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  • Writer's pictureJo O'Neill

An Interview with Olivia Kennedy - Markle Magnolia Cup Jockey 2023

Olivia Kennedy is an inspiring woman – as was her journey to ride Mr Trick, owned by the Ian Williams Racing Club, in this year’s Magnolia Gold Cup, which fell on the Friday of the week of glossy and glamorous Glorious Goodwood.

The race, five and a half furlongs in distance, began in 2011, aiming to raise money for charities focussed on women. So far it has raised over £2.1 million, with every record broken last year when giving the total of £324,000 to The Brilliant Breakfast. This year, the jockeys raised money for Education Above All’s Educate A Child, which gives all proceeds to Malawian girls at risk of dropping out of their primary school education.

Many women with varying degrees of riding ability are brought together for the race, which has included Olympian Victoria Pendleton, Dido Harding, supermodel Edie Campbell and gold-medallist pentathlete Kate French. In the past, the chosen jockeys have broken many barriers and there's often a lovely story involved, including Khadijah Meliah making history by becoming the first jockey to wear a hijab in a competitive British horserace. She steered Haverland to win in 2019, whilst Thea Gosden-Hood and Candida Crawford dead-heated in 2021. Ashleigh Wicheard, head of travelling to trainer Neil Mulholland, led last year’s riders to take the knee to stand up against racism. Her ultimate goal, to become a positive role model for black women, was empasised when she led all the way to win the race.

Every year, the bespoke colours are created for each individual jockey by fashion designers. The list of past designers holds parallels to a Parisian catwalk: Vivienne Westwood, Amanda Wakely, Mary Katrantzou, Hermes, Kate Moss and Mulberry. This year, the silks were designed by Alice Temperley, incorporating some of her most iconic colourful prints.

Race day memories, especially with son Eion (middle photo)

Being horsey, Olivia, 32, relished the extra challenge of riding racehorses as well as the vigorous fitness regime, whilst juggling life as a single mum. She managed to fit in riding out regularly for dual purpose trainer Ian Williams in Alvechurch, Worcestershire, which isn’t far from her home in Stratford-upon-Avon. She has a seven-year-old son, Eoin, as well as being supported throughout by mum June and boyfriend, Harry. Growing up on the edge of Stratford in Studley, Olivia had three older brothers, Alex, James and Arron, who was an amateur jump jockey.

Olivia is aiming to participate in eventing with her mare, Aphilia, and she owns a cocker spaniel pup called Kid, short for Kid Kennedy. As well as riding in this year’s Markle Magnolia Cup, Olivia is a brand Champion for Equetech Clothing and a member of Cool Ridings, an initiative that increases diversity and representation within equestrianism.

Olivia and Aphilia

Did you have a horsey childhood? I was introduced to horses at the Wacky Warehouse, where my mom worked and organised pony rides. Interestingly, the ponies were from my home village, so my brother and I began taking lessons there. I remember galloping down the field, no hat, no bridle and just pure hope that the horse would stop and I wouldn’t flip over the gate. Life was simpler back then, and I had some big brave pants. Later, I pursued further studies at Moreton Morrell, leading to a foundation degree in Sports Horse Management and Training.

What experience have you had in the racing world? I don't have much experience in the racing world. My brother was an amateur jockey, and he rode for Robin Dickin for a while. However, I was occupied with my Irish dancing competitions, which often clashed timewise, so I couldn't watch him race.

How did the opportunity to ride in the Magnolia Cup arise? Lydia Heywood, the founder of Cool Ridings, was approached by the incredible team at Goodwood, and she recommended me for the race. I feel extremely honoured to have been chosen, and the team at Goodwood has been amazing throughout this experience.

What fitness have you had to do? I made some changes in my fitness routine for the race. I stopped the strength training classes at the gym since it wasn't what I needed. Instead, I focused on mobility and basic strength training related to the fitness test. It was gruelling, and I admire every jockey who passes that fitness test! Due to my previous schedule and my mom's health condition and spinal surgery, I was limited to riding out before and I would go when I could. Now, I ride out every day except one, doing two lots each day. Not only this, but I am training on the Racewood simulator over at Charlie Post’s, which has been so helpful. It's been quite a journey!

What are you hoping to highlight by riding in the race? By participating in this race, my main aims are to highlight the importance of diversity in the sport and to show that despite life's busy nature, one can train and step out of their comfort zone to achieve incredible growth. Moreover, I am dedicated to raising awareness and funds for Education Above All and their vital work in

promoting education for young girls in Malawi. Together, we can make a positive impact and empower these young minds for a better future.

How has the race in the past highlighted diversity within racing? Over the past several years, the race has shown remarkable diversity. Being part of Cool Ridings has truly opened my eyes to the various aspects of diversity within the equestrian world. While we are witnessing an increase in female jockeys, as that used to be sparse, I believe there is still a long way to go in achieving true diversity in the racing world. It's a challenging reality to accept, but my hope is that by showcasing what is possible and opening doors for other ethnic riders, we can provide them with the encouragement they need to reach that start line as well. Together, we can make a positive change in the equestrian community.

In general, how has racing in the past few years become increasingly diverse? When you search for diversity in horse racing on Google, most articles tend to focus on the lack of women riders and the progress made towards equality. However, the real issue lies in the fact that even if efforts are made to get more ethnic riders into racing schools and yards, it doesn't necessarily guarantee that trainers will give them opportunities to ride. The racing world can be harsh, and some owners and trainers may be unwilling to acknowledge their biases, whether conscious or unconscious. Despite this, the work of Riding A Dream Academy is truly amazing, as it encourages the younger generation to start early and make their mark in the sport. My hope is that as these aspiring riders pass their fitness tests and other requirements, more opportunities to ride will become available. I strongly desire to witness more individuals who look like me succeeding in this sport, breaking barriers, and proving that diversity can thrive in horse racing.

Do you have a racing hero? I don't have a racing hero, and I won't Google one to pick an answer but I do admire every jockey for their fitness and dedication to racing. I also have great respect for the horses, as they have a tough job and trust their jockeys completely.

How do you juggle a busy life with being a mum and your equestrianism? Training for the race as a mum has been challenging yet rewarding. The school run and my mum's spinal operation affected my schedule where I could not ride out as much as I wanted, but my incredible support network, especially my boyfriend Harry and my mom, helped me manage. Eoin, my biggest supporter, even wants to do the race with me! Their support means the world to me and I just want to be safe and enjoy myself on the day as Eoin will be there cheering me on.

Explain how you're feeling about riding in the Magnolia Cup: I love challenges, and I'm quite competitive, but when nerves and doubts creep in, my motivation tends to dip. I catch myself asking why I'm doing this and feeling scared, but I quickly remind myself of the purpose and tell myself that I've got this!

I'm more than ready for the race. It's not about winning; it's about participating and raising awareness and funds for the young girls in Malawi. They face far greater challenges, and I should have the strength to complete this race to make their lives a little bit easier.

If there's one thing you want to personally take away from riding in the race then what is it? This race holds multiple valuable lessons. One crucial aspect is supporting and encouraging fellow riders, building them up to gain confidence for the challenge. It's vital to uplift and help women succeed in this sport.

I've learned that training requires a supportive village, and expressing gratitude to the people and horses who aid me along the way is essential. Whether it's a passing comment or a smile, every bit of encouragement is appreciated and makes a difference in my journey. Also, riding racehorses is pretty darn exhausting but it’s incredible!

*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

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