Teddy Roosevelt enters these episodes not as a subject in his own right but as a periodizing device — the name the guests reach for when they want to mark the moment American government changed direction. The excerpts contain no account of his presidency, his elections, or his policies in office. What they contain is a set of claims about what he started, what he threatened, and what he might still be good for.
The turn toward the federal government
Matt Welch, editor-in-chief of Reason Magazine, dates the change to Roosevelt directly. He describes a feeling in the country that has gone crazy over the last 100 years, “basically beginning with Teddy Roosevelt and kind of spreading ever since then” — a habit of looking to the federal government to solve any and all perceived problems. Welch measures the escalation in decades rather than statutes: the level of government involvement in people’s lives was scandalous in the 20s, and then doubled or tripled over the next 20 years. His illustration of where this ends is the President of the United States discussing steroids in professional baseball in a State of the Union address, and a Department of Agriculture with 100,000 employees. Bob Zadek picks up the figure and turns it into a joke about who should run whom: that is probably more than we have farmers in this country, so the farmers should control the Department of Agriculture rather than the other way around A Libertarian Plan (2010).
Welch frames the whole development as a crossing of what he calls the constitutional membrane, and identifies the expansion of the commerce clause as one of the legal consequences — his example being a Supreme Court ruling that it counts as interstate commerce when someone in Oakland grows a marijuana plant in their backyard for personal consumption. He does not name the case. The remedy he proposes is a cover package of concrete steps to unwind the overhang, and he concedes the work is daunting, though he argues that being out of money at every level of American life tends to clarify people’s minds A Libertarian Plan (2010).
Court packing as Roosevelt’s innovation
Philip Hamburger, a professor of law at Columbia Law School and founder and president of the New Civil Liberties Alliance, makes the most specific claim about Roosevelt in the excerpts. Until 1912, he says, the only court packing had been in response to a Civil War. Roosevelt changed that. Hamburger describes him as a big, intimidating guy who liked to push people around, and says that in defense of administrative power he threatened the courts and the judges — saying he would reconfigure the courts and deprive judicial decisions of their binding effect, and making this a campaign promise. In Hamburger’s account, Roosevelt campaigned on court packing, and this is what introduced court packing as a political element in the 20th and 21st century Philip Hamburger on Court Packing (2021).
Hamburger’s definition of the practice is structural rather than personal: Congress can create new judicial positions so that a president it likes can make the appointments, shifting the court politically. The result, he says, is that the will of Congress and the president dictates results rather than the judgment of the judges. He notes that the court began with six justices because there were three circuits — Northern, Southern, and Middle states — each needing two justices to ride circuit, and that the number rose to nine over the nineteenth century as the country expanded and circuits were added. The closest thing to successful court packing, he says, came around the Civil War, when Congress increased the size of the court under Lincoln and afterward for fear that Southern sympathizers might dominate it. Hamburger’s point about Roosevelt is that the later attempt was a response to mere politics rather than to a civil war, and he warns that court packing now invites civil war rather than following one Philip Hamburger on Court Packing (2021).
Bob Zadek’s framing of the same material is that the Roosevelts, cousins, play an important role in the conversation, and he treats Roosevelt’s dabbling as little-known — a term he defines, in his own case, as meaning he did not know about it. He also puts the number nine in perspective: it is not a magic number, and the number of justices has changed several times in American history, sometimes perhaps for bad reasons Philip Hamburger on Court Packing (2021).
The 17th Amendment and the progressive era
Two episodes tie Roosevelt to the 17th Amendment and to the broader progressive moment of the early twentieth century. Bob Zadek, in conversation with Randall Holcombe, calls the 16th and 17th Amendments sea changes that forever altered the nature of American government and voters’ relationship to it. He places the 17th Amendment in 1913, at the beginning of the second Progressive Era, with Roosevelt as president and populism and power-to-the-people in the air. His account of the amendment’s origin is a minor scandal — a senator who bribed or otherwise used nefarious means to get elected by a state house, which got into the press — after which it was felt that power should be put in the people. Zadek’s argument about the consequence is that the states had been independent co-equal political bodies with representation in Washington, and that after the amendment they became merely agencies of Washington; California, in his formulation, became the California Department of the federal government Randall G. Holcombe on Liberty in Peril (2019).
Holcombe adds a mechanical consequence: before the amendment, the House represented the interests of the people and the Senate represented the interests of the state governments, so any law had to be approved by both. With direct election of senators, senators represent the people too, which lowers the bar for legislation Randall G. Holcombe on Liberty in Peril (2019).
F.H. Buckley, a law professor at George Mason University, gives the 17th Amendment a different genealogy. He says the initiative and referendum movement originated in the West, and that the 17th Amendment was a Western initiative — that the Westerners who are the source of American libertarianism were in favor of direct democracy. He tells right-wingers who puzzle over the amendment that it is important to know where it came from Trumpism After Trump (2022).
Roosevelt as a usable tradition
Buckley’s treatment of Roosevelt is the excerpts’ only sympathetic one, and it is built on a distinction about what Roosevelt opposed. Buckley says that when people talk about the Gilded Age and the money trust, and libertarians reflexively say they are against all that, what should be remembered is that it was not bigness Roosevelt was opposed to. Roosevelt said bigness is natural; the target was the influence of money in politics. Buckley argues this should strike a positive chord with libertarians and Republicans, and that the Republican Party gave away the issue of corruption to the left — which is why, he says, it is called the stupid party. His contemporary version of the issue is the revolving door between Congress and K Street, and politicians making money from insider trading based on legislation they are proposing Trumpism After Trump (2022).
In the same episode Buckley places Roosevelt in a lineage of Republican progressivism alongside Lincoln’s internal policies and Eisenhower, who called himself a progressive and said at one point that the Republican Party must become progressive or it is going to die. Buckley’s book Progressive Conservatism argues that by embracing these Western progressive traditions — economic mobility and direct democracy — the Republican Party can move past what he calls the dead end of modern libertarianism and the woke left Progressive Conservatism with F.H. Buckley (2022).
Across episodes: what changed
The excerpts do not show a developing argument so much as two incompatible uses of the same figure. In the 2010 episode, Welch makes Roosevelt the origin of a hundred-year expansion of federal power, and Zadek frames the remedy as adherence to constitutional limits. In the 2021 episode, Hamburger makes Roosevelt the origin of a different thing — judicial intimidation as a standing political tactic, dated to 1912 and described as a campaign promise. In the 2022 episodes, Buckley reverses the valence without disputing the history: Roosevelt becomes a resource for Republicans rather than an indictment of them, and the 17th Amendment, which Zadek treats as a sea change that reduced states to agencies, becomes a Western and authentically American initiative. The disagreement is not about what Roosevelt did but about whether what he did is the disease or the available cure.
What the sources do not cover
The excerpts contain no biography of Roosevelt: no birth or death, no offices held, no elections, no trust-busting cases, no national parks, no Panama Canal. They name no statute, no Supreme Court case, and no date in his life other than the 1912 campaign Hamburger describes. The commerce clause ruling Welch alludes to is left unnamed, and the 17th Amendment’s ratification is given as 1913 by Zadek without further documentation. Nothing in these episodes describes Roosevelt’s own words at any length, and the one quotation attributed to him — that bigness is natural — is reported by Buckley rather than sourced.