Reprint from Mental Floss.

From a German immigrant who arrived in America with nothing to a cousin of Queen Elizabeth II, the Astor family’s story is one of hard work, ruthless business tactics, snobbery, and savvy investment in real estate. For more than a century, they were the richest family in America, and their shrewd marriages linked them to some of the most politically powerful families. Here are 11 facts about this fascinating family.

1. The Astor fortune was partly founded on drug smuggling.

John Jacob Astor I. / Oscar White/GettyImages

The wealth of the Astor family originated in fur trading, guided by the intelligent but ruthless business tactics of their American founder, John Jacob Astor I. Having tried his hand at being a butcher like his father and an instrument maker like his brother, John I emigrated to America in 1783. He used the voyage to learn about the fur trade.

Always on the look out for a new opportunity, he began trading with China in around 1800, but the Chinese were resistant to Western goods—so in 1816, Astor became involved in the lucrative opium smuggling trade.

Opium was first banned in China in 1729 in an attempt to halt a growing epidemic of users, but 115 metric tons were still being imported into the country in 1798. With the Indian supply of the drug monopolized by the British, Astor made deals to buy huge quantities from Turkish suppliers, which he smuggled in via small vessels and large bribes. During his involvement between 1816 and 1825, the amount of opium being smuggled into China continued to rise­; by 1839, 2500 metric tons entered the country from India alone.

Astor made millions from a trade the future U.S. President Franklin D. Roosevelt described as “fair, honorable, and legitimate.” He used the money to buy tea, porcelain, and silks, which he imported into America at a huge profit. Astor used that fortune to invest in New York real estate, and by the time of his death in 1848, he was America’s first ever millionaire.

2. John Jacob Astor I’s wife was so good at the business, she reportedly charged her husband $500 an hour.

John married Sarah Cox Todd in 1785. She was the daughter of his landlady—and had a $300 dowry, plus connections to sea captains, merchants, shop owners, and ship owners. Her dowry allowed them to open their first shop selling musical instruments, which gradually gave them the opportunity to invest in furs.

Astor called his wife “the best business partner any man ever had.” He would always credit Sarah’s part in his success, not just in the connections that she brought or the financial independence that her dowry allowed him, but also in her business acumen. Sarah’s knowledge of furs grew until she had turned herself into a leading expert in quality pelts; when John was away, she ran their New York business.

She was shrewd, thrifty, and intelligent, involved in both day-to-day decisions and plans for how they would expand their enterprises. Sarah encouraged John to invest in real estate, the foundation of their multi-million dollar fortune.

By the end of her life they were so successful that John reputedly paid her $500 an hour for her work, which she invested in religious causes.

3. Caroline Schermerhorn Astor ran America’s social hierarchy, known as the “four hundred.”

Caroline Schermerhorn Astor. / Print Collector/GettyImages

In the New York of the 1880s and 1890s, if you wanted to be accepted into society, it was not enough just to be wealthy. Anyone could have money in the fast moving and socially mobile America of the Gilded Age—what was important was to have the right sort of money.

Although America did not have a class system in the same way as much of Europe, the families who were descended from New York’s original settlers and had inherited their money considered themselves the aristocracy of American society. Those making their fortunes from new industries like the railroad were upstarts who, although sometimes even richer than the old money crowd, would never quite fit in.

At the forefront of these old families were the Astors. Now 100 years on from the self-made John Jacob Astor I, they believed that as old money, they had a superior role in New York society. Caroline Schermerhorn was descended from the Dutch immigrants who had settled Manhattan in the 17th century—and she had even considered the Astors beneath her own pedigree when she married John I’s grandson, William Backhouse Astor II, in 1853.

Caroline put herself at the forefront of fashionable society, establishing a hierarchy of people who met her standards of etiquette, behavior, and breeding that became known as The Four Hundred. Legend has it that the number was arrived at simply because it was the capacity of the Astor’s ballroom, but, whatever the reason, membership was essential for anyone who wanted to be someone in New York. Budding social climbers would engineer ways to get Mrs. Astor’s approval. But, as the Vanderbilts and others discovered, her approval was not easy to get—and her word was always final.

