[2][3] He represents the electoral district of Stephenville-Port au Port as a member of the Newfoundland and Labrador Progressive Conservative Party.

On January 17, 2023, Wakeham announced he would be a candidate in the 2023 provincial PC leadership election.

[5] In 2018, Wakeham ran for the leadership of the Progressive Conservative Party of Newfoundland and Labrador, but was defeated by St. John's lawyer Ches Crosbie.

The final tally was Crosbie with 2,298.92 and Wakeham with 1,701.08 points respectively.

[6][7][8] Prior to entering politics, Wakeham was the CEO of Labrador-Grenfell Health Authority, was a franchisee of many KFC restaurants[9][10] and has served as the President of both the Newfoundland and Labrador Basketball Association and Basketball Canada.