Before joining Richmond Chambers, Caspar worked as a volunteer with Haringey Migrant Support Centre, where he assisted with providing guidance on immigration and housing-related issues. Previously, he has worked as a researcher providing country condition reports for the Athens-based NGO, Advocates Abroad, and conducted legal research for Reprieve, examining US drone strikes and international human rights law. He cultivated a particular interest in immigration law whilst working as a Court Marshall for The Supreme Court, which included shadowing a judge on an immigration case concerning the deportation of children of parents with criminal records. Prior to embarking on his legal career, Caspar taught English as a foreign language in Vietnam and worked in a number of roles while travelling in Canada.