way in might help in giving rides to young jockeys and a second career for older horses. It wouldn’t be a bad way to boost numbers.

 What would you be doing if you weren’t involved with horses?

I’d probably grow more potatoes!

 What are your non-horsey hobbies?

I support both Manchester United – which is painful at the moment – and Ipswich, who I go and watch every so often. I also follow Formula One.
Then we run a small shoot at home four or five a year for family and friends.

 Is there anything else you’d like to say?

I’d like to thank my whole family – Mum, Dad, my wife and my sister – for all their support over nearly 25 years, especially Dad for always saying, ‘I’ll get you another horse.’ And I’d also like to think everyone I’ve ridden for, from George Cooper to the Turners. We’ve had some great days.
 
Rupert at Horseheath after yet another victory (Graham Bishop)

 

Rupert at Horseheath after yet another victory (Graham Bishop)
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Pointing People: John Sharp

Few, if any, people do more to support point-to-pointing in East Anglia than John Sharp. Based at Dullingham near Newmarket and a former rider with a distinguished career, counting 168 winners between the flags alone, he also finds time to run a successful horse feed business, Sharp Nutrition, alongside his pointing duties. A former Chair – and now Vice President – of the PPORA, John also acts as Clerk of the Course at Horseheath and Chair of the Thurlow Hunt. Jake Exelby talked to him in advance of the forthcoming fixture at Horseheath on New Year’s Eve.
John with Caroline Bailey at the National Awards

John with Caroline Bailey at the National Awards

How did you get into point-to-pointing?
My first rides were on Paradise Beach at Cottenham in the late 1960s – the horse was about the same age as me and would only last two-and-a-half miles. I was terrified – I remember Hunter Rowe swearing at me, “Don’t you ever come past me, boy.”
I wanted to be a jockey so had two years as amateur for George Owen in Cheshire when Tommy Stack rode for the yard and rode in points against the likes of Robin Greenaway. Because I wanted to turn professional, I went to be second jockey for Les Kennard in Somerset, then went to work for Stan Mellor near Lambourn, who told me I wouldn’t make it, so I went home, which was on the border of the Midlands and East Anglia areas, to ride in points.

 Tell me about your equine feed business.

I founded it in 1997, after leaving Dodson and Horrell, where I’d helped start their thoroughbred division. I knew people in Newmarket through my riding and mostly supply studs – my leading customer among trainers is Harry Eustace.
I used to supply Shadwell Stud – Hamdan al-Maktoum’s death left a big dent – and my largest client is David Redvers and Qatar Racing.

Christmas is our busiest time of the year, as most people don’t hold more than a week’s worth of stock, so we have to keep delivering. We’re spoilt this year – we normally only have two days off, but Christmas Day and Boxing Day lead into the weekend!

 Horseheath has a (deserved) reputation as a fair, staying track, with many using it as a stepping stone to Cheltenham. Why do you think that is?

Apart from being right-handed, I think the two courses are very similar. Both have hills and hollows, uphill and downhill fences, and both have a downhill back stretch and a climb to the finish.
Action from Horseheath (Graham Bishop)

Action from Horseheath (Graham Bishop)

What improvements have you made to the track during your time as Clerk of the Course?

We were unable to race in 2014. There was a new farm director on the Thurlow Estate who thought it would be a good idea to mole-drain the course but shouldn’t have done it in the summer and didn’t realise there would be a problem. The root system died and there were brown lines across the track. The ground – which is normally a lovely cushion – was false, you couldn’t ride faster than a canter and, walking the course, your stick would go in six inches. The three hunts who raced at Horseheath held a joint meeting at High Easter that year and we got the course back by drilling, rolling and disking, working on it until the root system recovered. We were able to race as usual in 2015. Then, after the 2017 season, we moved the last fence on the downhill stretch, which used to cause problems – I called it a ‘jockeys fence’. The horses would be motoring by that stage and – coming past the wood and noticing the new reservoir – they could lose concentration. So, we moved the two downhill fences closer to the bend at the top of the hill, to slow the horses down. The second fence is now 250 yards further back than it used to be.

You moved the February meeting at Horseheath to November this year and it was abandoned due to low entries. Why do you think so few horses entered?

One reason is that people aren’t ready with their horses. Another is that all the numbers are dropping. When I moved to East Anglia 25 years ago, there were 19 fixtures – now there are ten.
Owners are going under rules – you can win £350 even if you’re unplaced – and there’s less of an incentive to have pointers. And as well as clamping down on trail hunting, the government isn’t being helpful to English farmers and agriculture.
I hope we don’t plan to run in November again next year, because I think the same thing will happen.

 Which jockeys have you most admired?

