Alexander Hamilton appears in the excerpts of The Bob Zadek Show as a recurring historical reference rather than as the subject of a dedicated episode. Guests and host invoke him in discussions of insider trading, political scandal, judicial power, federalism, and tax enforcement. The excerpts attribute to him the first act of insider trading in American history, the first sexual scandal of the young republic, the description of the Supreme Court as the “least dangerous branch,” a unitary view of sovereignty at the Framers’ Convention, and the federal response to the Whiskey Tax rebellion.
The first insider trader
In the 2009 episode on insider trading, Bob Zadek poses a history question to Don Boudreaux, professor of economics at George Mason University: who was the first insider trader in American history? Boudreaux guesses George Washington, then John Winthrop; Zadek hints that the man’s picture is on the $10 bill, and Boudreaux answers Alexander Hamilton. Zadek then tells the story: Hamilton was George Washington’s Secretary of the Treasury and the first to hold that office, and Zadek describes him as a big-government kind of guy. According to Zadek, the colonies financed the American Revolution by issuing paper money called Continentals, which the states were obligated on; after the war the states held debt they could not repay, and the currency traded for pennies on the dollar. Hamilton’s plan was for the federal government to buy up, honor and pay off all the state debt. Zadek describes opposition from the southern states and a dinner among Jefferson, Madison and Hamilton called the Great Dinner Bargain, in which the northern states agreed to let the nation’s capital be in the south in exchange for the southerners allowing Hamilton to buy up the script. Hamilton then told his buddies to buy Continentals for pennies on the dollar because the federal government was going to guarantee them; his friends in the northeast bought up the script, and when Hamilton announced the guarantee they cashed in at 100 cents on the dollar. Zadek calls Hamilton the first insider trader in American history, whose picture is on the $10 bill. Boudreaux adds that Hamilton’s statue stands in front of the Treasury building in Washington, and observes that the wrong in the story is not the insider trading but the bailout, as Zadek described it. Legalize Insider Trading (2009)
The Reynolds affair
The 2013 episode on California government opens with Bob Zadek discussing the political returns of Elliot Spitzer and Anthony Weiner, then turns to what he calls probably the first sexual scandal in the country. Zadek states that in 1791, when the country was three years old, Alexander Hamilton—whom he calls perhaps the second most powerful politician in the very young country and George Washington’s Secretary of the Treasury—had an affair with Maria Reynolds. According to Zadek, she seduced him, she was married and he knew it, and she claimed her husband was abusing her and that she needed help. Zadek says it is probably the case that her husband knew all along, that he began blackmailing Hamilton, and that Hamilton paid the blackmail. The affair and the blackmail payment came out, and in 1796 Hamilton published a very long public apology, including all the love letters he wrote with Maria Reynolds, explaining that while his behavior was terrible and he was ashamed, he did not otherwise violate the public trust. Zadek notes an accusation that Hamilton used public money to pay the blackmail, which he says was never really seriously pursued. As a postscript, Zadek recalls that Aaron Burr killed Hamilton in a duel on the cliffs of Weehawken, New Jersey, in 1803, and adds that Burr was Maria Reynolds’ divorce lawyer. California Dreamin’ – About Sane Government (2013)
The “least dangerous branch”
In the 2019 episode on the Supreme Court, Bob Zadek introduces David Kaplan, author of The Most Dangerous Branch, and notes that the book’s title is a play on words. Zadek says that during the Revolutionary era, in the Federalist Papers, Hamilton wrote in Federalist 78—adding that he could be wrong about the number—that the Supreme Court was the “least dangerous branch” because it had neither arms nor a purse, and could only say what it thought without power to enforce what it believed to be the law of the land. Zadek tells Kaplan that Hamilton, who knew a whole lot about a whole lot of things, maybe got his view of the Supreme Court wrong, and that the Court has become far more powerful than the founders envisioned. Kaplan’s discussion of the Court’s power, the death of Scalia, Justice Kennedy’s role, and the turn to judicial solutions for problems Congress will not solve follows from that framing. Demystifying the Supreme Court (2019)
Sovereignty at the Framers’ Convention
In the 2020 episode on California and nation-statehood, Frank Buckley tells Bob Zadek that the idea of independence brings with it the concept of sovereignty, and that when the country was founded, sovereignty was a stumbling block for the British, who could not conceive that America or the individual colonies could be sovereign in any respect—there could be only one sovereign. Buckley says some people at the Framers’ Convention echoed that view, and that Alexander Hamilton did. But, Buckley says, that was not the document that came out of Philadelphia in 1787; instead there was an idea of divided sovereignty, with the state sovereign as to state powers and the federal government sovereign as to its powers. Buckley describes this as the original conception of America, and says the line has since been blurred and state sovereignty fell into ill repute because of the way it was used by racists in Southern states. Did California Just Declare Itself a Nation-State? (2020)
The Whiskey Tax
In the 2022 episode on the Inflation Reduction Act, Thomas DiLorenzo tells Bob Zadek that the most atrocious element of the act is the plan to hire 87,000 new IRS agents, reportedly 70,000 of them armed, and says Americans once fought a revolution over such a thing. He cites the Declaration of Independence’s complaint that King George III sent swarms of officers into homes to eat out the substance of the people—armed tax collectors who barged into homes with guns to enforce the Stamp Tax and other taxes—and says the revolution got rid of that. DiLorenzo then says that after the revolution it was Alexander Hamilton who wanted to bring it back: a Whiskey Tax was imposed, Western Pennsylvania farmers protested and refused to pay, and they tarred and feathered federal tax collectors who came around. According to DiLorenzo, Hamilton talked George Washington into taking some 13,000 soldiers into Western Pennsylvania to enforce the Whiskey Tax; it turned into a bust, Washington went home, two protesters were convicted of tax evasion, and Washington pardoned them both. DiLorenzo calls this the first attempt to resurrect an army of armed tax collectors. Lies, Damned Lies & the Inflation Reduction Act (2022)
Across episodes
Hamilton is invoked in five episodes spanning 2009 to 2022, but the excerpts show no development in the treatment of him: each episode uses him for a different argument—insider trading and bailouts, private conduct and public office, judicial power, divided sovereignty, and armed tax enforcement—and no guest or host revisits or revises an earlier characterization. The 2009 and 2013 episodes both place him in the 1790s and both concern his personal conduct in office, but they address different episodes and draw different lessons.
What the sources do not cover
The excerpts contain no account of Hamilton’s early life, his role in drafting the Federalist Papers beyond the single attributed essay, his tenure at the Treasury beyond the debt-assumption story, or his death beyond the duel’s location and year. They do not state his birth or death dates, his title at any point other than Secretary of the Treasury, or the content of any policy he advanced apart from the assumption of state debt and the Whiskey Tax. Where the excerpts break off mid-sentence—as in the 2009 and 2020 episodes—nothing further about Hamilton is stated.