Can You Match the Founding Father to the Scandal?



By: Jenna Dennison

6 Min Quiz

Image: Federica Grassi / Moment / Getty Images

About This Quiz

You know their names, but what do you really know about the secrets of America's Founding Fathers? When we think of such influential men as George Washington, Thomas Jefferson and Alexander Hamilton, along with other members of such an esteemed group, we rarely reflect on the schemes they've been connected to. Who would've guessed that so many of these significant figures were entangled in illicit affairs, violent duels and a collection of other strange events? In fact, did you know one of the most famous Founding Fathers kept skeletons in his home's basement?

Undoubtedly, America would not be the same without the ingenuity, bravery and intelligence of these men. Without the Founding Fathers, we would not have the Declaration of Independence, the United States Constitution or the form of government we experience today. We must not forget the massive contributions this group made to the welfare of the nation, as well as where their work has brought us to today. 

You might have thought that you knew everything about the nation's Founding Fathers, but can you match these Founding Fathers to their shocking scandals? It turns out your history classes left out some of the most interesting details about these men!

Which Founding Father had over fifteen skeletons in the basement of his home?

Before signing the Declaration of Independence, Benjamin Franklin rented a home on 36 Craven Street in London. Over 200 years later, human bones dating back to Franklin's time were found in the basement. Experts believe that one of Franklin's acquaintances, William Hewson, was running an illegal anatomy school out of the basement.


Undoubtedly, the events of Alexander Hamilton's life were quite fascinating. What was Hamilton accused of by James Monroe?

Monroe suspected Hamilton of embezzling government funds when he discovered Hamilton had sent large sums of money to a man named James Reynolds. However, when Monroe confronted Hamilton, he learned that these were blackmail payments that Hamilton had personally made.


While the American presidency was in its early stages, some individuals had unique ideas about how the president should be addressed. What Founding Father demanded that Washington be referred to as "His Highness"?

In a move that proved to be unpopular, John Adams requested that the president be referred to as "His Highness, the President of the United States of America, and Protector of the Rights of the Same" in order to reflect the importance of the office. However, his request was ridiculed by the Senate and the press.


Duels were, at one time, a way to deal with a conflict between two parties. Which Founding Father engaged in a duel with Aaron Burr?

Aaron Burr and Alexander Hamilton dueled in Weehawken, New Jersey, on July 11, 1804. Burr, who was serving as the third vice president at the time, fatally wounded Hamilton in the duel.


Who broke the news to the public that Jefferson was having a relationship with one of his slaves?

In 1802, James Callender published the first known report about Thomas Jefferson's involvement with Sally Hemings. In Callender's writings, he calls Hemings the "concubine" of Jefferson.


Alexander Hamilton was once suspected of mismanaging government money. What is the name of the document Hamilton published in 1797 regarding these rumors?

The document Hamilton wrote was titled "The Reynolds Pamphlet," in which he denied that he had embezzled government money. Instead, he confessed to having an affair with a woman named Maria Reynolds.


British-imposed taxes greatly affected the American colonies. What Founding Father was known for smuggling goods into the colonies to avoid taxation?

John Hancock's ship, Liberty, was seized by British forces when it was discovered he was smuggling goods into the colonies to avoid taxes imposed by the Stamp Act. In fact, Hancock received help from John Adams to avoid facing smuggling charges.


The Founding Fathers were sometimes involved in dangerous situations. What Founding Father had a bounty placed on his head?

Due to Hancock's smuggling practices, the British placed a bounty on his head. Hancock, however, was offended at how little his bounty was worth and suggested they should double it.


British forces desperately wanted to punish those who avoided paying taxes. How much was the bounty placed on Hancock's head?

John Hancock smuggled goods into the colonies in order to avoid paying British taxes. However, British forces became aware of this activity, and they placed a £500 bounty on his head.


The Sons of Liberty were the driving force behind the Boston Tea Party. However, which Founding Father played a significant role in coordinating this event?

After the Royal Governor refused to let British tea leave Boston Harbor, Adams famously proclaimed, "This meeting can do nothing more to save the country!" Some historians believe that this statement served as a signal to the Sons of Liberty to destroy the tea in the harbor. In fact, Adams congratulated the Sons of Liberty after the Boston Tea Party.


In a decision that would have been treated as espionage at the time, which Founding Father illegally smuggled rice into the United States?

After seeing that Italian Piedmont rice sold better than American rice in Paris, Jefferson decided to illegally bring the new variety of Italian rice to the United States. In fact, Jefferson believed that "the greatest service which can be rendered any country is to add an useful plant to it's [sic] culture."


Dueling was not an unusual way to settle arguments during this time in American history. Which Founding Fathers almost dueled each other?

Alexander Hamilton and James Monroe almost dueled each other in 1797. Hamilton believed that Monroe had leaked private documents about his affair with Maria Reynolds to the press, and he was prepared to duel Monroe to maintain his dignity.


Sally Hemings had six children with Thomas Jefferson. What made Hemings' children different from most other children born into slavery?

While only four of the six children Sally Hemings had by Jefferson lived into adulthood, Jefferson freed all four of her living children. No other families at Monticello were ever freed by Jefferson.


How much money did James Reynolds extort from Alexander Hamilton in order to cover up Hamilton's affair?

Alexander Hamilton paid James Reynolds $1,000 to keep his affair with Reynold's wife, Maria, a secret. Afterward, Reynolds even encouraged Hamilton to maintain his relationship with Maria.


What Founding Father was involved in the XYZ Affair?

John Adams faced trouble in his presidency when France began to prevent American ships from trading with the British. The French minister demanded bribes from the American government before negotiations could begin, but the Adams administration never paid. Once word got out to the public, this situation became known as the XYZ Affair — with X, Y and Z standing for the French officials involved.


