A tavern owner with ties to the Tory Family Compact, his brother, Henry Sherwood was Mayor of Toronto and then Premier of Canada West in the 1840s.
According to Conyngham Crawford Taylor, Samuel Sherwood was “a quiet, good-natured man, who did not insist on any strict regulations as to the dress or discipline of the men.
[3] Sherwood was appointed chief constable despite the fact that a provincial inquiry had implicated him in the 1841 election riot that followed his brother's electoral defeat that year.
Sherwood had allegedly organized an armed gang inside the Coleraine Tavern which opened fire upon participants in the rival candidate's victory parade.
[4] In 1858, Sherwood let the prime suspect in the robbery of the Bank of Upper Canada go free prompting the mayor, William Henry Boulton, to order an inquiry.