Whynott grew up in Lower Sackville and attended Sackville High School. Throughout his years before become a MLA, Whynott was involved with many community groups and organizations including the Knox United Church Council in Lower Sackville, Big Brothers Big Sisters, the Dal/IWK Adolescent Mental Health Committee and the Sherbrooke Lake United Church Camp. Whynott also spent time working with the Cobequid Community Health Board in conjunction with the Youth at Risk Network to establish a Youth at Risk Centre for the Cobequid Health Region. In 2006, Whynott was selected for an all-party group to travel to the Middle East in conjunction with the Canada Israel Committee to learn, first hand, about the conflict. In 2009, Whynott was chosen as one of the Chronicle Herald's Top 20 20-Something's for his work in the Sackville community. He followed this honor up with attending an international conference in Trinidad and Tobago and he has represented Canada at the United Nations, speaking at the UN's World Programme of Action for Youth.
As a first-time candidate, Whynott finished second in the Hammonds Plains-Upper Sackville riding in the 2006 election. Whynott won 36.05% of the vote, 5.97% and 516 votes behind Conservative incumbent and Cabinet Minister, Barry Barnet.
2009 election
Whynott ran for the NDP for the second time in the 2009 election campaign. Building off his gains in his 2006 election campaign, Whynott was elected in Hammonds Plains-Upper Sackville, defeating Barnet, Liberal candidate, Patrick Doyle, and Green candidate Shawn Redmond. On June 9, 2009, Whynott took the riding with more votes than the Liberal and Conservative candidates combined, becoming the youngest MLA ever elected in Nova Scotia.
Member of the Legislative Assembly
Following his victory in the 2009 election, Whynott was named the Government Caucus Whip and serves on the legislative committees of Public Accounts, Assembly Matters and is the Chair of the Human Resources Committee. On November 26, 2010, he was named the Chair of the provincial Suburban Priorities Team, and in 2011, was chosen as a member of the provincial Cyberbullying Task Force where he facilitated focus groups across the province on the challenges and possible solutions to cyber bullying On January 31, 2012, Whynott officially endorsed NDP leadership candidate Brian Topp for the Leader of the New Democratic Party of Canada. In the 2013 election, Whynott was defeated by Liberal Stephen Gough in Sackville-Beaver Bank.