Federalists Versus Anti-Federalists on Six Questions, Side by Side

They say history is written by the winners. The ratification fight of 1787 and 1788 is the glorious exception. The winners wrote eighty-five newspaper essays, and the losers' demands became the first ten amendments to the Constitution. If you have ever invoked your right to a jury, quoted the Second Amendment, or reminded a federal bureaucrat that powers not delegated are reserved to the states, you were quoting the side that lost.

That is a strange result for a political fight, and it is worth understanding precisely. The debate was not a shouting match between friends and enemies of liberty. It was a disciplined argument over six concrete questions, and the two sides gave different, carefully reasoned answers to each. Lay them side by side and you can see exactly where each camp was right, where each was wrong, and how the Anti-Federalists turned defeat into a permanent seat at the constitutional table.

The two camps, defined

First, the labels, because they are slippery.

Federalists supported ratification of the Constitution as written, with amendments, if any, to follow. Their best-known writers were Alexander Hamilton, James Madison and John Jay, writing together as Publius in The Federalist, along with James Wilson of Pennsylvania, whose public speeches in 1787 framed many Federalist arguments.

Anti-Federalists opposed ratification without prior amendments, or opposed it altogether. They were never a single party. Their ranks included George Mason and Patrick Henry of Virginia, the pseudonymous essayists Brutus and the Federal Farmer in New York, Centinel in Philadelphia, and many delegates in the state conventions. Some wanted the Constitution rejected outright; most wanted it amended first.

A wry note on the names. The opponents of the Constitution were, if anything, the truer federalists, because they wanted to preserve a federation of sovereign states. The supporters took the attractive label first, and their opponents were stuck being "anti" something that sounded pleasant. Political branding, it turns out, was invented before the steam engine.

The six questions at a glance

Now each question in turn, with a verdict.

Question 1: the size of the republic

The Anti-Federalists had the weight of political science behind them. Montesquieu taught that republics belonged to small territories. Brutus applied that teaching to a nation stretching from New Hampshire to Georgia and concluded that only force could hold it together.

Madison's answer was one of the great original arguments in political thought. Representation, he wrote in Federalist 14, means only the representatives need to assemble, so a republic can extend over a large region. And size is a benefit: in Federalist 10, "Extend the sphere, and you take in a greater variety of parties and interests; you make it less probable that a majority of the whole will have a common motive to invade the rights of other citizens."

Verdict: Federalists. Two centuries of continental self-government settled this one. (See Madison Explained the Republic Versus Democracy Difference in Federalist 14 and Brutus No. 1 Predicted the Necessary and Proper Clause Would Swallow the States.)

Question 2: representation

The Federal Farmer argued that sixty-five representatives could not reflect the variety of American life, and that large districts would favor a "natural aristocracy" of wealth and fame. Madison replied in Federalist 55 that "Had every Athenian citizen been a Socrates, every Athenian assembly would still have been a mob," and promised the House would grow.

It did grow, until Congress capped it at 435 after the 1910 census and the Permanent Apportionment Act of 1929 locked that number in place. The First Congress proposed an amendment to guarantee growth; it was never ratified.

Verdict: split. Madison was right about mobs; the Farmer was right that growth should not depend on the convenience of incumbents. (The full story is in The Federal Farmer Wanted a Bill of Rights and a Bigger House.)

Question 3: the taxing power

Under the Articles of Confederation, Congress could only request money from the states, and the states routinely ignored the requests. Hamilton's answer in Federalist 30 to 36 was blunt: money is the vital principle of the body politic, and a government that cannot raise it cannot function. Brutus answered that a general taxing power, backed by the Supremacy Clause, would let the national government take what it liked and leave the states the scraps.

Several ratifying conventions, Massachusetts among them, recommended an amendment limiting direct federal taxes to cases where import duties fell short. It was not adopted. The Constitution did keep a structural limit: direct taxes had to be apportioned among the states by population. When the Supreme Court in Pollock v. Farmers' Loan & Trust Co. (1895) held that an unapportioned income tax on income from property was unconstitutional, the country answered with the Sixteenth Amendment in 1913, allowing income taxes without apportionment. (That amendment's sales pitch is examined in The 16th Amendment Began With a Promise That Only the Rich Would Pay.)

Verdict: Federalists on the principle, Anti-Federalists on the consequences. A national government needed its own revenue. But once the apportionment limit fell, the taxing power, combined with grant conditions, became the main tool for bending the states, exactly as Brutus warned. Look at the national debt clock if you doubt the scale.

Question 4: the courts

Hamilton's Federalist 78 called the judiciary the least dangerous branch because it has "neither FORCE nor WILL, but merely judgment." Brutus answered that life-tenured judges, deciding cases by the spirit of the Constitution rather than its letter, would enlarge federal power one case at a time, with no one able to correct them.

The first test came quickly. In Chisholm v. Georgia (1793) the Supreme Court allowed a citizen of another state to sue Georgia in federal court. The states were alarmed, and the Eleventh Amendment, ratified in 1795, reversed the decision. In the twentieth century, federal courts removed question after question from the states, some rightly under the Fourteenth Amendment and some, like abortion until Dobbs (2022), wrongly.

