Political Thought: T Roosevelt vs Wilson

Two presidents. One Progressive Era dilemma that still won’t go away: do you fix a modern economy by breaking up power or by controlling it with an even stronger federal government? We dig into Theodore Roosevelt and Woodrow Wilson as political thinkers, not just historical characters, and we map how their reform instincts overlap while their constitutional instincts collide. If you’ve ever wondered why people can agree on regulation but fight over “how government should work,” this conversation puts names and arguments to that fight. 

We walk through Roosevelt’s evolution from a fairly conventional Republican successor to McKinley into the New Nationalism champion who argues the federal government must defend the public welfare against special privilege. That leads to big questions about antitrust, corporate mergers, railroads, labor vs capital, and the idea that the presidency should act as a steward with broad discretion. The more Roosevelt trusts national supervision, the more he doubts federalism and the separation of powers. 

Then we turn to Wilson the professor and the New Freedom vision shaped by Louis Brandeis: more antitrust, more suspicion of monopoly, and a decentralizing tone that later shifts once Wilson governs. Along the way, we unpack what “progressive” and “conservative” meant in 1912, why constitutional conservatism could coexist with policy reform, and how debates over courts and substantive due process fueled radical proposals like recalling judicial decisions. We even take a detour into presidential education, Wilson’s PhD, and what academic confidence can do to political negotiation. 

If you like American history, civics, constitutional design, or the 1912 election drama that’s coming next, subscribe, share this with a friend, and leave a review to help more listeners find the show.

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Why Compare Roosevelt And Wilson

SPEAKER_01 0:46

Welcome back to Civics in a year. Today we have Sean Beinberg back with us because I feel like, again, at this point, it's just the Liz and Sean show. But we're talking about one of my most favorite presidents to study, Theodore Roosevelt, and also Woodrow Wilson and their political thoughts and what the difference is with them. So, Dr. Weinberg, when we talk about Teddy Roosevelt, we talk about Woodrow Wilson and their political thoughts, do they have any similarities or are they all differences?

SPEAKER_00 1:19

They're more similar than they're different, is the short version. And particularly after Roosevelt sort of move, either moves, excuse me, Wilson either moves toward or reverts back to a vision that's closer to Roosevelt. So Roosevelt obviously is president first. He inherits the presidency after William McKinley's assassination. And I assume you know this, but Roosevelt was actually put on the ticket as a way to get him out of New York politics. So they thought he would be less dangerous as vice president. So I've seen in some of the historical accounts like various political figures, like, oh God, we're we're doomed. Like, what have we done? So don't get too this is a lesson to party leaders. Don't get too clever by half with your vice presidential picks. A la uh John Tyler, since I know you guys had uh board cash to talk about the sort of slight tactical miscalculation that that one ended up being. So Roosevelt initially

Roosevelt’s Rise And Early Approach

SPEAKER_00 2:16

is, and we talked as we talked about with the populism one, largely a sort of Republican regular. And when he takes over, as what I mean by that is he's not that different than than other Republicans. He's not particularly progressive. He keeps all of McKinley's, he keeps all of McKinley's cabinet, in fact. But he starts getting more and more concerned. Like partly this is he's concerned about a few Supreme Court cases that I think he exaggerates, but partly this is, and it's worth noting too, the New York courts are very aggressive in terms of imposing sort of laissez-faire libertarianism. The federal courts not so much. So a lot of Roosevelt's, I would say, frustrations are he's taking nationally problems that are local to New York in some ways, or especially pronounced in New York. But Roosevelt originally, Roosevelt basically seeks to have much more aggressive federal regulation over industries that he thinks are either particularly dangerous. So Pure Food and Drug Act, for example, is if another one, or connecting back to what we talked about earlier, uh antitrust. So he's aggressive about sort of reinvigorating uh antitrust. But constitutionally, uh, in terms of federal power, what he actually does is mostly pretty cautious while he's president. He sort of runs his mouth about expanding it in a few ways, but his his practice is generally pretty cautious. What happens that really radicalizes him is when he leaves office. As I like to darkly joke with people, some folks say he seemingly loses his mind while he's off on safari. He comes back much, much, much more radical. And we'll talk about another podcast that's more about the personalities of the 1912 election. But for now, and we'll do another one on the presidential power, but for now I want to focus on sort of his political economy that he adopts kind of in 1910, 1912. Probably two most famous speeches for those of you looking for the primary source, uh, either the new nationalism, which is his political economy speech, or Charter of Democracy, which is his speech basically arguing for a much more robust rethinking of constitutional institutions. But effectively, the through line through certainly 1910, 1912,

