In 1997 Guest assisted with Bob Chiarelli's successful campaign against incumbent Peter Clark for Ottawa regional chair.
In the Ottawa municipal election, 2000, Cain ran for the position of mayor of the combined city but came second to Bob Chiarelli.
In 1995, he ran as a Progressive Conservative candidate in the riding of Ottawa West, in the 1995 provincial election, finishing second to Bob Chiarelli by 1,618 votes.
He had been trailing and was a close third behind Bob Chiarelli and popular former city councilor Alex Munter
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Bob Chiarelli: Incumbent mayor, has been mayor of Ottawa since 2001, and was regional chair of the Regional Municipality of Ottawa-Carleton prior.