Final answer:
Woodrow Wilson is seen as a more successful progressive because he effectively implemented his New Freedom policies, tackling tariffs, trusts, and high finance, unlike William Howard Taft whose presidency was overshadowed by his mentor Roosevelt and who had a less proactive approach towards progressive reforms.
Step-by-step explanation:
Woodrow Wilson is considered a more successful progressive president than William Howard Taft for a number of reasons. Wilson's progressivism was evident in his New Freedom platform that aimed to tackle what he called the triple wall of privilege: tariffs, trusts, and high finance. Through legislation, he promoted progressive programs that included direct primaries, workers' compensation, and the regulation of railroads and public utilities. In contrast, Taft's leadership suffered due to his estrangement from his predecessor, Theodore Roosevelt, and his less charismatic approach to campaigning and politics.
In the divisive 1912 election, Teddy Roosevelt's third-party challenge split the Republican vote, paving the way for Wilson's victory. Wilson's reforms, backed by his Democratic platform, imposed stricter controls on big businesses and aimed at restoring competition among smaller businesses. Although both Taft and Roosevelt were associated with earlier progressive ideas, Wilson's successful implementation of these concepts and his victory in an election where the public desired progressive change rank him as a more successful progressive leader.
Roosevelt set the stage with his Square Deal, advocating for control of corporations, consumer protection, and conservation of natural resources. But it was Wilson who emerged as a prominent academic-turned-politician, initially as governor of New Jersey and later as President, putting many progressive ideas into action.