What events occurred following the XYZ affair?

By July 1798, the U.S. had retracted all of its treaties with France, and American ships began to attack the French Navy. These events launch the Quasi-War, which was only settled when the Treaty of Mortefontaine was ratified in 1801.


In what year did Sally Hemings have her first child, fathered by Thomas Jefferson?

Sally Hemings had her first child in 1790, when she was sixteen years old. However, this child was never named and died in infancy. Hemings' son, Madison, would later write that this first child "lived but a short time."


Which Founding Father had an illegitimate child who later governed New Jersey?

Benjamin Franklin had an illegitimate son, William Franklin, around the time of 1730. However, William would later be exiled in jail due to his loyalty to the British, as he served as the Royal Governor of New Jersey.


What signer of the Constitution was later removed from the U.S. Senate?

William Blount, one of the signers of the Constitution, lost his seat less than a year after he was elected as a senator for the state of Tennessee. On August 2, 1796, Blount's fellow senators found him guilty of "a high misdemeanor, entirely inconsistent with his public trust and duty as a Senator."


For what reason did William Blount lose his seat in the Senate?

William Blount attempted to help the British capture Spanish land in West Florida by creating tension between the Cherokee and Creek tribes. However, Blount's plans were exposed, and he was expelled from his position in the Senate in 1797.


What Founding Father was fond of "air baths"?

In Franklin's opinion, he was able to produce his best work when he had a morning "air bath." Essentially, Franklin would sit by an open window in the nude for around 30 minutes to an hour.


What Founding Father sent love letters to another woman while he was engaged?

While engaged to Martha Custis, George Washington maintained a romantic correspondence with Sally Fairfax, a wealthy Virginia woman he had known since his teenage years. In one letter to Fairfax, Washington wrote, "The world has no business to know the object of my love, declared in this manner to you, when I want to conceal it."


Which Founding Father allegedly had an affair with Dolley Madison?

Dolley Madison often assisted Thomas Jefferson as a social hostess when he held presidential events, since his wife had died years before. However, some speculated that Dolley was his mistress — they thought Dolley had a relationship with Jefferson in order to secure favorable votes for her husband, James Madison, in the upcoming presidential election.


What Founding Father destroyed some of his early writings?

Not long after creating it, Benjamin Franklin sought out and destroyed copies of his 1725 pamphlet, "A Dissertation on Liberty and Necessity, Pleasure and Pain." He came to regret this piece of work he had created at the age of nineteen.


Under what circumstances did Hamilton and Burr decide to duel?

Hamilton trusted Burr very little; he viewed Burr as an opportunistic politician. In fact, Hamilton garnered support within his political party to ensure Burr would not win the presidency in 1800. Burr was furious with Hamilton's comments and demanded an apology, which Hamilton refused to give. Due to Hamilton's refusal, the two decided to duel.


What idea did Franklin's "A Dissertation Upon Liberty and Necessity, Pleasure and Pain" promote?

"A Dissertation Upon Liberty and Necessity, Pleasure and Pain" reflected Franklin's beliefs that humans lack free will. Franklin soon regretted writing this pamphlet and destroyed all copies that he could find. A few survived, however.


Who was suspected of leaking documents about Hamilton's affair to the press?

Privately, Hamilton revealed documents regarding his affair to a few individuals, which included James Monroe. Hamilton himself suspected that Monroe leaked the documents to James Callender, a gossip writer at the time. Hamilton's wife, Eliza, allegedly held a grudge against Monroe for his supposed actions.


What Founding Father snubbed President George Washington?

During a ten-day trip to Massachusetts, President George Washington was greeted by crowds and high ranking officials. One notable absentee was John Hancock. In Hancock's mind, he was more notable than Washington, as Hancock was the governor of the Commonwealth of Massachusetts.


How did Sally Hemings leave Monticello?

Thomas Jefferson died in 1826. While all of Sally Hemings' children by Jefferson had been freed, Hemings was "given her time" by Jefferson's daughter, Martha, after his death. Hemings then went to live with her sons, Madison and Eston Hemings, in Charlottesville, Virginia.


Who stopped Hamilton and Monroe from dueling?

Monroe called on his friend Aaron Burr to help him negotiate the duel with Hamilton. It was Burr who eventually convinced Hamilton and Monroe that a duel between the two would be quite "childish."


Which Founding Father was known for his fiery temper?

While he was able to subdue himself as he grew older, George Washington was known for having an explosive temper. Regarding Washington's temper, Thomas Jefferson wrote, "His temper was naturally irritable and high-toned, but reflection and resolution had obtained a firm and habitual ascendency over it. If, however, it broke its bonds, he was most tremendous in his wrath."


What Founding Father was charged with committing treason?

In 1807, Aaron Burr was charged with treason by President Thomas Jefferson. Jefferson discovered that Burr had been plotting to establish an independent republic in the Southwest. However, Burr was found not guilty of treason at the end of his trial.


During this time in American history, it was not uncommon (or illegal) for slavemasters to have relationships with female slaves. What Founding Father had six children by one of the slaves he owned?

Thomas Jefferson had six children by one of the slaves he owned. However, only four of these children survived into adulthood. Jefferson's three sons, Beverly, Madison and Eston, became carpenters. His daughter, Harriet, worked as a spinner in one of the factories at Monticello.


Which Founding Father was held responsible for his stepson's debts?

In 1794 James Madison married Dolley Payne Todd, who had a young son from a previous marriage. Madison's stepson had gambling problems and spent time in a debtor's prison. Madison ended up paying around $40,000 to clear his stepson's debts, largely without sharing this information with his wife.


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