Chasing the Win documentary review


★★★★

Directors: #ChrisGhelfi, #LauraSheehy

Starring: #CarlOCallaghan, #PatrickSheehy, #DenisSheehy

Documentary Film Review by: #ChrisOlson


Chasing the Win documentary

Known as the Sport of Kings, horse racing is a long established culture of contrast. On the one side is the aristocratic traditions and elegance (think of the Queen and all those silly hats at Ascot) and on the other is the mud, sweat, and tears of training animals to run really bloody fast whilst audiences bet on the outcome (most often losing). Documentary film, Chasing the Win, directed by Chris Ghelfi and Laura Sheehy, follows a true underdog story where this contrast is even more apparent and at times crushing.


Carl O’Callaghan was once homeless living under a bridge. After trying his luck as a musician and then as a horse trainer, the man (some years later) found himself winning one of the most prestigious horse racing events of the year - the Dubai Golden Shaheen. Along with the horse’s clinically minded owner Patrick Sheehy, O’Callaghan quickly rose to stardom on the back of Kinsale King’s burst into racing royalty. However, the journey was just getting started for this unlikely trio, who had to battle injury, money, and logistics in order to keep a foot in the race.


An allegory for the American Dream, Chasing the Win contains some fantastic storytelling aspects. There is the rags to riches story of Carl, the wounded but born to win Kinsale, and the daring but under-prepared business acumen of Sheehy. Following their journey across the globe, through race after race and countless obstacles is utterly compelling but also laden with pathos. Audiences won’t be able to help themselves from getting completely invested in seeing Kinsale become victorious, justifying the great lengths that his owner and trainer go to.


Far from being an impartial piece (Laura Sheehy is Patrick’s daughter I believe) the documentary becomes more like a diary of the family business, but is presented with warts and all. The realities of the industry are laid bare and Sheehy in particular is openly honest about the tough choices that are needed in order for a small operation to compete in the big leagues. When dealing with wins of $1M and up, and horses being sold for massive amounts too, this is not some archaic equestrian pastime - it’s big business.


Riveting and enlightening, with huge amounts of storytelling prowess, the #filmmakers capture the poignancy of horse racing through their own dramatic journey through it. A powerful parable of our own search for success which can often be only one outcome out of a million other ways to lose.

Watch the official movie trailer below.