Question

How far can theodore roosevelt be seen as the greatest progressive of them all?

Answer 1

Quite far....although a republican......He went against his party and.... 
Dared tax his fellow rich 
Busted up the riche's business monopolies and corporations. 
Centered his programs on the US middle class/ working class. 
Expanded government greatly (creating the national parks, Panama canal, sanitary commissions and public health care, and greatly increasing the military).