First past the post is not the only winner. Travelling in Australia with her family for a wedding, English journalism student Zaniya Fergusson fears six days in the small southern city of Hobart will leave her bored. A chance encounter in the hotel breakfast room with recent widow Helen O'Shaughnessy changes her mindset. Lucky O'Shaughnessy was known as the world's worst jockey, falling in all forty-five jumping races he rode in. A figure of infamy and ridicule throughout his career, he'd been long forgotten until a newspaper article after his passing bestowed the title of Hobart's Greatest Loser upon him. The Fergussons experience the wonders of Hobart and its surrounds. The culture of MONA, the history of Port Arthur, the natural wonders of the Tasman Peninsula, the restaurants of North Hobart, the nightlife of Battery Point, the tranquillity of Bruny Island and the beauty of Cradle Mountain. Against these diverse experiences, they learn the fuller picture of the man Lucky had been. Can Zaniya convert Lucky's legacy from loser to hero?