In 2004, Whynott was appointed by the Government of Nova Scotia to be the Co-Chair of the Nova Scotia Youth Advisory Council. He has also served on federal and provincial government committees for Tobacco Control.
In 2005, Whynott was hired by the Nova Scotia NDP Caucus office as a Researcher, where he held the role until being elected to the Nova Scotia House of Assembly in June 2009.
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.
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,[2] becoming the youngest MLA ever elected in Nova Scotia.[3]
Following his victory in the 2009 election, Whynott was named the Government Caucus Whip and served on the legislative committees of Public Accounts, Assembly Matters and was the Chair of the Human Resources Committee. On November 26, 2010, he was named the Chair of the provincial Suburban Priorities Team,[4] and in 2011, he 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 [5]
On January 31, 2012, Whynott officially endorsed NDP leadership candidate Brian Topp for the Leader of the New Democratic Party of Canada.[6]
In the 2013 election, Whynott was defeated by Liberal Stephen Gough in Sackville-Beaver Bank.[7][8][9]