In May, Hillary Clinton floated a proposal: If she was elected president, she would consider naming Bill Clinton as an economy czar responsible for aiding America’s most impoverished communities. The blowback was swift, and within days she had backed off her two-for-one plan.

Bill Clinton is far better-known than Jared Kushner, President-elect Donald Trump’s son-in-law and newly appointed senior adviser. But the speed with which the Bill Clinton trial balloon burst is suggestive: Naming family members to official administration jobs is not just fraught with ethical land mines and legal hurdles. History shows it’s also a recipe for unforeseen headaches and policy controversies, even a disaster waiting to strike an administration.

Kushner’s true problem isn’t the wording of the 1967 anti-nepotism law that may or may not bar his appointment. Nor is the ethical dilemmas that he and his wife Ivanka Trump have courted as they haphazardly disentangle themselves from their business holdings and financial connections with foreign governments and corporations.

The real problem for Kushner — and Trump — is that the politics of nepotism has proven highly combustible and deeply tendentious in the handful of times when presidents have named family members to posts during the past century. And media coverage, deepening partisan polarization and a greater societal emphasis on disclosure by government officials have made such appointments even more fraught politically than they were before.

Kushner, a political cipher of sorts, has such a thin track record of public service that it’s hard for Americans to have much sense of what his convictions are. A trusted adviser to Trump’s campaign, Kushner reportedly was capable of curbing his father-in-law’s worse instincts, helping the candidate navigate his myriad self-inflicted crises. His family ties, his campaign service and his unquestioned devotion to the president-elect appear to be his most outstanding qualifications. And his power in the White House — his access to the Oval Office — is unlikely to be rivaled by anybody.

Yet he and his father-in-law seem to have little awareness of what they are about to step in. The three times in the 20th century when a president appointed a close family member to a formal role had more downsides than upsides. Such appointments undercut the administration’s desired narrative and harmed its reputation. They also sowed discord and courted scandal and handed the president’s fiercest critics a club that they used in effectively assailing the White House. The family appointments more often than not had unintended consequences.

Eleanor Roosevelt’s troubled time as assistant director of the Office of Civilian Defense during the early 1940s is a case in point. Franklin Roosevelt appointed his wife to take charge of volunteer participation in September 1941. Like Kushner, Eleanor Roosevelt refused to take a salary, although she did receive $10 a day for government expenses related to her new agency role. Unlike Kushner, Eleanor Roosevelt had a firm vision — a set of principles to improve American life — that animated her public-spirited life: She wanted to ensure that wartime democracy was economically and socially secure, seeking to enshrine a wartime New Deal as a prerequisite to any national defense program equipped to defeat the Nazis.

In early February 1942, however, newspapers reported that the first lady had put a dancer friend, Mayris Chaney, on the government payroll with an annual salary of $4,600 (which would be more than $68,000 today). Chaney’s job was to teach dancing to children to raise their morale and relieve pressure from air raids. Her tenure came to an abrupt, ignominious end.

The revelation put the first lady at the center of the nation’s first scandal since the attacks on Pearl Harbor. As the story broke, Interior Secretary Harold Ickes confessed to his diary, today, “Hell broke loose.” Members of Congress were outraged: One denounced the administration for playing at a “Roman holiday” while Americans were shedding blood and treasure on foreign battlefields. Gossip columnist Walter Winchell quipped that Congress, though it had voted in favor of “War on the Axis,” was waging war on the first lady.

The scandal not only tarnished the Office of Civilian Defense’s reputation but also cast some early doubts on Roosevelt’s wartime leadership. James Landis, the director of the agency when the scandal erupted, captured the dilemma he faced, saying something that might also resonate with Trump’s incoming Chief of Staff Reince Priebus: Eleanor Roosevelt’s ties to the president, Landis reflected, “[are] considerably closer than mine!” The Roosevelts put Landis in an impossible position as a nominal superior to a much more influential assistant director.

As attorney general during the early 1960s, Robert F. Kennedy became a de facto alter ego to his brother John F. Kennedy, an all-purpose aide-de-camp. U.S. News & World Reports termed him the “Assistant President.” RFK gave advice on U.S. policy toward Cuba, CIA covert operations and civil rights and became a voice of uncharacteristic restraint in meetings during the Cuban missile crisis. Yet his heavy-handed attitude and blind loyalty to his brother — his refusal to brook dissent inside the administration — caused some colleagues to chafe. Some White House aides, historian Jeff Shesol has written, “considered [RFK] an irritant and a micromanager …. Robert Kennedy’s expanding reach and his brusque, if not brutal, manner raised hackles in the White House.”

Though he held enormous sway as the president’s brother, RFK’s advice was not uniformly sound-minded. He urged a “sharp step-up” of U.S. foreign policy in Vietnam and endorsed a highly aggressive program of “espionage, sabotage, general disorder” to topple Cuba’s Castro regime in the wake of the Bay of Pigs fiasco. “Get off your ass on Cuba!” he barked at generals. President Lyndon Johnson’s hatred of RFK has widely been seen as a major impetus for the 1967 anti-nepotism law. And upon his appointment as attorney general, RFK was ridiculed as an undeserving hack, an inexperienced lawyer, and totally unqualified.

For all the headaches he caused, though, Kennedy did prove himself to be an astute politician; he later came to support federal intervention in support of civil rights in the South and ultimately carved his own outsized role as a national political force. There is little evidence that Kushner has any of RFK’s policy chops, political skills or intellectual convictions, however. His true main interest seems to be his support for the election of Donald Trump. He is no Robert Kennedy.

As first lady, Hillary Clinton’s secrecy and hubris as head of her husband’s administration’s health care task force ultimately crippled their goal. Her appointment backfired. Her official role gave GOP critics a chance to paint reform as a complicated behemoth and the first lady’s task force as contemptuous of Congress. Some White House aides saw Hillary Clinton as so powerful, with unparalleled cachet, that they watched in frustration as she and the President dismissed their criticisms of the emerging health reform plan. The first lady’s certainty that the administration’s 1,342-page proposal was the answer led her to blister reform’s critics in politically unhelpful terms. Addressing the American Academy of Pediatrics, the first lady reasoned that insurers didn’t support the goal of universal coverage “because the more they can exclude, the more money they can make.” Emboldened critics of reform derided their plan as “Hillarycare,” and the Democratic-controlled Congress failed to muster the votes to pass it.

History is a flow, of course, and patterns don’t always repeat themselves like clockwork. Just because the Roosevelts, the Kennedys and the Clintons encountered political problems through nepotistic appointments doesn’t ipso facto doom Kushner to automatic disgrace and national opprobrium. But given what happened when the most accomplished political families of the 20th century tried it, Trump and Kushner shouldn’t bank on winning this time, either.