4. The family was torn apart by a feud about who would be called Mrs Astor.

John Jacob Astor I’s second son, William Backhouse Astor Sr., inherited his fortune; he in turn passed it to his two sons, John III and William Backhouse Jr. But if he thought the two sides of the family would live in harmony, his plan was thwarted by a disagreement over who would be known as Mrs. Astor.

John III and William Jr.’s wives were known by their husband’s names—Mrs. John Charlotte Astor and Mrs. William Caroline “Lina” Astor. When Charlotte died in 1877, Lina let it be known that she was now to be addressed as simply Mrs. Astor.

The Astors believed in elder sons taking precedence, and Charlotte’s son, William Waldorf Astor, took enormous exception to the fact that this seemingly innocuous act threatened the superiority of his line. It was also an insult to his own wife, Mary, who he considered the senior woman of the family.

John III died three years later, and William Waldorf became the head of the family. Using his new position, he tried to persuade his Aunt Lina to relinquish the use of the title, but with her position in society to maintain, she refused. She continued to be known as the Mrs. Astor.

Although William Waldorf was forced to concede, he had his revenge and the incident created a feud between the two branches of the family that would last years: The brothers, John III and William II, had lived in neighboring houses on 5th Avenue, but after John’s death, his son demolished their house in 1893 and built the 13-story Waldorf Hotel on the site, right next to Aunt Lina.

She spent the next three years living next to a building site. The humiliation of her prestigious residential area becoming a bustling tourist destination was more than she could bear, and she was finally persuaded to move. But her humiliation wasn’t quite over—her new home was farther up 5th Avenue, surrounded by the new money families.

In true Astor fashion, her son, John Jacob Astor IV, used the episode to make more money. Following his cousin’s example, he demolished the family house and built a 16-story hotel called the Astoria in 1897. That same year, the family merged the two hotels in a new business venture: The Waldorf-Astoria Hotel. The original structure was demolished in 1929 and replaced by the Empire State Building.

5. William Waldorf Astor moved the senior branch of the family to Britain.

William Waldorf Astor. / Hulton Archive/GettyImages

The difficulties with his aunt would have an unexpected outcome for William Waldorf Astor. Not only did it lead him into the hotel business, but it also resulted in his emigration to Britain.

Although he was born in New York, William Waldorf was raised in Italy and Germany, where he developed a passion for the European lifestyle. He returned to America and studied law, but after a short period involved in politics—where he unsuccessfully ran for Congress—he returned to Europe in 1882 for three years as the U.S. Minister to Italy.

On his father’s death in February 1890, he reportedly inherited $100 million, and, disillusioned with his failure in politics, upset by the war with his aunt and her son, and ridiculed by the U.S. press, William Waldorf declared that America was “no longer a fit place for a gentleman to live” and moved his family and business operations to Britain.

He retained his interest in politics, giving generously to the Conservative Party. Despite his hatred of the American press, he bought several UK publications, including The Observer newspaper. In 1899 he became a British citizen, and in 1917 he was raised to the British peerage when George V created him the 1st Viscount Astor of Hever.

6. The Astors once owned Hever Castle, the childhood home of Anne Boleyn.

Hever Castle in Kent was built in 1270, but its most famous residents were the Boleyn family, who had owned it between 1462 and 1540. It was Anne Boleyn’s childhood home and, after returning from France in 1522, she frequently stayed at the castle with her parents, enticing Henry VIII to visit on several occasions during their courtship. Later, Henry’s fourth—and unwanted— wife, Anne of Cleves, lived there, leasing the manor for an annual rent of £9, 13 shillings, and 3.5 pence.

By the time William Waldorf purchased Hever in July 1903, the house had passed through several families and was almost derelict, with all traces of its Tudor gardens gone. But, as a history buff—who had written several historical novels—with a passion for art and architecture derived from his time spent in Italy, he immediately recognized its potential.

