Chutzpah finished third in IRC Division 2 last year, a year after winning the division. Since launching the first of six offshore Chutzpahs in 1986, Bruce Taylor has amassed 27 divisional wins or places. The Caprice 40 holds the race record for yachts under 12.5 metres with a time of 2 days 4 hours 10 minutes and 37 seconds. Taylor, a semi-retired Victorian orthodontist has 44 Hobarts to his name, a record 32 of them alongside son Drew, while navigator Kingsley Piesse has sailed 42 straight. Last year's crew of 10 boast 313 Hobarts between them.

Taylor has come very close to winning the race. His most painful was second Overall to Wild Rose by a little under 39 minutes in 2014. He was fourth in 2007 and fifth in 2013. With previous Chutzpahs, Taylor was second overall in 1990 and sixth in 2001.