Prior to his election to the mayoralty, Dilkens worked as a labour and employment lawyer, having been called to the bar in 2012. He represented Ward 1 on Windsor City Council from 2006 to 2014. He ran largely on a campaign of continuing the policy agenda of outgoing mayor Eddie Francis.
During the 2011 Occupy Movement, an encampment in Windsor supported between 25-50 protestors for two months. In opposition to other city officials, who did not want to cause trouble with the protestors, Dilkens strongly supported forcing the encampment to evacuate, and threatened to "lodge a formal complaint about the protesters not abiding by a bylaw requiring them to get a permit". He stated to CBC news that "they've had their 15 minutes," and he would "like to see them gone, because I don't think their message is coherent."
Stance on Homelessness and Panhandling
As a city councillor, Dilkens attracted media attention and criticism by proposing “no panhandling” zones, describing panhandlers as “accosting, annoying, and interfering.” Local charity and social workers criticized the move as “dehumanizing” and failing to address or understand poverty. In 2019, Mayor Dilkens was asked by local reporters his stance on overdose prevention sites, which had been set up by local social workers to help combat the opioid epidemic. In response, Dilkens, who strongly opposed the sites, said "It's not even worth it" to comment on them. In a separate 2018 interview, Dilkens stated "We don't fund addictions". He was criticized by local community workers for spreading misinformation about the connection between addiction and homelessness. It was suggested that the city invest more in affordable housing and support for local shelters, due to the large backlog at the city-funded homeless shelters.
Urban Sprawl and the "Mega-Hospital" Plan
In 2014, a grassroots group called “Citizens for an Accountable Mega-Hospital Planning Process” was formed to appeal decisions to amalgamate local healthcare into a “Mega-Hospital”, located on the outskirts of the city, a plan supported by Dilkens. CAMPP, claiming thousands of supporters, promoted community involvement in the decision-making process, and “financially, socially and environmentally responsible sound urban planning principles”. CAMPP expressed concerns that the planned hospital would fail to meet the needs of the urban core populations, instead focusing on a plan for urban sprawl that centres new suburban developments. CAMPP also stressed a lack of consultation with Indigenous locals. A long process of deliberations and public appeals by CAMPP ensued over the following years. When the Downtown Windsor BIA contributed to CAMPP's campaign, Dilkens threatened to dissolve the organization. In 2019, Dilkens was criticized for social media comments which appeared to dismiss vandalism perpetrated against one of the CAMPP supporters.
Environmental Issues
In 2015, a petition garnering 12,000 signatures urged Mayor Dilkens to retract municipal approval for a commercial development near the Ojibway Prairie Complex. Local environmental advocates, including an activist group called Save Ojibway, argued that the development would threaten local wildlife and damage the adjacent nature reserve. Dilkens did not respond to the petition, and the municipal board rejected appeals by citizens on the re-zoning of the land. In 2017, Dilkens rejected a related proposal to close Matchette Road, which runs between Ojibway Park and the Ojibway Prairie Provincial Nature Reserve. Citizen groups proposed that closing the road would drastically reduce wildlife deaths from traffic. The council rejected the motion, with Dilkens' support. Dilkens stated: "To move forward with closure of Matchette Road at this time would certainly have put this corporation in a great deal of jeopardy". During the council meeting, security personnel removed several citizens who voiced their objection to a presentation by developer CoCo Paving.
In 2017, Dilkens was criticized for promoting a $3 million dollar project to create a Christmas lights display, in the wake of massive city-wide flooding which caused widespread damage. Critics claimed the city was responsible for the flooding by not properly investing in infrastructure, pressuring the city to re-invest the lights display fund. Dilkens dismissed the critics, stating: “There will be folks who will criticize lots of different decisions”. However, council eventually voted to roll back the budget of the Christmas display to $1.5 million.
Eviction of Windsor Pride
In 2017 Dilkens approved a move to end the tenancy of Windsor Pride, an LGBT+ nonprofit, from a city-owned property. The property was to be converted into parking spaces. The move was criticized by many in the local LGBT+ community. Windsor Pride Director Bob Williams stressed that the organization did not have the time or funds to find an alternative location that was suitable. Dilkens opposed the council's later decision to pay for the moving costs of the organization.
