Benjamin’s involvement in the Jewish community started in high school at the Tanenbaum Community Hebrew Academy of Toronto and continued during his studies at York University, where he graduated with an Honours BA in Global Political Studies. At York, Benjamin belonged to both Hillel York and the Alpha Epsilon Pi Fraternity. After the October 7 tragedy, Benjamin pivoted to engage with and strengthen the Jewish community through political action.
Through CJPAC, Benjamin was connected with several important political campaigns. He worked as a volunteer and later as the Data Manager for a Conservative nomination campaign in Aurora—Oak Ridges—Richmond Hill. Shortly thereafter, Benjamin joined Don Stewart’s successful Conservative campaign in the Toronto—St. Paul’s by-election and became the Canvass Chair. Most recently, Benjamin served as the Campaign Manager for Robert Kolosowski’s Public School Trustee campaign in Richmond Hill, where a plan to combat antisemitism in public schools, along with a well-executed get-out-the-vote strategy, led to a landslide victory.