United States elections raise an individual to the presidency. In doing so they elevate an entire family to new heights of prominence – children included.

Sometimes that works out great. The kids are too young to be trouble, or they are dedicated to their own principles of public service. Think of John Eisenhower, the son of Dwight Eisenhower who became an Army brigadier general and military historian; or Caroline Kennedy, the daughter of John F. Kennedy and current ambassador to Japan.

But things don’t always go well. Adult children have been trials, distractions, and/or political problems for presidents since the dawn of the republic. Their personal relationships become tawdry. Their educational attainments are nil. Their business careers appear to trade on White House connections.

Enter President-elect Donald Trump’s oldest kids, Donald Jr., Eric, and Ivanka. In some important ways, the controversies generated by their relationship to their dad and his companies are new. In others they aren’t.

“My children give me more pain than all my enemies,” wrote President John Adams in 1798, irritated by family demands for federal largess.

The (very) good and the (very) bad

The Adams family alone may encapsulate the positive and negative aspects of the prominence and opportunity that falls to the children of a US president.

The positive involved one of Adams's most controversial decisions. In 1797, he appointed his son John Quincy Adams as American minister to Prussia. The son objected, foreseeing – rightly – that critics would charge the appointment was nepotism and that the father was grooming a presidential heir.

But the Harvard-educated John Quincy was highly qualified, and his astute dispatches helped the US avoid a war with France. Later, he served as secretary of State and president in his own right.

However, Adams’s two younger sons were conspicuous failures. Both drank heavily and failed at virtually all employment they tried.

“The question of how two of his sons, Charles and Thomas, could have so sadly fallen by the wayside, while John Quincy so conspicuously excelled could only have weighed heavily on Adams’s mind,” wrote historian David McCullough in his Adams biography.

The daughter who won over Japan

Sometimes presidential children, like presidents, grow in office. They start out like liabilities, but end up useful, even iconic on their own.

That describes Alice Roosevelt Longworth. A debutante when her father, Theodore Roosevelt, became president following William McKinley’s assassination, the beautiful Alice was a handful. She smoked in public, learned the hula, and was prone to firing off occasional fusillades with her pocket revolver.

But her father grew to appreciate her ability to attract and channel attention while speaking her own mind. In 1905, he sent her on a lengthy US government tour of Asia. She was a wild success.

“When they arrived in Tokyo on 25 July, Alice dazzled the Japanese to such an extent that the Congressional wives might just as well not have disembarked,” wrote historian Edmund Morris in his Teddy Roosevelt biography.

The goodwill she engendered facilitated Roosevelt’s brokering the end of the Russo-Japanese War at a Portsmouth, N.H., conference. He won the Nobel Peace Prize for his efforts. Alice developed into a famous – and famously waspish – Washington presence.

The son who cashed in on the presidency

Business interests have always been drawn to presidential children – and vice versa. The former see an easy means of gaining influence, the latter a way to make large sums of money in short periods of time.

Controversy can result. That’s not new to the incoming Trump administration. Take James Roosevelt, President Franklin Roosevelt’s eldest son, who had his own problems with this issue.

James never quite earned his degree from Harvard, falling a few classes short. Denied entry to Harvard Law School, he got into Columbia Law, but left school after a year.

Shortly after his father won the presidency in 1932, he joined Democratic financier Joseph Kennedy on a cruise to England. James helped organize an audience with Prime Minister Winston Churchill at which Kennedy lobbied for an exclusive franchise to distribute British liquor brands in the US following the repeal of Prohibition.

Long story short, Kennedy won the deal, and James made money by writing insurance on the shipments. Ultimately, word got back to his father and the son had to curtail some of his business activities.

“Jimmy seemed clueless about the political embarrassment the British liquor deal might cause his father if it became public,” wrote historian Thomas Maier in a book on the relationship between the Kennedy and Roosevelt families.

In the end, neither James nor his three younger really lived up to their name, and all showed an “astonishing” lack of sensitivity about using their father’s influence to make money, according to a family friend quoted in historian Doris Kearns Goodwin’s book on Franklin and Eleanor Roosevelt.

“The boys disappointing careers and broken relationships (between the four of them there would be eighteen marriages) devastated Eleanor,” writes Goodwin.

How Trump's family is different

There have been signs of similar friction between President-elect Trump and his two sons. In part that may be because he divorced their mother Ivana.

Trump’s dealings with daughter Ivanka seem smoother. She appears set to fill some first lady duties in the Trump administration.

Yet already Trump is involved in an uproar over the continued involvement of his children in the presidential transition and the family business. The most recent incident involved all three sitting in on his meeting with Silicon Valley business leaders on Wednesday.

His children are all vice presidents of the Trump Corp. and the sons, at least, plan to remain so after Trump takes office. Trump has said he’ll transfer control of his businesses to the kids, but it’s not clear yet exactly what he means by that.

The big difference with some past examples here is that Trump approves of the arrangement and is directing it. He also would profit from any actions they take. That’s drawn some scathing criticism.

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Susan Hennessey, a Brookings Institution fellow and editor at the national security legal blog Lawfare, tweeted:

Trump's kids had zero business in that meeting. This is intentional attempt to try to normalize their grotesque conflicts. It is not okay. https://t.co/3CgBM2pH4Q — Susan Hennessey (@Susan_Hennessey) December 14, 2016

At a panel hosted by Democrats on the House Government Oversight Committee earlier this week, Norm Eisen, who served as President Obama’s ethics lawyer, said the proposed Trump arrangement risks creating “princelings” – a term that refers to the offspring of officials in China who serve as middlemen for business deals.

“They’re used as a conduit to influence the leader,” Mr. Eisen said. “[Trump] needs to make a clean break, not just on operations, but on interest.”