New Nationalism And Public Welfare

SPEAKER_00 4:32

Roosevelt is he argues that the Civil War was about unjust economic privilege, i.e., slavery, you're working without being paid for it. And so he argues that the federal government must, like it did during the Civil War, destroy special privileges. And so he's very skeptical of corporate power, particularly as we is a through line in this a lot of these years, a lot of these years. Uh, there's a concern about railroads. So he says we may need to nationalize the railroads, but preferably let's regulate them. And as he says, effectively, and this foreshadows the major difference between Wilson and Roosevelt. Roosevelt says that the way out, quote, the way out lies not in attempting to prevent such combinations, meaning consolidated economic power, you know, corporate mergers or something, but in completely controlling them in the interest of the public welfare. And so Roosevelt becomes convinced that the solution to the problems of political economy of the era is not to stop the businesses from getting big, it's to empower the federal government to get even bigger. And then in Roosevelt's mind, Roosevelt will be sort of empowered to adjudicate the public welfare. So he's very much assuming that there is a sort of homogeneous, discernible public welfare, and that he, as the president, will be well versed to discern that. And then, you know, and he wants to then empower the presidency as well. And that's a separate podcast where his constitutional vision of the presidency. But he's increasingly skeptical of the separation of powers. He's increasingly skeptical of federalism. The 1912 Progressive Party platform has sort of, we want to regulate various things by the federal economy, by the federal constitution where we can, but we need to empower the feds if basically this is unconstitutional. So they don't explicitly say tear down federalism, but they're gesturing, uh, they're gesturing toward it. Roosevelt has a real skepticism of uh what he calls gambling in stocks or making money uh instead of from services rendered. And this actually comes from the conservative political theorist Burke. So Roosevelt views himself, again, not as a communist in this sense, but he says, look, there's something fundamentally different between a worker working and like a day trader making money. So this is this is something that comes from Burke. But you see this theme again and again and again in Roosevelt is public welfare. Stuff that doesn't adjudicate uh advance the public welfare needs to be pressed by the government. And so he wants to have the feds adjudicating labor and big business. He will occasionally throw in lines saying, yeah, big business corporations are terrible, but we also need to make sure that we're not supporting like labor radicalism. So he has no stomach for that. And he says he's increasingly impatient with the quote overdivision of government powers. And he nods too, and this is again something will be its own podcast, this idea of the stewardship theory of the presidency, that the president is empowered to act uh for the public welfare. Uh, and he also wants to have primaries with constraints on money and politics. So that's Roosevelt. So, where is Wilson similar? So, part of it's worth noting is Wilson has been a political, he's been an academic. He generally writes like an academic. He's a little better than average academics, I suppose, but still not um, he still writes like a professor and he talks like a professor. So he's been writing for decades about basically wanting to eliminate the separation of powers. And originally he wants a weak president, eventually and a strong Congress. Eventually he decides that Congress basically can't be fixed and can't be dealt with. And so he wants to flip it and empower the presidency and the bureaucracy, uh, which we're gonna be in the president today. The main so they both are skeptical of the separation of powers. That's a commonality. Wilson, however, uh adopts a vision that's

