If the day-to-day dynamics within most presidential families are a mystery, the public expectations surrounding presidential children are not. Americans have often expressed concern, disdain, or anger when the sons of presidents step out in public to become political players. These fears are as old as the republic, and they strike at the heart of what Americans believe that republic should be.

It’s not that presidential sons have necessarily behaved worse than presidential daughters. Instead, the conventional roles of men and women have often created the circumstances where presidential sons could more easily appear as agents of corruption, while presidential daughters could become symbols of honesty and of love. And the age of those children is crucial. Even as Trump rediscovers the political pitfalls of adult children, presidents have often found a political advantage in their children so long as those children were young.

These issues were clear from the moment there was a presidency. George Washington had no children of his own, and the two stepchildren he acquired from his marriage to Martha Custis died before Washington’s inauguration in 1789. Yet even the absence of children was a matter of importance. After all, the presidency was established as an expressed rejection of monarchy, an institution where children were supposed to play an important (if not always clear) role within in the political order. The fact that Washington had no children further assured Americans of Washington’s promise that he would surrender power rather than create a dynasty.

It was left to Washington’s successor, John Adams, to encounter both the opportunities and the challenges of presidential children. His oldest son, John Quincy, became the sixth President of the United States. The younger Adams had a long public career, but he was always dogged by criticism that his elevation to the presidency smacked of unfair privilege. Two centuries later, George W. Bush, a man very different from John Quincy Adams but also the son of a deposed one-term president, would face very similar criticism that he had only reached the presidency through his name and his father’s influence.

John Quincy Adams and George W. Bush demonstrate the continuities over time. Presidents have long struggled to find an appropriate public relationship with their ambitious adult sons. But the role of presidential children became more pressing during the second half of the 20th century. Presidents increasingly put their private lives on public display, and journalists eventually lost their reticence about exploring those private lives, often because they questioned the image of domestic tranquility that so many presidents sought to create.

Many presidential children have managed to achieve private success and avoid public controversy. They tend to remain anonymous. Instead, it’s the sons who embarrass their families who gain reputations. Before critics lamented the rise of President George W. Bush, they described him as the ne’er-do-well son of George H.W. Bush. Ronald Reagan’s two sons, half-brothers Ron and Michael, would both become the subject of rumors that they had dysfunctional relationships with their parents or with each other.

These varied, occasionally troubled experiences for the adult sons of presidents stand in marked contrast to the role of adult daughters, who have usually enjoyed both greater privacy and a more effective public role supporting their fathers. While presidential sons were often in the public eye, few presidential daughters have shared that spotlight. Thomas Jefferson’s daughter, Martha, may have periodically assumed the role of de facto First Lady for her widower father, but she was the exception that proved the rule.

It was the greater disclosure of presidents’ private lives in more recent decades that would change this, in the process revealing the political value of presidential daughters. Lyndon Johnson and Richard Nixon each came to office with two daughters entering young adulthood. Although they rarely assumed public roles for themselves, they helped humanize their fathers. Lynda Bird Johnson and Tricia Nixon were both married in the White House. These were indeed important private moments for the Johnson and Nixon families. Nonetheless, they were also widely publicized as major public events, representing two presidents as caring fathers rather than pragmatic politicians.

While presidential daughters have played an important role enhancing the image of their fathers, they are nothing compared to young presidential children. The challenges now facing President Trump and the extended Trump family are only heightened by the children who most recently occupied the White House. For the past quarter-century, presidential children consisted exclusively of young girls situated in loving, supportive relationships with their parents. Chelsea Clinton, the Bush twins Barbara and Jenna, and Malia and Sasha Obama all enjoyed the privacy afforded to young presidential children, yet they were never entirely out of the public eye. They made their fathers appear more sympathetic and the presidential family more like a typical American family.

Bill Clinton, George W. Bush, and Barack Obama were only walking in the footsteps of John Kennedy, the president who most effectively deployed his young children to send a message. Whether it was John, Jr. hiding under his father’s desk or Caroline sailing with her father, the Kennedy children were crucial figures in the effort to establish a specific image for Kennedy.

Trump could learn a lot from Kennedy. Trump has an unusual family consisting of five children from three marriages. Twenty-three year-old Tiffany has eschewed most public appearances. The youngest of Trump’s children, eleven year-old Barron Trump, moved into the White House last month. Trump could contribute to a reimagined Trump image: more accessible, more familiar, and seemingly more similar to average American families. But Barron is now—and likely will remain—overshadowed by Donald, Jr., Eric, and Jared Kushner: grown men who have already resuscitated all the fears of presidential children.

And that leaves Ivanka Trump, who reveals as much as anyone about the political role of presidential children. She has faced her own criticism. Critics have emphasized the gender double-standard at work here, and rightly so. Yet there’s more at work than antifeminist agitation. By proclaiming her role as business leader and policy advisor, she has entered a politically dangerous world that had previously been occupied exclusively by presidential sons. And presidential sons haven’t fared much better. Look no further than her brother and her husband.

The big question this week is whether the smoke surrounding Donald Jr. and Kushner will generate fire. Even if it doesn’t, Trump faces the same bind as his predecessors. He has demonstrated the value he places on loyalty, and like most presidents, he considers nobody more trustworthy than family. But that trust can rebound to damage a presidency.

No president in modern times has invested his children—whether his sons, his daughter, or his son-in-law—with so much power. The deck is already stacked against that arrangement helping his presidency. And the events over the past weeks have shown just how much damage it can cause.

Peter Kastor is a Professor of History and American Culture Studies and Chair of the Department of History at Washington University in St. Louis.