President Theodore Roosevelt, did believe in individual liberty and self-government, but he wasn’t a Libertarian. He was a Progressive and those things aren’t total opposites. As much as Progressives get stereotyped as big government statists today both from an economic welfare state perspective, as well as a big government nanny state perspective who views both economic freedom and personal freedom as dangerous, people like that are Socialists and in some cases even Communists. Not Progressives, because in many cases their views are both regressive, as well as illiberal. Socialists and Communists, tend to view individualism and free choice, as dangerous. Because see those things as freedom to make mistakes that society has to pay for. Which is illiberal and regressive thinking.
Teddy Roosevelt’s rise to political power in America in the 1890s and early 1900s, really the first two decades of the 20th Century, was perfect for his progressive politics. At a time when business monopolies were actually legal. Where children could be required to work and work under harsh conditions and even prevented from going to school. Where if you were rich and were a cooperation, life was very good for you, because you had most if not all the power in the country. There were practically no referees either from government or anywhere else. Which what brought TR on the political scene in American politics because he saw a country where most of the power was very centralized and where most of the country had to struggle because they didn’t have that power.
Teddy Roosevelt wasn’t anti-business, or anti-big business, and even anti-corporate. Unlike Socialist Senator Bernie Sanders who is probably the opposite on all three of those scores. TR just didn’t want business in America to have all the power and get to make the decisions for everyone else. Which is how we got a Progressive Era and why we got the regulatory state in America so American consumers and workers could be protected from predators. Not to run businesses, but to protects consumers and businesses from predatory behavior. From employers who would force their workers to work in unsafe conditions, work overtime with no extra benefit, and sell products to consumers that are unsafe and not properly tested. To give us what we now call the Food and Drug Administration. Without the Progressive Era we don’t get the minimum wage in the 1930s.
Teddy Roosevelt believed in American capitalism, private enterprise, individualism even, but like great sports you need a referee to make sure the teams aren’t trying to physically destroy each other and to enforce the rules of the game. And an insurance system for people who fall down and need help getting back up. Which is how we got the New Deal in the 1930s which was first proposed in the early 1900s, really the first decade of that century. TR was a Progressive because he believed in progress and using government in a limited way to help create that progress, but not to try to run society and run people’s life for them. A progressive, active, limited government, as part of an over free society. Which was Theodore Roosevelt’s progressive vision.