Wilson’s New Freedom Meets Reality

SPEAKER_00 8:26

called the new freedom as opposed to Roosevelt's new nationalism. And this is very heavily influenced by Lewis Brandeis, which is a name I assume you're familiar with. He's a future Supreme Court justice. Uh Brandeis is interestingly an old William Howard Taft kind of supporter. So Brandeis is very much antitrust and anti-monopoly. Uh, so he is in some sense a kind of new Jacksonian, right? He wants to see power broken up and divided. He's big into federalism. Wilson picks up Brandeis and sort of adopts his vision. Scholars debate to what extent Wilson actually had been committed to this kind of decentralized federalism vision versus realizing that he needed to do that to win the Democratic Party primary, right? So that's above my pay grade. Did Wilson flip? Was he lying the whole time? But very clearly, Wilson in 1906-1908 sounds very states rights-y. 1912, he sounds moderately states rights-y. When he becomes president, he moves from that. So originally the new freedom is supposed to be antitrust, anti-monopoly, tariff reform, reduced tariffs, and banking regulation. And as he says, it's less about the distribution of powers of the government, which is Roosevelt's concern. He wants to shuffle. Is this feder state? Is this president congress? And Wilson says it's more about societal forces. That we now have a world where scale means the employer doesn't understand the worker, and scale means employers are able to push politics. It push influence politics in ways that seem that seem unsettling. So the core vision is that Wilson wants to use, at least in 1912, the power of the federal government to break institutions up. Roosevelt wants to use the power of the federal government to be a steward and a garden of basically big institutions. Now, Wilson once he's president very famously, he does the tariff reform, which is mostly pushed by a member of the Senate, Oscar Underwood, but largely ends up adopting many of Roosevelt's policies, which infuriates Roosevelt because most of Roosevelt's house intellectuals all jump ship and say why they like Wilson. So that's a sort of sort of awkward, sort of awkward thing there. But so at the time, if you look at the newspapers, they will regard Wilson as like the moderate conservative. Roosevelt is the radical, and Taft is just sort of out there doing his own thing. I don't think it's fair to say Wilson is an actual conservative in 1912. He looks like it by comparison to Roosevelt's. But again, constitutionally, Taft is the conservative, even though policy-wise, again, all three of them are moderate to progress or moderate to radical progressives in some, not radical, but moderately radical progressives. But their real difference is constitutionalism. And that'll be its own separate podcast.

SPEAKER_01 11:27

When you say the term conservative, is that does that have the same meaning that it would today?

SPEAKER_00 11:33

Broadly speaking, well, broadly speaking, for most, Roosevelt wants to say that he is the conservative because he says, I am trying to undo basically aggressive corporate power. And so there is a wing of progressives. And so this there's a long debate. In fact, my colleague Aaron Kusher and I had a peer-reviewed article recently where they basically insisted that we add a long paragraph on like, what is a progressive? What is a conservative? What do the progressives mean? Right. And so I could bore you to death talking about that. But broadly speaking, it has a similar meaning. But the one thing that's striking is that today policy and constitutional views are collapsed.

What Progressive And Conservative Meant

SPEAKER_00 12:14

And at the time, I would say that most folks are constitutional conservatives, even if they are policy progressives. So they say we should interpret the constitution. They don't use the word originalist, but basically, like as the founders would have understood it. But different political economy means that we can regulate things differently. So if you want to ship something across state lines, an originalist would say the feds could do this. So if you want to be a big multi-state corporation, you by definition are effectively consenting to more federal power, even if it's the same understanding of the Constitution. And so that split, it's a great question. And that split ends up largely explaining why Roosevelt's cronies, which we'll talk about in a future podcast, at least the fun parts, all bail on him because they say, look, we're policy progressives, we like the Pure Fruit and Drug Act, we like, you know, the Man Elkins Act, we like the various federal regulations that are legitimately about dealing with interstate commerce. And these are good, but this doesn't mean you can regulate local governments, local policies, and this doesn't mean we want to destroy the separation of powers. And it doesn't mean we want to play around with some of the most radical forms of direct democracy that Roosevelt plays with. I mean, in that the Charter of Democracy speech, he suggests that judicial opinions should be able to be recalled. Now, originally he's talking about that as a state issue, but clearly it's a stalking horse for feds. But he basically wants to say some people are mad at the courts for uh overly expanding the due process clause. We've talked about that substantive due process, and they're sort of reading in economic views. And so the position that like Oliver Wendell Holmes and others take would be let's constrain it to basically say due process is about process, not about us imposing our economic views. So that's the kind of moderate corrective. Roosevelt wants to have voters just say, like, nope, we don't like that opinion thumbs down, which would be which as freaks Taft out not unreasonably because Taft says, What do you do if they just strike it down, but not the precedent or the reasoning? And now we have sort of conflicting, conflict conflicting lines of doctrine. Like, this isn't how courts work. See Federalist 78, basically, is Taft's take here. So yeah, progressive and conservative, at least on the constitutional grounds, broadly mean the same thing. And to the extent that it's more or less regulation, it has sort of a similar continuity. But again, people, even folks who we would code as sort of moderate conservatives, recognize they need to make more regulations in the wake of this economy. So like Coolidge actually looks when he's in state government, foreshadowing a few podcasts from now, Coolidge looks like a moderate progressive in state government and then looks more conservative in when he's at federal office. William Borah, who will come up in the next podcast as a senator, is the same, kind of the same thing.