Verdict: Anti-Federalists, mostly. Hamilton's description of judicial modesty is the ideal; Brutus's description of judicial expansion is the history. The cure is judges who believe Hamilton.

Question 5: the standing army

Here the Federalists conceded more than people remember. Article I, Section 8 gives Congress the power "To raise and support Armies, but no Appropriation of Money to that Use shall be for a longer Term than two Years." That two-year limit was itself an answer to the fear of a permanent army beyond the people's control. Madison argued in Federalist 46 that any federal army would be dwarfed by the armed citizenry of the states organized in militias.

The Anti-Federalists still wanted more, and they got two amendments out of it. The Second Amendment secured the people's right to keep and bear arms, tied to a well regulated militia, and the Third barred quartering soldiers in private homes in peacetime without the owner's consent. District of Columbia v. Heller (2008) confirmed that the Second protects an individual right, and McDonald v. City of Chicago (2010) applied it to the states.

Verdict: split. The army power stayed broad; the armed citizen was written into the text.

Question 6: a bill of rights

The hinge of the whole debate. Hamilton argued in Federalist 84 that a bill of rights was unnecessary and even dangerous, since it would list exceptions to powers never granted. Mason, Henry and the Federal Farmer argued that rights left unwritten are rights left to lawyers.

The Anti-Federalists won this one decisively, and they won it in the ratifying conventions. Massachusetts ratified on February 6, 1788, by 187 to 168, while recommending amendments, a formula that let wavering delegates vote yes. New Hampshire became the ninth state on June 21, 1788. Virginia followed on June 25 by 89 to 79, and New York on July 26 by 30 to 27, both with long lists of recommended amendments. Madison, who had doubted a bill of rights, promised to deliver one, and on June 8, 1789, he introduced amendments in the House.

Verdict: Anti-Federalists. (Hamilton's case and its answer are in Hamilton Argued in Federalist 84 That a Bill of Rights Could Be Dangerous; the Virginia showdown in Patrick Henry Against James Madison, the Richmond Debate That Decided Virginia; the Massachusetts formula in Massachusetts Saved the Constitution in 1788 by Ratifying and Asking for More.)

How the losers won the argument

Add up the verdicts. The Federalists won the vote, the structure and two of the six questions outright. The Anti-Federalists won the bill of rights outright, won the courts question on the historical record, and split the other two. That is a remarkable showing for a side that lost the decisive ratifying conventions in Massachusetts, Virginia and New York.

Their victory took three forms.

1. The Bill of Rights. Ratified in 1791, it turned the Anti-Federalists' demands into the most quoted text in American law. The First Amendment's "Congress shall make no law" is written as a limit on a branch, which was precisely the Anti-Federalists' point: power must be fenced in writing.
2. The Tenth Amendment. "The powers not delegated to the United States by the Constitution, nor prohibited by it to the States, are reserved to the States respectively, or to the people." This turned the Federalists' own promise of enumerated powers into a binding rule of construction. Notably, Congress refused to insert the word "expressly" before "delegated," which the Anti-Federalists wanted, and that omission has shaped every federalism case since. (See The Tenth Amendment Left Out One Word, Expressly, and the Omission Mattered.)
3. A permanent tradition of suspicion. Every later argument for limited government, from the Virginia and Kentucky Resolutions of 1798 to modern federalism cases like United States v. Lopez (1995), draws on Anti-Federalist reasoning. They became the Constitution's loyal opposition.

The best objection, and the answer

The objection. Romanticizing the Anti-Federalists is a mistake. Many of them wanted to keep the Articles of Confederation, which had failed. Some opposed the Constitution partly because it threatened local power structures, including, in some states, interests tied to slavery. If they had won, there would have been no strong union to fight the Civil War, end slavery and pass the Fourteenth Amendment.

The answer.

1. Fair on the Articles: most Anti-Federalists conceded the Articles needed repair, and the ones who did not were wrong. That is why the vote went the way it did, and rightly.
2. Motives were mixed on both sides. Slaveholders were prominent among Federalists too; Madison and Washington both held slaves. The debate should be judged by its arguments, not by a selective accounting of motives.
3. The point is not that the Anti-Federalists should have won. It is that the Constitution became better because they lost the vote and kept arguing. The Federalists built the house. The Anti-Federalists installed the locks.

The case in brief

1. The ratification debate turned on six questions: the size of the republic, representation, taxation, the courts, the standing army and a bill of rights.
2. The Federalists won the first question outright and the principle of a national taxing power.
3. The Anti-Federalists won the bill of rights outright and were vindicated on the growth of judicial power.
4. Representation and the army ended in a split, with the Second and Third Amendments as the Anti-Federalist share.
5. The Bill of Rights and the Tenth Amendment are the losers' permanent victory, and they still limit the winners' government.

What you can do: put this table in front of a teenager you know, ask them to pick a side on each question, and then have them read the Tenth Amendment on the Constitution page.