Cheeseman's documented background is in Toronto, the largest city in Ontario, where he completed his university studies and built his legal career.
Ontario's legal profession has long been self-governing. The Law Society, founded in 1797 as the Law Society of Upper Canada, was the body that controlled entry to the profession through legal education until 1957, and it remains the licensing body for lawyers and paralegals in the province.
Cheeseman earned a Bachelor of Arts with honours from York University in 1980 and a Master of Environmental Studies from the same university in 1984. York was founded in 1959 in response to the rapid growth of Toronto's metropolitan area, with support from the North Toronto YMCA, which was interested in promoting adult education. The university moved to its Glendon campus in 1961 and opened its main campus in 1965, and its faculties today include environmental studies. His master's degree was in environmental studies, with an emphasis on urban planning and planning law.
He received a Bachelor of Laws from Osgoode Hall in 1984. The Law Society established the law school in 1889, and it became the second oldest common law school in Canada. The school moved to York University in 1968, becoming part of that university's structure.
Cheeseman was admitted to the Ontario bar in 1986. The Law Society, which was founded in 1797 and renamed the Law Society of Ontario in 2018, remains the self-governing body that regulates lawyers in the province.
Cheeseman's principal documented firm affiliation was with Weir & Foulds, where he worked as a partner. The firm was founded in Toronto in 1860 and now operates as WeirFoulds LLP. Its history is tied to Toronto's growth as the industrial center of Ontario in the late nineteenth century, and its core practice areas include litigation, corporate, property, and government law.
Cheeseman's legal practice concentrated on planning and municipal law. He has appeared on behalf of clients before the Ontario Municipal Board, a provincial tribunal that heard land-use and planning appeals, and before the Niagara Escarpment Commission, the body that administers planning for the Niagara Escarpment. His matters have included shopping centre development, official plans, zoning by-laws, plans of subdivision, and Aggregate Act issues. He also appears before committees of adjustment, land division committees, and municipal councils across Ontario.
Cheeseman also practices with Municipal Law Chambers in Toronto, where his work includes real estate development and environmental law. He has defended individuals and corporations charged under local by-laws, the Ontario Building Code, and the Niagara Escarpment Planning and Development Act. He has presented papers at seminars for the Law Society of Upper Canada and the Canadian Bar Association, a voluntary professional organization formed in 1896 whose Ontario branch serves lawyers in the province.
Cheeseman's municipal law practice connected him with the Canadian Bar Association's sections, which provide members with information on specific areas of law. The Municipal Law Section addresses the planning and municipal field in which he practiced, and his executive role within it linked his professional work with the association's provincial activities in Ontario.
