‘Chasing the Win’ is a Homemade, Heartfelt, but Somewhat Confusing Underdog Story

For those unfamiliar with the world of horse racing, it is usually a pastime of the rich. A high stakes, high risk, high reward business that few can afford to engage with at a competitive level. We have all heard the stories of elderly men who win a couple hundred on the horses at the weekend. The world presented in Chasing the Win could not be further removed from this picture. This is horse racing from the perspective of those with a lot to lose – the trainers and the owners. People who invest millions of dollars in the hope of fame and glory. One truly must have a passion for horses to be so willing to spend their lives searching for that winning horse. 

Chasing the Win starts on a wonderfully high note with some rather homemade titles, introducing Kinsale King (the horse), Carl O’Callaghan (the trainer), and Dr Patrick Sheehy (the owner) rather quickly to make way for King’s unlikely win at the 2010 Dubai Golden Shaheen. In layman’s terms, one of the top horse races in the world. A strong start gives way to a series of setbacks and disappointments, half-heartedly framed by the story of the families who invested their time and money into the horse, as well as the trainer’s rookie success. 

Laura Sheehy, daughter of Dr. Patrick Sheehy, splits the screen time between her father, uncle, and Carl. Each character takes us through their own experiences of the crazy few years they spent with Kinsale King. Hidden beneath the very American story of David and Goliath is an interesting approach to horse racing. Neither Sheehy brother was super wealthy, so they devised a formula which allowed them to invest in cheaper horses for greater returns. Kinsale King was one such horse. Born with issues with his feet, it seemed as though all odds were against him. Until they found a trainer willing to invest the time to understand the horse and turn him into a champion. 

This is the second, and perhaps most significant ‘character’ in the film. Carl O’Callaghan, who is the saviour for the first half of the film, later morphs into a malevolent presence. He is responsible for Kinsale King’s career wins, but he seemed incapable of recreating their success in Dubai. He is an enigmatic figure who lends the documentary some needed joviality and vitality, but there is a weird tension within the film between the dreams and reality. Callaghan is at the heart of this juxtaposition, as he is at the heart of the rise and downward spiral of the horse. 

As a sports documentary, Chasing the Win lacks the polish of Katie or the hard-hitting truths of Icarus, but it works hard to invest the audience in the lives of these horses and the people that believe in them. Even then, it can’t quite decide which story it wants to tell, and what the emotional arc of said film is. Is this a trainer’s journey? Is this the tale of how the Sheehy brothers finally hit a winning formula after a lifetime of buying horses? Is this a story about how brutal and high stakes horse racing can be? 

For those invested in horse racing, this film is an emotional insight into the journey of one specific horse. For the rest of us, it is an overly sentimental sports documentary with no clear structure, where the highs and lows follow no particular order. Furthermore, we are expected to believe in an underdog story which starts with the ultimate win and slowly descends into mediocrity. While not altogether the worst decision for a documentary film, it does suck all the drama and excitement from the film’s journey. One hopes that Kinsale King will make a comeback, will beat the odds, but that hope is never rewarded. Chasing the Win, is all chase and no win. 


by Mia Garfield

Mia Garfield has just finished a degree in Film at Falmouth University. She has just finished her first short ‘Sonder’, keep an eye out for it at festivals in the UK. A big lover of Fantasy, Sci-Fi, and Mythology, her taste is varied. Her favourite films include Howl’s Moving Castle, Memoirs of A Geisha, How to Train Your Dragon, and Big Hero 6. You can find her @miajulianna2864

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