The series of renovations William undertook were sensitively done, preserving the original structure while installing modern luxury. Part of his vision included building a new wing in the style of a Tudor village, and he redesigned the 125-acre gardens to incorporate a 38-acre lake, an Italian loggia, a rose garden, a Tudor garden, and a woodland. Under Astor ownership, Hever Castle was saved. People can still visit the historic site today.

7. Nancy Astor was the first woman to take a seat as a Member of Parliament.

Nancy Astor. / Keystone Features/GettyImages

Nancy Witcher Langhorne was born into an impoverished Virginian family in 1879, but by the time she was 18 her father had made his fortune and she was sent to New York, where she met her first husband, Robert Gould Shaw II. The marriage ended in divorce in 1903, and, at the persuasion of her father, she sailed to Britain at the end of 1904 with her son and sister, Phyllis. Her arrival in London put her in the company of several American-born women who had become the wives of British peers, including Pauline Astor, whose brother, Waldorf Astor, Nancy married on April 19, 1906.

Waldorf was the eldest son of William Waldorf, Viscount Astor. The Viscount gifted them the family home, Cliveden Estate, which they turned into the center of political and literary thought. Like his father before him, Waldorf had an inclination for a career in politics and, with Nancy’s support, he was elected as the Member of Parliament for Plymouth Sutton in 1910. On his father’s death in 1919, he inherited the title of 2nd Viscount Astor and was promoted to the House of Lords, leaving his seat in the House of Commons vacant.

Nancy seized the opportunity the 1918 Parliament (Qualification of Women) Act gave her and ran as the Unionist Party (now Conservative Party) candidate to replace her husband as Plymouth Sutton’s MP. Her victory on November 15, 1919, meant that the first ever female MP to take her seat in the House of Commons was a member of the Astor family. She remained an MP until 1945.

8. John Jacob Astor IV died on RMS Titanic while returning from his honeymoon.

John Jacob Astor IV was the son of the Mrs. Astor, Caroline, and cousin of the 1st Viscount Astor. For much of his early life, he tinkered as an inventor and wrote novels—while still managing to increase the family fortune through real estate, particularly the Waldorf-Astoria Hotel.

In 1910, the 47-year-old millionaire caused a scandal when, five months after his divorce, he began courting the 18-year-old debutant Madeleine Force. The two married on September 10, 1911. The couple then set off on honeymoon, traveling from New York to Bermuda to Egypt and then on to Europe. When Madeline became pregnant during the trip, the couple decided to go home. They boarded the RMS Titanic at Cherbourg, France, on April 10, 1912.

No amount of wealth could save them from the horrific events that unfolded on the night of April 12, 1912, when the liner struck an iceberg and began to sink. Madeline, her maid, and her nurse were all given a place on lifeboat 4, but John was told that he and his valet would have to wait until all the ladies were off the ship before they could be evacuated. Reports claimed that John then helped two women—Ida Hippach and her 17-year-old daughter Jean—into the boat before telling his wife, “You are in good hands and I will meet you in the morning.”

John’s corpse was one of only 333 bodies recovered from the sea. He was brought back to New York and buried in Manhattan, and the gold watch he was found with was given to his oldest son and heir, Vincent, who wore it for the rest of his life. Madeleine gave birth to a healthy son on August 14, 1912, christened John Jacob Astor VI (although he is sometimes incorrectly called John V), who immediately inherited a $3 million trust. Madeleine received his house and a $5 million trust fund, though she lost both after remarrying, as John’s will stipulated that she must forfeit the fortune unless she remained single.

9. John Jacob Astor V won an Olympic gold medal for Great Britain.

After his father, William Waldorf, moved to Britain with his family, John V was raised as an English gentleman. He attended Eton College and Oxford University and excelled at sports, including racquets, a game said to have originated in prisons before becoming popular in the alleys of London. By the early 20th century it had become a game for gentlemen, played in some of the most exclusive schools and clubs where specially built courts could be found.

