In the Canadian federal election of 1965, Sherman was elected to the House of Commons for the riding of Winnipeg South as a Progressive Conservative, defeating LiberalMargaret Konantz by about 3,000 votes. Sherman served as an opposition MP for three years, before losing his seat to high-profile Liberal candidate James Richardson by over 8,000 votes in the federal election of 1968. Following his loss, he wrote a regular column in the Winnipeg Tribune. He was first elected to the Manitoba legislature in the provincial election of 1969, defeating his NDP opponent by more than 1,500 votes in the south-end Winnipeg riding of Fort Garry. The NDP formed a minority government after the election, and Sherman again sat as an opposition member. In the election of 1973, he was narrowly re-elected over Liberal candidate Henry Janzen. Sherman was re-elected by a much greater margin in the election of 1977, in which the Progressive Conservatives won a majority government under Sterling Lyon. On October 24, 1977, Sherman was appointed Minister of Health and Social Development, with responsibility for Corrections and Rehabilitation. In October 1978, the name of his portfolio was changed to Health and Community Services. On November 15, 1979, his title was again changed to "Minister of Health", a position he retained for the remainder of the Lyon government's time in office. Sherman also served as Chairman of the Community Services Committee of cabinet from October 20, 1978 to the resignation of the Lyon government on November 30, 1981. In 1984, Brian Mulroney warned Sherman and other Tories that they must support French language rights of minorities outside Quebec in order to run as Progressive Conservative candidate. Sherman had previously questioned French-language rights in Manitoba. The NDP under Howard Pawley formed a majority in the provincial election of 1981, although Sherman was easily re-elected in his own riding. He resigned his seat to run for the Canadian House of Commons again in the 1984 federal election, but was unsuccessful, losing to Liberal Lloyd Axworthy in the riding of Winnipeg--Fort Garry by just over 2,000 votes. At the time of the election, Sherman listed his profession as "health-care consultant". Sherman did not seek a return to politics since this time. He later served as Vice-Chairman of the Canadian Radio-Television and Telecommunications Commission, and was partly responsible for developing CRTC policy concerning changes in Canadian telecommunications with the growth of the internet and broad-band services. He retired from the position in 1995.