Taylor continued his education, and attended the Winnipeg Collegiate Institute and the Manitoba Provincial Normal School, receiving a First Class Teacher's Certificate.

[2] In 1886, he began training as a law student with James Albert Manning Aikins, later the Lieutenant Governor of Manitoba.

He sought election to the House of Commons of Canada in a by-election for the riding of Winnipeg, held on April 27, 1894.

[4] He campaigned for the Manitoba legislature in the Mountain constituency in the 1910 provincial election, and lost to Liberal candidate James Baird by 282 votes.

Taylor was re-elected for the constituency of St. George in the 1914 provincial election, defeating Liberal Skuli Sigfusson[1] by 101 votes.