6 of History’s Worst In-Laws

If you thought your in-laws were bad, just wait until you hear about some of these families from the most dysfunctional annals of history.

From your garden-variety overbearing mother-in-law types to brother-in-laws so bad they sent small children to the Tower of London, these famous figures prove that sometimes, marrying into a new family isn’t all it’s cracked up to be. 

1. Ivan the Terrible
2. The 16th Earl of Warwick and Richard III
3. Sara Delano Roosevelt 
4. Herod the Great 
5. King George II and Queen Caroline 
6. Madge Gates Wallace 

Ivan the Terrible

Ivan the Terrible earned his nickname for a few different reasons—turns out, you don’t become the first tsar of Russia by being a nice guy. But not even Ivan’s family could escape his hair-trigger temper or his legendary wrath. 

One of the most brutal and significant examples of this occurred in November 1581. As the story goes, Ivan reportedly fell into a violent rage over his daughter-in-law, Yelena—the wife of his eldest son, Ivan—because he thought her clothes were too revealing. 

She was pregnant, but that didn’t stop Ivan from attacking her, and soon, Yelena suffered a miscarriage. Ivan’s son ran to his wife’s defense, and the fight that broke out between the two Ivans would ultimately end badly for Ivan the Younger. 

His father supposedly struck him on the head with a pointed staff. Ivan the Terrible was said to have “immediately [given] himself up to deep grief” once he realized what he’d done to his son, but it was too late. Ivan the Younger died a few days later. 

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The 16th Earl of Warwick and Richard III

One of the biggest scandals of 15th-century England erupted around 1464 after King Edward IV secretly married Elizabeth Woodville, a widowed mother of two and commoner whose husband had recently died fighting for the Lancastrian cause in the ongoing Wars of the Roses. 

Elizabeth wasn’t popular with her new husband’s Yorkist supporters, including his cousin, Richard “The Kingmaker” Neville, the 16th Earl of Warwick, and Edward’s two younger brothers, Richard and George. Warwick, who had been actively trying to arrange a royal marriage for Edward IV, was outraged by the secret nuptials. The relationship between the cousins soon deteriorated, especially as Elizabeth’s family gained more power and influence at court. 

By 1469, Warwick had defected, soon joining the Lancastrian side of the fight in an effort to depose Edward IV and get rid of the Woodvilles for good. In the ensuing conflicts, Edward IV was taken prisoner, Elizabeth’s father and brother were both executed, and her mother was accused of witchcraft. Elizabeth sought sanctuary at Westminster Abbey and gave birth in November 1470 to her first son with Edward, the future Edward V, as the fighting waged on. 

Though Warwick died on the battlefield in 1471, the problems between the in-laws didn’t die with him. In fact, they got even worse. Following his death in April 1483, his brother Richard, Duke of Gloucester, was made the Lord Protector Richard, Duke of Gloucester, the Lord Protector of the Realm until the end of Edward V’s minority. Instead, Richard seized upon the opportunity that his brother’s sudden death provided, ordering the arrests and swift executions of Elizabeth’s brother, Anthony, and Richard, her youngest son by her first husband, as they traveled toward London to crown the new king. 

Then, Edward V was taken to the Tower of London. By mid-June, Edward V’s younger brother, Richard of Shrewsbury, Duke of York, had joined him there. The Princes in the Tower, as they’d later be known, were 12 and 9 years old at the time, and would never be spotted outside of its gates again. It’s assumed they were murdered.

But a coronation did take place that summer. Their uncle, the Duke of Gloucester, was officially crowned King Richard III at Westminster Abbey on July 6, 1483. To add insult to injury, Elizabeth was actually in Westminster Abbey at that time, having yet again sought sanctuary there. Only this time, she lost far more than she could have imagined. In his first official Parliament of January 1484, Richard III stripped his sister-in-law of all the lands and titles she’d received during Edward IV’s reign. He also had her children declared illegitimate on the grounds that Edward IV had already entered into a pre-contract to marry someone else, meaning his marriage to Elizabeth was never legally valid. 

As awful as her Plantagenet in-laws were, Elizabeth Woodville would ultimately get the last laugh. In 1485, Richard III’s short reign came to a screeching halt at the Battle of Bosworth Field, where he was slain by forces under Henry Tudor, the last Lancastrian claimant to the throne. The newly crowned King Henry VII married Elizabeth and Edward’s eldest daughter, Elizabeth of York, in 1486, a move that definitively put an end to the decades-long Wars of the Roses—and thrust the Tudors, a new dysfunctional royal family, into the spotlight. 

Sara Delano Roosevelt 

The relationship between Eleanor Roosevelt and her mother-in-law, Sara Delano Roosevelt, was never easy. Even though the future first lady was the niece of Theodore Roosevelt and part of the prestigious Oyster Bay branch of the Roosevelt family, Sara didn’t entirely approve of the marriage to her only son, Franklin, and she wasn’t shy about making her feelings known. 

“Franklin gave me quite a startling announcement,” she wrote in her journal after her son revealed the news of his engagement to Eleanor in 1903. Some argue the shock was due to her displeasure with Eleanor. Others argue that she was concerned that the 21-year-old Franklin was too young to get married, especially because he was still in school. Either way, after initially trying to talk him out of it, Sara convinced Franklin to keep the news secret for a year and took him on a Caribbean cruise, all in the hopes that some time apart from Eleanor would change his mind. 