The 1908 Olympics in London featured a number of sports that are no longer found in the modern games, including running deer shooting, tug-of-war, and Jeu de Paume. Racquets was also included, though only Britain fielded a team; Astor was a member in both singles and doubles. He and his partner, Vane Pennell, played only twice—on April 30 and then May 1—to beat their fellow Brits and win the doubles gold medal. Astor then won a bronze in the singles tournament despite only playing one match.

Astor continued his love of the game and that of its sister-sport, Squash Racquets. In 1922, he followed his sister-in-law, Nancy, into politics as MP for Dover, and, despite losing a leg during World War I, he competed in and won the parliamentary squash racquets championship in 1926 and 1927.

10. The Astors count presidents and monarchs as their relatives.

Marriage in 19th-century New York became a slightly socially incestuous affair. Wealthy and politically ambitious families intermarried to the point that by the end of the 19th century, it was possible to claim kinship with almost everyone else. In 1981, Brooke Astor recalled, “My husband, Vincent, used to say that one of the reasons for the various Astors success was that they always married above themselves! It became a family tradition he said, as later on they married with the Schermerhorns and Willings and Beekmans.”

In politics, the Astors had close ties with the Roosevelt family. In 1844, William Backhouse I’s daughter, Laura, married Franklin Delano, the great-uncle of future President Franklin D. Roosevelt. The family connection continued when, in 1878, Helen Schermerhorn Astor, daughter of The Mrs. Astor, married James Roosevelt, becoming Franklin D. Roosevelt’s sister-in-law. And lastly, Helen’s daughter (also Helen), married Theodore Robinson, the nephew of Theodore Roosevelt.

The English branch of the Astor family, meanwhile, found itself mixing with the aristocracy to the extent that they can count members of the British royal family as their relatives. In 1929, Rachel Spender-Clay, granddaughter of William Waldorf, 1st Viscount Astor, married David Bowes-Lyon, the brother of Elizabeth, Duchess of York and the future Queen Consort of George VI.  The Astor family could now claim kinship with monarchy­—not only was Rachel the sister-in-law of George VI, but her son, Sir Simon Bowes-Lyon, is Elizabeth II’s first cousin.

11. A party given by the Astors helped bring down the UK Conservative government.

William Waldorf Astor II, 3rd Viscount Astor / J. Wilds/GettyImages

Nancy Astor’s son, William Waldorf Astor II, continued the family’s interest in politics by becoming an MP himself. Although he was forced to quit the role in 1952 when he became the 3rd Viscount, he continued to mix in political and social circles at his home on the Cliveden Estate.

In July 1961, William was hosting a party that included John Profumo, the Secretary of State for War, at the same time his friend and osteopath, Steven Ward, was throwing a party elsewhere on the estate. When the two groups mingled at the swimming pool, Profumo met Christine Keeler, a model and friend of Ward’s. The affair that ensued was brief and over by the end of 1961. But unfortunately for Profumo, Keeler was also the girlfriend of another of Ward’s guests, a Soviet Union naval attaché named Yevgeny Ivanov.

By 1963, the affair was becoming public, and whispers were circulating that the three were involved in a spying ring. Profumo made a statement to the House of Commons claiming that “there was no impropriety whatsoever in my acquaintanceship with Miss Keeler,” but by June he was forced to admit the affair and that he had lied to Parliament. While no evidence was ever found that he had passed secrets to Ivanov via Keeler, he resigned his ministerial position.

The Conservative government, under the Prime Minister Harold McMillian, was seriously damaged by the scandal and, unable to recover, they lost the subsequent general election. William was accused of having an affair with one of the other models, Mandy Rice-Davies, and although there was no evidence that he orchestrated the meeting between Profumo and Keeler, he was investigated by the police. His standing was irreversibly damaged and he became a social pariah. When he died of a heart attack in 1966, the Astor family left Cliveden, never to return.