It was 1972 and Donald Trump and his father, Fred Trump, were investigated for discriminating against black renters at their apartments in New York.
The Justice Department sued the Trumps who bitterly fought it for two years until they reached a settlement with no admission of guilt.
The only concession to prosecutors was that the Trumps had to run newspaper advertisements saying that black people were welcome at their properties.
It was the closest brush that Mr Trump has personally had with the law until Tuesday, when he is expected to surrender before a judge on business fraud charges related to a hush money payment to ex-porn star Stormy Daniels.
It will be a historic day as he will become the first US president in history to be charged with a crime.
But for others, it represents a moment that has been overdue for far too long: Donald Trump is finally being held to account.
For decades, Mr Trump has lived with impunity despite a slew of investigations into him and his businesses.
His ability to dodge the consequences of his actions has gradually become part of his brand, such as bragging during a 2016 presidential debate with Hillary Clinton that paying little or no taxes showed he was “smart”.
The idea of that coming to an end may well explain why the Trump family are angry and “rattled”, according to The New York Times reporter Maggie Haberman, who has covered the Trumps in more depth than any other reporter.
The previous cases against Mr Trump and The Trump Organization, his real estate business, show just how extraordinary it is that this will be his first time being arraigned on criminal charges.
The housing discrimination case gave Mr Trump a playbook for how to handle the law: ignore it or delay and attack if backed into a corner
In 1979, while building Trump Tower, he employed non-union Polish immigrants paid as little as $4 an hour who worked seven days a week and slept at the construction site.
Mr Trump dodged prosecution in the early 1980s when prosecutors examined whether he gave three apartments in Trump Tower to associates of the Mob.
During the 1990s, regulators in New Jersey investigated Mr Trump’s casinos and found they could not be considered “financially stable”, yet he continued operating them.
Prosecutors spent years following a similar trail and eventually fined Mr Trump $10m in 2015 for failing to enact anti-money laundering controls at the Taj Mahal casino in Atlantic City, New Jersey.
Mr Trump refused to divest his business interests when he became president in 2017, instead passing control to his son, Eric.
In 2018, a court approved a $25m settlement to 5,000 victims of “Trump University” which promised to teach them how to make a fortune in real estate. Mr Trump was found personally liable.
Then there were the two impeachments whilst he was president, the first of which was for soliciting foreign interference in the US election. The second was over the 6 January, 2021 insurrection at the US Capitol but he survived both after a trial in the Senate rather than a criminal court.
Mr Trump survived the Mueller inquiry into his dealings with Russia as Special Counsel, Robert Mueller, did not recommend charges since he was a sitting president.
Then in December last year, The Trump Organization was found guilty on all counts in a tax fraud trial that saw its chief financial officer jailed for five months, a sentence he is currently serving.
Mr Trump was not personally charged, though his name was invoked throughout the trial.
Running for and winning the presidency has brought unprecedented scrutiny to Mr Trump’s businesses and threw down a gauntlet for prosecutors which is being taken up by the Manhattan District’s Attorney’s office, which is overseeing the hush money case.
But that is far from Mr Trump’s only outstanding legal peril.
Later this month in New York, he faces a defamation case from a journalist who claims he raped her at a department store in Manhattan in the 1990s.
Mr Trump is being investigated in Georgia for alleged interference in the 2020 election and a special counsel is mulling charges over him illegally retaining classified documents after leaving office.
If the former president manages to dodge all of these cases, it will be his greatest escape act yet.