1) Who are the Howlands? (William Holmes Howland 1886 to 1887, Oliver Aiken Howland 1901 to 1902). Some may try to claim Rob and Doug Ford, given the latter's penchant for assisting his brother.
2) Who is Fred Beavis? I wrote about the hat draw for The Grid.
3) Who is Henry Sherwood? Mayor from 1842 to 1844, Sherwood expired while traveling through Bavaria in 1855. ending a career which also included an eight-week stint as the attorney-general of Canada West.
4) Who is John Shaw? Here's a fuller excerpt of Shaw's remarks on the opening of (Old) City Hall in September 1899 (Shaw served as mayor from 1897 to 1899):
Why people will spend large sums of money on great buildings opens up a wider field of thought. It may, however, be roughly answered that great buildings symbolize a people's deeds and aspirations...It is now the most attractive place in Toronto, and will stand for generations to come, a splendid permanent mark and sign of the strong will, the energy and foresight, the splendid confidence and perfect faith of the citizens of Toronto in the future of their glorious city.5) Who is Ralph Day? He served as mayor from 1938 to 1940, TTC chairman from 1963 to 1972, and operated the Ralph Day Funeral Home.
And here we go with round two. You can answer in the comments section.