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An Interview with Jamie Insole, Assistant Trainer to Charlie Hills

Not many people have the racing pedigree with as much black type in it as Jamie Insole! Jamie’s family includes successful jockeys and trainers, so it’s only natural that he is paving his own way through the racing world. Jamie, 26, has worked over both codes; having started off in National Hunt as a jockey, he latterly has risen up through the ranks in hope of, in the future, becoming a trainer. He is currently working as an Assistant Trainer in a Flat yard. He looked after Smad Place at Alan King’s, a superb chaser who won 2015 Hennessy Gold Cup, 2016 Cotswold Chase and the 2017 Old Roan Chase. Since concentrating on the Flat, Jamie has been associated with top-class Flat-performer Equilateral, who took him to Dubai.

Originally from Billericay, Essex Jamie now resides in Lambourn, Berkshire.



Do you have any family connections to racing?

My grandfather, Vivian Kennedy, was an Apprentice Jockey to Tommy Burns in Ireland and won the Irish Cesarewitch on Bigaroon in 1970. He then started training in 1983 and won the Kerry National in 1986 with Flute Player. My grandmother, Kathleen Kennedy, designs and produces most of the racing colours in Ireland. Three of my uncles were all jockeys. Vivian Kennedy Jnr was Conditional to Fred Winter before he was killed in a fall at Huntington. Niall Kennedy, who rode as an Amateur, now runs a successful Equine laundrette servicing most of the racing yards on the Curragh in Ireland. William Kennedy rides as a professional jump jockey now and was Champion Conditional. My mother also worked for Dermot Weld before she moved to the UK.


Did you have horsey childhood?

I grew up in Essex, away from our family racing yard in Ireland, so I wasn’t around horses every day.

When we visited our family in Ireland though I would sit on a pony from an early age and I would be out on the gallops with my grandfather watching the horses. It wasn’t until I was around 6 years old that I started having riding lessons and a few years later I would spend my summer Holidays in Ireland at Pony Camp.


How did you get into racing?

When I was about fifteen, I went to Alex Hales Racing for a few weeks during the summer holidays. This is where I learned the basics in caring for racehorses and also got my first taste of exercising horses up the gallops. I returned to Alex’s a couple more times. I then spent six weeks during my summer holidays at Paul Webber’s when I was 16 and 17. I learnt so much there, from riding work to schooling and it gave me valuable experience. Over the years, I also used to spend time with my uncle William who would take me out with him racing and into the yards to ride out. At the age of 16, I rode in the Greatwood Charity race for Paul Webber at the Cheltenham November meeting. I then went on to ride in the Cancer Research Charity race at the Cheltenham Festival for Gordon Elliot. My parents told me to stay in school to complete my A-Levels which I did. However, as soon as I passed my driving test, I would miss the first two periods of classes, at least once a week, to drive up to Newmarket to ride out for John Berry and Neil King before rushing back to Sixth Form.


Which trainers have you worked for and in which roles?

My first full time job in racing was for Nigel Twiston-Davies at the age of 18. I held my Amateur licence while I was there and had a few rides ‘pointing. I then moved to Alan King’s and stayed there for five seasons. I was mainly riding ‘pointing to start with. In my second season at Alan’s, I turned Conditional and, on my first ride, I broke my jaw and missed half the season. I spent another season as Conditional before turning back to an Amateur and taking up the role of Pupil Assistant Trainer to Alan for two seasons. I then moved to Charlie Hills in Lambourn in February 2018 as a Pupil Assistant and became an Assistant Trainer at the start of 2019.


Jamie with Khaadem


Why did you make the switch from National Hunt to Flat?!

I had spent the majority of my career in National Hunt racing and after spending five seasons with Alan King and thinking about my future of hopefully becoming a Trainer, I thought it was best to get some valuable experience in a large, classic and winning Flat yard.


Please describe your current role as Assistant Trainer:

As Assistant Trainer to Charles Hills, it’s my job to organise the staff and horses in the yard. I normally ride one or two lots each day before helping Charlie to organise the rest of the lots and watch them on the gallops. I check legs in the evening and liaise with the Barn Leaders for any medical concerns that they might have. I also organise the riding out board each evening and sort out other office work such as entries, staff holidays as well as owners’ and vets’ reports. When Charlie is away, it’s my responsibility to take charge of the yard alongside our other Assistant, Nicola. I also attend races to represent the yard and to look after owners.


What was the best advice you have ever been given?

To always remain grounded and to keep your head down and work hard.


Jamie with the successful Smad Place

Photo Credit: Karl Macwilliam


What is the best advice you can give?

As with any sport, it requires a lot of dedication and commitment and if you show these traits, you’ll be sure to have a bright future.


Ideally, what does your future hold/what are your dreams?

I would love to start training one day. The past few years have been all about gaining the knowledge for me to pursue this. I have been lucky enough to travel to Dubai and America this year to see different training methods and over the next few years, I hope to learn as much as I can about training whilst also building some valuable contacts which will help me to get started.


What is your favourite racecourse?

My favourite has to be Cheltenham. I’ve been going to Cheltenham since I was a little boy and have many fond memories of watching my uncle William riding there. You can’t beat the atmosphere at the festival and its really something special.


Please list a few of your favourite racehorses:

Smad Place, McCabe Creek, Khaadem and Equilateral.


Jamie with a winning Equilateral in Dubai


What have been your best days racing?

It’s a hard choice between Smad Place winning the Hennessy Gold cup or Equilateral winning the Dubai Dash. When Smad Place won the Hennessy, it was just magical. We had recently lost a friend who worked in the yard and it brought everyone together. We certainly celebrated!

I was sent to Dubai for the winter to ride and train Equilateral and when he won the Dubai Dash, a first Dubai Carnival winner for Charlie, it was brilliant. I felt a great satisfaction seeing him run away with James Doyle nearly all the way to the finish line.


What is your favourite holiday destination?

I headed to the Maldives recently and it became my new favourite holiday destination.


What is your favourite meal?

I love duck and fresh seafood.


What is your favourite drink?

Red wine



What are your other hobbies?

During lockdown, I took up road cycling and I even built my own bike. I’ve managed a few 100km rides over the summer and next May I’m planning to cycle from London to Paris in 24 hours. I also play Golf but like playing any sport really, including cricket during the summer.

I also have my own horse, McCabe Creek. He gave me my first winner as a Conditional for Alan King, and was part of a five-timer that day (Ziga Boy, Annacotty, Yanworth and Smad Place). I have evented and hunted him.

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