Michael Diamond

Founding Principal

Michael Diamond is a campaign strategist and political commentator who has served as a senior advisor to politicians and political parties across Canada.

Having worked on over twenty political campaigns in five provinces, Michael is a specialist in grassroots engagement who has helped leverage the power of stakeholders for well-known clients in Canada, the US, and Australia.

Among his more noteworthy accomplishments, Michael served as the Director of Operations to Toronto Mayor Rob Ford in 2010, when he co-chaired the “get out the vote” effort, Campaign Manager for Doug Ford's successful 2018 Progressive Conservative Party leadership bid (the highest membership participation race in the party's history), Campaign Director for the Progressive Conservative Party of Ontario’s 2018 general election campaign, and as a senior official in the 2022 PC re-election campaign. 

Michael was a senior advisor to Heather Stefanson’s leadership campaign for the Progressive Conservative Party of Manitoba and served on Premier Stefanson’s transition team following her victory in 2021. 

In addition to his government relations work, Michael is a regular contributor to Canadian media, where he offers his insights on politics and culture. From 2019-2021 Michael served as Chairman of the Ontario Trillium Foundation, Canada’s largest granting organization.

The Upstream Team.

Christina Mitas
Vice President
Chris Chapin
Managing Principal