The couple got married anyway on St. Patrick’s Day in 1905, with Uncle TR giving away the bride. Sara’s domineering influence over Franklin wouldn’t let up, though, and trickled into many facets of his family life with Eleanor. She was controlling and opinionated about the couple’s children, frequently criticizing and undermining Eleanor’s parenting decisions. At one point, Sara told the couple’s eldest son, James, “Your mother only bore you. I am more your mother than your mother is.”

Even the couple’s double townhouse on East 65th Street in New York City became an enduring testament to Sara’s grip over the family. She commissioned it in 1906 as a wedding gift for the young newlyweds. The multi-story structure was split into two virtually identical homes that shared the same front entrance and facade. There were also interior sliding doors connecting Sara’s half of the residence to parts of Franklin and Eleanor’s, including one to her grandchildren’s bedrooms on the fourth floor. 

Though Franklin would later describe the townhouse as a place of “happy significance” and “sacred memories,” Eleanor didn’t echo her husband’s sentiments. “It isn’t mine in any way,” she later said. “I had nothing to do with getting it and it isn’t the kind of house I would have got. I hate it.” 

Herod the Great 

History may remember Herod I as The Great, but the Roman-appointed regional king of Judea wasn’t so great when it came to his in-laws—or really anyone in his immediate family, for that matter. 

Soon after marrying his second wife, Mariamne of Hasmonean, Herod became consumed by fear and paranoia that her politically influential family had greater designs on his throne. Though Herod made her brother, Aristobulus, high priest shortly after the wedding in 37 BCE, the appointment was short-lived—as were any illusions about this being a happy marriage. 

Within about a year, Aristobulus drowned under “mysterious” circumstances, and Mariamne was executed in 29 BCE, allegedly for infidelity and plotting to kill the king. Herod didn’t stop there, though. He eventually ordered the executions of Mariamne’s mother, Alexandra the Maccabee, and even two of their sons, all on the grounds of treason. 

And yes, Herod the Great is the one you read about in the Bible. Jesus of Nazareth was born during his reign.

King George II and Queen Caroline 

Royals can have problems with their parents, just like the rest of us. Frederick, Prince of Wales, certainly did: His relationship with his father, King George II of Great Britain, and his mother, Queen Caroline, was notoriously rocky. So much so that when Frederick’s wife, Princess Augusta of Saxe-Gotha, went into labor with their first child in late July 1737, he resorted to some pretty extreme measures to ensure that neither of his parents was present for the birth. 

According to an admittedly anti-Frederick source, the prince insisted that Augusta leave Hampton Court—where his parents and their courtiers lived—and travel 13 plus miles by carriage to St. James’s Palace in London. The journey took over an hour and was reportedly grueling for the young princess, who was actively experiencing labor pains. But the delivery was even worse: No one was expecting them at the palace, so there were no beds or clean sheets available for her. Instead, Augusta was forced to give birth to her daughter on a couple of tablecloths. 

Though she missed the birth, Queen Caroline arrived early the next day at St. James’s Palace. Her indignation over the princess’s late-night flight was reportedly “great.” Still, she claimed that she was happy that the princess had given birth to a “poor little ugly she-mouse” rather than a “large, fat, jolly boy” because it meant it probably was the princess’s child rather than some random baby they’d hired. The circumstances surrounding the birth made the already-frosty relationship between Prince Frederick, his wife, and his parents even colder.

Royal historians are often split between Team Caroline and Team Frederick as to who was worse, but Queen Caroline was the clear winner when it came to brutal insults: Beyond “she-mouse,” she’s also said to have remarked that Frederick was “The greatest ass, the greatest liar, the greatest canaille, and the greatest beast in the whole word. I heartily wish he were out of it” as well as calling him “an avaricious, sordid monster” who would happily sell the crown. 

Madge Gates Wallace 

Harry S. Truman didn’t have the mother of all bad mother-in-laws, but he certainly had an exceptionally overbearing one in Madge Gates Wallace. 

After marrying her daughter, Bess, in 1919, Truman moved into the Wallace family home at 219 North Delaware Street in Independence, Missouri. He was surrounded by in-laws, including Madge and several members of Bess’s family. The Wallace family matriarch didn’t exactly make things easy for the future president of the United States. She repeatedly knocked his family’s background throughout this time, supposedly referring to him as “farmer Truman” (and later as “Mr. Truman”). 

She felt the failed haberdasher wouldn’t amount to much. Madge still wasn’t impressed when Truman became president in 1945. She moved into the White House alongside the Trumans but often questioned her son-in-law’s chops for the role, even expressing support for New York’s Governor Thomas Dewey, Truman’s opponent in the 1948 presidential election. In 1951, Madge also criticized Truman over his highly controversial decision to fire General Douglas MacArthur, questioning why he’d ever fire such a “nice man.”

For his part, Truman seemingly took it all in stride. He was reportedly gracious toward her right up to the very end. After Madge’s death at the White House in 1952, he even wrote in his diary: “She was a grand lady. When I hear these mother-in-law jokes, I don’t laugh. They are not funny to me, because I’ve had a good one.”

This story was adapted from an episode of The List Show on YouTube. Subscribe for new videos every week.