The definition of blackmail—the act of demanding that a person pay money or do something in order to avoid having damaging information about him or her exposed—has evolved over time. The word’s origins are linked to the chieftains in the border region between England and Scotland in the 16th century and part of the 17th century. During that period, the chieftains ordered landholders to pay them in order to avoid being pillaged. The “mail” in the word meant “tribute, rent” and was derived from an old Scandinavian word, “mal,” meaning “agreement.” The “black” in blackmail is thought to be a play on “white money,” the term for the silver coins with which tenant farmers traditionally paid their legitimate rent.

One of America’s earliest political sex scandals involved blackmail. In 1791, Alexander Hamilton, then America’s first treasury secretary as well as a married man, became romantically involved with Maria Reynolds, a young woman who claimed she needed money because her husband had abandoned her. When Reynold’s husband, James, reappeared on the scene, he forced Hamilton to pay him in order to keep quiet about the affair. After James Reynolds later got caught in a plot to defraud the federal government, he attempted to implicate Hamilton in the scheme. Confronted by James Monroe and several of his congressional colleagues, Hamilton denied any involvement in the scheme but admitted to his liaison with Maria Reynolds. He gave the congressmen letters from both of the Reynolds that indicated his involvement with James had been about the affair not a financial scheme. Convinced that Hamilton wasn’t involved in government corruption, the congressmen agreed to drop the matter. However, partisan political writer James Callender subsequently got his hands on the letters and in 1797 published the story of Hamilton’s secret affair, while also charging that his payments to James Reynolds were part of a plot to swindle the government. Hamilton, in turn, published a detailed response in which he admitted to marital infidelity but denied the financial corruption charges. The former treasury secretary, who’d left his post in 1795 to return to practicing law, survived the scandal (and even made it onto the face of the $10 bill) but died in 1804 after being mortally wounded by Aaron Burr in America’s most famous duel.