I grew up following David Turner – literally. I had great respect for John Bryan, to whom I was third in the jockeys title in 1978. Alan Hill was bloody good in his time and Gary Hanmer was one of the toughest.
Nowadays, I like to watch Dale Peters and Jack Andrews, and Alex Chadwick has won a lot of races for us. Alex and Jack have both turned professional now and will be a loss to our sport.
Alex Chadwick (with Gina Andrews) on Ragnar Lodbrok (Graham Bishop)

 

Alex Chadwick (with Gina Andrews) on Ragnar Lodbrok (Graham Bishop)

Who have been your favourite horses?

Water Sport was the best I ever rode, and one of the best pointers in the country at the time. I won 30 races on him, but he only ever won at Worcester under rules. Stanwick Lad was the most prolific – we won over 40 together – but he was another who couldn’t cope with the bigger fences and only won twice under rules.
 
John on Stanwick Lad

John on Stanwick Lad

What are your favourite courses?
I loved Newton Bromswold. It was set in proper grassland, and we would race across seven different fields. I also had a lot of success at Cottenham and Higham.
 
The parade ring at Cottenham, where John enjoyed plenty of success (Graham Bishop)

The parade ring at Cottenham, where John enjoyed plenty of success (Graham Bishop)

What have been the highlights of your time in the sport?

Winning the RE Sassoon Hunter Chase twice on Kelly’s Honor and finishing second on him to Three Counties in the 1989 Cheltenham Foxhunters.

 I know you’re a keen hunter and that the government recently announced its intention to ban hunting. What do you think will happen to pointing if this happens?

Trail hunting is well-regulated – for example, we have drones to monitor our activity – so it’s worrying. Without hunting, we won’t get the volunteers. I’ve been Clerk of the Course at Horseheath for 15 years and have a ‘tenancy’, which means I pay for everything and charge the individual hunts. I wouldn’t be able to make it pay without volunteers.
 
John - on Quinz - hunting with the Thurlow

John – on Quinz – hunting with the Thurlow accompanied by his wife, Mel.

There are only three ‘boutique’ meetings in East Anglia that make money – Good Friday at Higham, Grand National day at High Easter and our own meeting on New Year’s Eve, which used to be held at Cottenham and got their best crowds.
I’m usually an optimist but fear pointing will die a death. The people involved are getting older and youngsters are too busy to volunteer.

 

You’re also an owner, enjoying success in recent seasons with the likes of Ragnar Lodbrok and Aramax. Who have you got to run for you this season?

Chadwick galvanises Ragnar Lodbrok to win at Horseheath (Graham Bishop)

 

Alex Chadwick galvanises Ragnar Lodbrok to win at Horseheath (Graham Bishop)
We no longer own Ragnar Lodbrok, but we still have Aramax and have bought Allmankind from Tim Gredley. Last year he ran in the Cheltenham Foxhunters, but we’ll stick to pointing with him and we plan to have some fun with them. There are lots of mates in the Whiskey & Water Partnership – the likes of Caroline and Gerald Bailey, Chris and David Docker, and Alice Vaughan-Jones – and we’ve been lucky so far. We like to have a giggle and have a party!
Connections celebrate after Aramax wins at Horseheath (Graham Bishop)

Connections celebrate after Aramax wins at Horseheath (Graham Bishop)

And who do you expect to ride for you, with Alex Chadwick having turned conditional?
Conal Kavanagh, who won on Ragnar Lodbrok last season and works for James Owen, will ride Aramax and we hope we can get Heidi Palin for Allmankind.

 

What do you enjoy most about pointing?

There are so many people that you know and like. When I first moved to Newmarket, I’d go racing on the July Course in the summer and would meet up with the pointing crowd there – but the atmosphere isn’t the same.

 You’re vice president of the PPORA. What does this involve?

I still represent the PPORA in East Anglia and do things like put up banners and dish out rugs to winners.
In my time, the best thing I’ve done was to get people from the Jockey Club – like Simon Claisse – and the PPSA to come to our meetings and to convince Simon to become our Chair. He’d tell us what he would like the pointing world to do and helped the PPORA get representation on the PPA board. This enabled us to be proactive, because we knew what was going on.

 In recent years, you’ve won both the Michael Connell (PPA) and Jim Mahon (PPORA) awards for services to the sport. How does this make you feel?

Embarrassed first and foremost! There are far more deserving people.

 Who would you give the PPORA award to next season and why?Alan Hill. I don’t think he’s ever been given an award, but he should be. Although – and I’m sure he won’t mind me saying this – he probably gets too many peoples’ backs up!

Alan Hill - deserves an award (Carl Evans)

Alan Hill – deserves an award (Carl Evans)

What would you do if you were in charge of the sport?
I wouldn’t know where to startb !