[2] In 2003, Grimes ran as a municipal councillor in Ward 6 Etobicoke-Lakeshore to replace Irene Jones who left the seat to run in the provincial election.

"[4][5] Although Grimes was generally opposed to initiatives supported by Mayor David Miller, he became a key player in getting the land transfer tax passed in 2007.

According to a Toronto Star newspaper story, dated July 5, 2016,[8] Commissioner Jepson found that Councillor Grimes had "breached council rules when he took part in 'improper' dealings with two different developers".

The Star also reported that "Grimes revised an agreement with Davies Smith Developments that resulted in $100,000 less in cash benefits than originally agreed to for one of his ward communities".

Further, the story goes on to state that "The integrity commissioner also found that Grimes improperly used the influence of his office when he appeared in a promotional video for another developer, Empire Communities, in 2014".

Then-councillor Di Ciano and Grimes hired the firm of strategist Kinsella, to compile a "research" dossier on him and political foes.