Tuesday, June 17, 2025

AI Counterfactual History: Shay's Rebellion and Constitutional Convention

Here's some interesting counterfactual history from Chat GPT, based on my current book, THE GREAT UPHEAVAL (1780-1800) by Jay Winik.

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The Declaration of Independence was 1776, and then they soon wrote the Articles of Confederation, which wasn't adopted til 1781, which was still 2 years before the end of the war (1783).

The Articles of Confederation led to all sorts of conflicts among the states, including inter-state taxes and tariffs, bringing us the new Constitutional Convention in 1788.

Along the way, there was a notable and armed taxpayor revolt against the courts and legislatures in Massachusetts and other states (Shay's Rebellion), which petered out.   

Winik notes the rebels had no political success, otherwise they would have gotten into state legislatures.  Had they done that, they would have selected like-minded delegates to the Constitutional Convention, which could have changed everything.

Here's a counterfactual where that happens.

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Write a counterfactual history where Shays Rebellion supporters win a range of different state elections, and therefore choose many of the State delegates to the new constitutional convention of 1788-1789.

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Absolutely — here’s a vivid counterfactual scenario exploring what might have happened had Shays' Rebellion sparked a broader political movement, powerful enough to reshape the constitutional process itself.

🧨 Counterfactual History: The Shays Convention of 1788–1789

🔁 Point of Divergence: Fall 1787

After the suppression of Shays’ Rebellion, instead of retreating, its supporters organize into a populist agrarian movement across New England and the Mid-Atlantic. They form a loose coalition called the Continental Reform League (CRL), dedicated to:

  • Eliminating hard money debt enforcement

  • Opposing centralized economic control

  • Defending states’ rights

  • Demanding protections for farmers, debtors, and laborers

Local victories in Massachusetts, New Hampshire, Rhode Island, and parts of Pennsylvania and New York give the CRL enough strength to win state legislative majorities, and with it, the ability to appoint delegates to a second constitutional convention in 1788.

🏛️ The 1788–89 Convention: A Different Room in Philadelphia

The new convention, originally intended to resolve final gaps in ratification and discuss amendments (especially the emerging Bill of Rights), is instead flooded with CRL delegates. George Washington, weary of factionalism, declines to attend.

Key delegates now include:

  • Elbridge Gerry (MA) — now leading a powerful anti-centralization bloc

  • Melancton Smith (NY) — a fiery voice for anti-elite politics

  • Thomas Paine, invited as an observer and agitator, gives speeches in taverns nightly

Alexander Hamilton and James Madison arrive, alarmed. Their Federalist allies are outnumbered.

📜 A Very Different Constitution Emerges

The resulting document — the Compact of Free States — keeps some elements of the original 1787 Constitution but radically alters others:

🧷 Key Features:

  • No Supreme Court; instead, a decentralized “council of state courts”

  • Congress cannot charter a national bank or assume state debts

  • Each state can issue currency (subject to loose federal oversight)

  • Presidency is ceremonial — a Council of Delegates chooses a “Chief Officer of Union Affairs” for a 1-year term

  • Treaties require a ¾ vote of state legislatures, not just the Senate

  • A binding Debtors’ Bill of Rights is included — forbidding imprisonment for debt and protecting homesteads from seizure

🔁 Consequences Over the Next 20 Years (1790–1810)

💰 Economic Turbulence

  • Competing state currencies and retaliatory tariffs return

  • Southern states refuse to cooperate with Northern economic policies

  • Western farmers regularly defy eastern merchant debt collectors — now with legal protections

⚔️ Foreign Policy Paralysis

  • The federal “Union” is too weak to respond to British provocations or trade abuses

  • The War of 1812 never happens — instead, Virginia negotiates its own trade pact with Britain, infuriating New England

🌉 Secession Movements Emerge Early

  • By 1805, New Englanders form a Continental Congress of Commercial States, threatening to leave the Union unless reforms are made

  • Meanwhile, a Western Farmers’ Convention in Ohio advocates full land debt cancellation and abolition of banks

🧠 Historical Reflection

In this alternate timeline, Shays' legacy becomes enshrined, but at a cost:

  • The U.S. becomes a confederation of bickering mini-republics

  • The dream of a unified American commercial empire collapses

  • A stronger federal government eventually emerges… but not until a civil conflict in the 1830s, led by a new generation of "Unionists."

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