Early Political Career
Greenfield entered public life on a local level soon after moving to his new farm. He was elected to the local school board, where he spent twelve years, including stints as chair, secretary, and treasurer. He also served as Vice President of the Alberta Educational Association, as President of the Westlock Agricultural Society, and as co-founder and President of the Alberta Association of Municipal Districts. Greenfield also was an officer of the province-wide Association of Local Improvement Districts, which advocated for reforms such as a change from a ten-hour to an eight-hour work day, on the grounds that many Local Improvement Districts (LIDs) were having trouble competing with railways for labour. John E. Brownlee later said of Greenfield's involvement in the ALID that it was there "that he was first initiated into the discussion of public subjects, and it became the training ground for his subsequent success."
Provincially, Greenfield was originally a Liberal, but along with many other farmers, began to grow dissatisfied with the Liberal government's treatment of farmers. He became involved with the United Farmers of Alberta, which prior to 1919 was a non-partisan lobby group that eschewed direct involvement in the political process. He was elected to the organization's executive in 1919 and chaired its mass conventions in 1920 and 1921. He followed this by heading an extremely successful membership drive, and was named interim Vice President of the organization upon the sudden death of Percival Baker. Despite this involvement, he did not seek election to the Legislative Assembly of Alberta in the 1921 election, the first in which the UFA ran candidates. When the UFA, which as part of its resistance to old-style politics had contested the election without designating a leader, won 38 of 61 seats, it found itself needing to form a government without knowing who would head it. The logical choice was UFA President Henry Wise Wood. However, Wood had little taste for the minutiae of government, preferring to remain at the head of what he saw as a broader political movement (noting that he would "sooner be President of the UFA than the USA"), and saw party lawyer Brownlee as the best choice. Brownlee, who, like Wood, had not contested the election, felt that the Premier must be a farmer for the aspirations of the UFA's base to be fulfilled. George Hoadley, the only UFA member with previous legislative experience, was considered, but since his previous experience had been as a Conservative—one of the old line parties so disdained by the UFA—he was deemed unacceptable. There was even some speculation that incumbent Liberal Premier Charles Stewart, who had become a member of the UFA before it entered politics directly, would stay on as Premier, but he immediately announced that he would serve only until the UFA selected a leader. A meeting of the UFA caucus in Calgary selected Greenfield, and he took office as Premier on August 13, 1921.
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