SPEAKER_01 15:08

And you talked about Woodrow Wilson being a professor. Woodrow Wilson to this day is the only president who had a PhD. And his was in history and political science. So it and maybe this is an opinion question, but do you think that, you know, him having a PhD and him having, you know, I looked up his dissertation title. His dissertation was Congressional Government, a study in American Politics. Yes. Do you think that that, you know, having that kind of an educational background influenced him? But then once he got into the presidency, you know, things kind of changed because when we look at him and Roosevelt, I think, I mean, they're two very different people.

The PhD President And Leadership

SPEAKER_01 15:55

And educationally, again, having I mean, president, there is no in the constitution, there is no educational, you know, requirements. But to have a PhD and to be, you know, a president of a university, he was trying to get a law degree, like he was doing all of these things. How do you think that influenced him in his presidency?

SPEAKER_00 16:17

Probably for the worst, but is the glimpse speaking as somebody in that profession. Uh I I would actually, I would, I would actually push back on the question a little bit. Okay. So he is the only one that has a PhD. He is not the only sort of academic or scholar. Since he's getting play now because of the, what is it, Death by Lightning? There's like a Netflix series about Garfield. Garfield is a wildly, I mean, one of the real tragedies in history is Garfield getting assassinated. Not just because it Garfield is basically a brilliant academic. Uh, he's a president of a college at one point. And he does, you you can you can read up just like how intellectually impressive it was. He like created new proofs of geometry. He is, he was, I would argue, much more brilliant than Wilson, if we want to measure on that metric. Interesting. I I would also argue that Roosevelt doesn't have a PhD, but Roosevelt is somebody who like on the side writes history books. Like he knows a lot about history. So they're both they're both actually pretty scholarly in some sense. To to your point about Wilson specifically with the graduate degree, I would actually argue that in some sense it makes him less effective as a president, partly because he's very so he studies at Johns Hopkins. Hopkins is mostly staffed by people who had gone and trained in Germany. And so that's where he kind of picks up a lot of his views about kind of teleological progress, like Hegelian, and this is all sounding super boring, and it is, but he basically picks up this vision that like history is moving in a singular direction and it can be directed sort of by by great people. And similarly, that there's a sort of skepticism he picks up of uh American institutions. And so that that I think we'll connect for the one we talk about the bureaucracy and executive power. But Wilson's academic scholarship is not about how much he loves the constitutional institutions. It's very much picking up this sort of kind of proto-deconstructionist stuff from the Germans. And so that's why his scholarship is very skeptical of the separation of powers. And then when he's president, he very much is skeptical of separation of powers. So I don't think it's an issue that he gets elected any changes because that now like the boring professor suddenly has to confront reality. He never really confronts reality in some ways, which is partly why he has so disastrous in foreshadowing, like trying to negotiate the Treaty of Versailles stuff, because he has a sort of acad a pompous academic's take on like, I'm smarter, I know better, I don't need to negotiate with you people. So I think that makes him in some ways less, less effective. He's able to push through things where he has broader consensus stuff, but a lot of his things don't go through or they're sort of very quickly yanked out. So, no, I am not advocating PhDs as an essential uh qualification for for uh academia uh for uh for the the presidency. There are political figures who have been scholars who I think are pretty great. I'm not gonna rattle them off here, but but again, it's also worth noting just the education system back then, folks that just had a BA had a better understanding of the Federalist Papers than many of my colleagues in grad school exhibited. You know, Coolidge can name drop the Federalist Papers with comfort and ease in a way that folks in grad school today probably cannot. I mean, you've looked at you've looked at those old like take the civic, take the like exit interview, the exit test for like seventh grade folks before and like, damn, this is PhD level work.

SPEAKER_01 20:17

It is. And I I I love that we got off on this tangent because now like I'm looking our friends at you know UVA's Miller Center have something, you know, James Garfield, the education president. So I guess that's my my next rabbit hole to go down. Dr. Beinberg, thank you. Thank you for also going on our little side quests on you know education and presidents, because again, I just think these things are interesting. I'm really looking forward to our next podcast. We're talking about the election of 1912. So all of these figures, you know, we've talked about, we're going to really get into some historical drama, which we all know is my favorite. So, Professor Beinberg, thank you.