Stories from the Saddle: Milo Herbert
- pporacommittee
- Dec 3
- 7 min read
24-year-old Milo Herbert, from Abergavenny in Monmouthshire, now lives in London, where he works in commercial property for Montagu Evans. However, he returns home most weekends to fuel his passion for horses.
After retiring from the saddle at the end of the 2023/2024 campaign, Milo has returned this year with a couple of big targets… and a big bang, winning on his first two rides back, Grandads Cottage at Garthorpe and Yippee Ki Yay at Larkhill. He talked to Jake Exelby on his way back from a day’s hunting about his background, career and future plans.
Tell me about today and your enjoyment of hunting.
I was out with the United pack, near Bishop’s Castle in Shropshire. My fellow jockey Guy Sankey was there too, and it was wild! We had some hairy moments but got back in one piece. They have an amazing set-up – it’s brilliant country and they have a great huntsman in Jason Wood.
If I don’t go home at the weekend, I try to take a day off during the week – like today – to hunt. I grew up with it – it’s a family thing. My Mum and Dad, Sara and Ben, have always had ponies and hunters. At home, we hunt with the Monmouthshire, where former jockey Charlie Dando is Master of Hounds. He’s seriously hard-working!
What do you think will happen to pointing after a potential hunting ban?
I think there will be a lot fewer point-to-points, and a move to more Club meetings, like the West Mercian Area Races this weekend. I also think it’ll be a struggle to find volunteers – why would you give up your time if it’s not raising money for the hunt? However, I hope that more packs would move into drag hunting and that the hunts and point-to-points can find a way forward.
Talk me through your career in racing so far and how you got into point-to-pointing in the first place?
I started pony racing aged nine and we’ve been affiliated with the Sheppards since then. One day, hunting with the Ledbury, Stan Sheppard told my Mum I needed a faster pony, and persuaded her to buy Dehaven Chipmunk. He then said, ‘You can’t buy the pony without the boots’, and sold us my first racing boots! From then, Matt, Nickie and Stan took us under their wing.
Although I rode fewer than ten winners, I moved on to pointing when I was 16.
Talk me through your first rides and your first win on Butney Rock.
Matt found Butney Rock from Ireland. He’d been good – rated over 130 at one point – but had lost his way. He was a great schoolmaster on the track, although he was difficult at home. We won on our third outing at Lockinge on rock hard ground, which is what he wanted. Unfortunately, he got a leg the next season.
How did your career progress after that?
Next came Ballycahane. Matt and Nickie had worked for Arthur Moore, and he’d regularly recommend horses for Matt under rules or to go pointing. Ballycahane was an absolute giant, and – as a maiden rated over 100 – had a great profile for pointing. We went through the grades together – that’s how you build a rapport with a horse.
Organised Solution and Risk And Roll were next and were both amazing. Risk And Roll was bought from Paul Nicholls. He wasn’t a great jumper, but I’d have been mad to turn down the chance to have a bite of the cherry at Aintree – David Maxwell burst out laughing when I said I was riding him in the Foxhunters!
Yippee Ki Yay is another to have gone through the grades, from Maiden to Hunter Chase. We were looking for a pointer in Ireland, Ed Bailey told me about him, and Harley Dunne convinced me to buy him. He won at Bangor-on-Dee three weeks after he arrived and, once he gets in a fight, not much gets past him.
(I think) all your winners apart from No Dice have been in your family colours. Tell me about him.
No, I won on One Fer Mamma under rules (for Matt at Warwick). No Dice was half-owned by me, and half by Jim Squires and Judith Healey. They’re proper pointing people who do so much for the sport and we’ve never had a cross word.
You ‘retired’ at the end of the 23/24 season and came back this year. Why did you stop in the first place and what made you decide to return?
I really meant to retire. I was moving to London full-time and I’m 6’4” – when I wasn’t riding, my weight went up to 14 stone – so I thought it was a natural time to bring my career to a close, going out on a high after Yippee Ki Yay won at Kelso.
But I had two itches – which were too big not to be scratched: to ride in the Cheltenham Foxhunters, and to get round Aintree. So, I was persuaded to come back to have one last go.
As for the future, I’ll see how it goes. Grandads Cottage is ten, so has got another two seasons in him, and I probably won’t buy another horse. But nothing’s set in stone!
I understand you’re targeting both Foxhunters with Grandads Cottage. Both you and your brother Ivor have ridden in the Aintree version only to unseat at the fifth. Presumably the plan this year is to get over that fence! And then…
Ivor rode Yippee Ki Yay at Aintree last year and exactly the same thing happened – at the same fence – as to me and Risk And Roll. I’d have put my last dollar on them getting round!
Grandads Cottage is more of a Cheltenham horse – he’s got the class for it – and might be taken off his feet over the shorter trip. But he needs to win again to qualify for both races, and it’s easier to qualify for Aintree. He’ll run again in January.
Do you know if your brother Ivor intends to ride again this year?
Yes, he plans to. He was concussed at Aintree and has been out in Zambia on his gap year but is in the process of getting his licence back. He’s got Highstakesplayer, who was second at Cheltenham in May, to ride. He’ll run at Larkhill next week and Ivor hopes to ride him at Aintree – he’s already qualified.
What has been your career highlight?
Winning on what I thought was my last ride. Also, my double at Bangor-on-Dee on Yippee Ki Yay and No Dice. But I beat Ivor by less than two lengths in the Restricted – he hadn’t ridden a winner at that stage, so it was a difficult journey home!
You have a particularly good record in Hunter Chases (four from nine). Why do you think that is?
It’s nothing to do with me – the horses have been well-placed! We don’t normally run our horses in Hunter Chases – apart from the big meetings – unless we think we’ve got a serious chance, and we’ve targeted Novice Hunter Chases with young progressive horses.
Which horse (not one of your own mounts) would you most like to ride?
A Jet Of Our Own, who Nickie trains and Fred Philipson-Stow rides. He’s high-class, jumps and travels, and can run regularly.
Which other jockeys do you admire?
In points, you don’t get much better than Will Biddick and James King. And Bradley Gibbs will never give you an inch. Under rules, Stan Sheppard. Not only is he a hell of a rider, but he’s been so much help to me growing up.
What's your favourite course?
I’ve had my most winners at Chaddesley Corbett, but I’d say Bitterley, even though I’ve not won there. It’s a really good, galloping track
What would you do if you were in charge of the sport?
It’s not original, but why can’t we consolidate resources between tracks with – say – three sets of portable fences being taken round the country and have a centrally-resourced fence building team. That would bring down costs, reduce labour, and be more efficient.
I occasionally go team chasing, which is far more dangerous than pointing! There always seem to be loads of good jockeys with high-class ex-racehorses. They’ve got the adrenalin and buzz for riding over fences, so I think the GB Pointing team should go to team chases and promote our sport, raising awareness. We could also subsidise the RQCs for team-chasing riders.
What are your non-horsey hobbies?
Horses are my number one hobby, but my mates in London aren’t interested, so it’s good to get stuck in with them down my local pubs in Fulham, The Rose and The Boundary.
Is there anything else you’d like to say?
I’ve been incredibly privileged to be in this position and would like to thank Mum and Dad – Mum in particular has been the driving force behind giving Ivor and I our passion. Fingers crossed Ivor gets some of my luck too.
And the Sheppards have been by our side through thick and thin and have made it enjoyable.
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