This is a hard one to answer since the term "progressive" can mean many things. In the modern era (20th century forward) the majority of liberal or radical politicians were Democrats. While it's not true that all Democrats are liberal or radical, it is a general trend of Democrats to look forward and toward change while it is a general trend of the Republicans to look backward and toward tradition. Since the notion of "progressive" is rooting the the concept of "progress" (improvement by moving forward and changing) it is logical to assume that most progressives are associated with the Democrats.
Progressive Tax
Most people would call Theodore Roosevelt progressive, but he did not take office until September 14,1901. William McKinley was the President in September 6,1901.
the internet
indifference and hostility
World War I
reign of terror
French Revolution
"progressive" is a rather vague term. One could argue that Theodore Roosevelt and Woodrow Wilson were the two progressive Presidents, which would make Wilson the second one.
World War II.
Cuban Missile Crisis
Eastern Europe-Berlin Airlift
Jacob Riis
" the Bay of Pigs" the Cuban Missile Crisis
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The German invasion of Poland on 1 September 1939
The German invasion of Poland on 1 September 1939