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Drake D'Amore has a diverse work experience in various roles such as Part-Time Facility Attendant at Town of Lakeshore, Commentator at Windsor Express, Bartender at Giovanni Caboto Club, Podcaster at The WinCity Sports Podcast, Parks & Rec. Data Clerk at City of Windsor, and held multiple roles including Recreation Clerk, By-Law Enforcement Clerk, Administrative Support Clerk, Customer Service Representative, and Arena Attendant at City of Windsor.