When he was first inaugurated as a Montreal city councillor in 2013, he was quoted as saying, "I grew up in a village where there was a strong tradition of democracy, so for me this is a very solemn ceremony.
Project Montréal became the official opposition on city council after the election, and Caldwell was chosen in early 2014 as his party's critic for citizen services and Space for Life.
He initially received this position on an interim basis, filling in for Peter McQueen, who was then seeking election to the House of Commons of Canada.
[9] During his first term on council, Caldwell fought for the Montreal Botanical Gardens to revert to its previous policy of allowing free access outside of operating hours,[10] promoted self-service carsharing in Mercier–Hochelaga-Maisonneuve,[11] took part in the preparation of the borough's éco-quartier environmental plan,[12] and sought to protect natural areas in Pierrefonds-Ouest against a proposed housing development scheme.
Following the election, new mayor Valérie Plante appointed Caldwell to her executive committee with responsibility for urban planning, transit, and Montreal's office of public consultation.