Documentary Review: 'Chasing the Win'

This horse racing documentary mostly centers on the story of Carl O'Callaghan, a horse trainer who achieved unlikely fame in the horse racing world through his work with Kinsale King. King is a horse owned by Patrick Sheehy, and while training the horse came with immense challenges, O'Callaghan and company persevered to achieve success in the horse racing world. In addition to taking us through O'Callaghan and King's journey throughout the competitive racing world, Chasing the Win also provides information on the inner workings of horse racing and what it takes to find success in the often unpredictable profession.

Written and directed by Chris Ghelfi and Laura Sheehy (the latter being the daughter of Patrick Sheehy), Chasing the Win gives a frank look at the horse racing world. Such an attitude is perfectly appropriate, as the journey the documentary follows throughout this competitive world is not a straightforward one. We hear from O'Callaghan and others about the struggles that come with pursuing success in horse racing, and how even the most skilled individuals in the field have to rely on an element of luck at times. It's a stark but realistic look at a competitive career, which compliments the real-life struggles faced by O'Callaghan, Patrick Sheehy, and others as they embarked on their bumpy journey towards the Breeders Cup with Kinsale King.

The underdog story of King and the hard-working crew behind him is where Chasing the Win is at its best. As the documentary takes us through the challenging parts of the racing world and interviews O'Callaghan and those involved with him, the emotional aspect of Chasing the Win emerges. Going from being homeless and living under a bridge to taking the horse training world by storm, O'Callaghan's life story is incredibly inspirational. His love and passion for horses is equally heartwarming, with this passion being shared among the people O'Callaghan worked with. While O'Callaghan and crew may be vying for victory, they never put that pursuit above King's health and well-being. That dedication to standing by King and taking care of him (win or lose) injects a lot of heart into Chasing the Win, with this and the backstory of O'Callaghan and his colleagues giving the documentary a personal feel. It isn't just about horse racing; it's about a group of unlikely people working together and bonding over their shared love for horses, and sticking together through good times and bad.

It's when the documentary gets into the deeper information of racing, however, that Chasing the Win begins dragging. While the insight the documentary gives to the world of horse racing may be fascinating to those with a vested interest in the topic, it doesn't take away from how disjointedly this information is placed within the film. It often comes across that this information is intruding on O'Callaghan and King's story--the more compelling and consistent part of Chasing the Win. The documentary would've worked better had it balanced out how much of the film focused on O'Callaghan and associates' stories, and how much focused on the ins and outs of horse racing. As is, there are parts of Chasing the Win that slows to a crawl for abrupt information dumps, thus pulling the viewer out of the documentary's heartfelt authenticity.

But while these slogging stretches may take some out of Chasing the Win, the documentary otherwise does well at telling the inspiring story of a man coming from nothing becoming a famous name in the horse training business. The crew surrounding O'Callaghan are similarly compelling, with each having their own passionate reason for getting involved in horse racing and clearly sharing O'Callaghan's love and care for Kinsale King and the other horses in their care. It's an imperfect documentary in terms of structure and pace, but it maintains a great deal of heart that is sure to touch many viewers. And if you yourself have an interest in learning more about horse racing, Chasing the Win's slower bits may be right up your alley.

Score: 6.5 out of 10 nodding horses.