For 40 years, former President Donald Trump has navigated countless legal investigations without ever facing criminal charges. That record may soon come to an end.
Trump could be indicted by a Manhattan grand jury as soon as this week, potentially charged with falsifying business records connected to hush money payments during his 2016 campaign to women who accused him of sexual encounters.
It’s one of several investigations that have intensified as Trump mounts his third presidential run. He has denied any allegations of wrongdoing and accuses prosecutors of engaging in a politically motivated “witch hunt” to damage his campaign.
An indictment in New York would mark an extraordinary turn in American history, making Trump the first former president to face a criminal charge. And it would carry tremendous weight for Trump himself, threatening his long-established ability to avoid consequences despite entanglement in a dizzying number of cases.
Indictment, says biographer Michael D’Antonio, would be a “shocking event, both because of the fact that a former president is being indicted for the first time, but also because one of the slipperiest people at the highest level of business, whose devotion to abusing the system is so well established, is being caught.”
“Throughout his life, he has done things for which he could have been investigated and potentially prosecuted and learned from those experiences that he could act with impunity,” he said.
Trump first faced legal scrutiny in the 1970s when the Department of Justice brought a racial discrimination case against his family’s real estate business.
Trump and his father fiercely fought the suit, which accused them of refusing to rent apartments to black tenants in predominantly white buildings. Testimony showed that applications filed by prospective black tenants were marked with a “C” for “colored.” Trump counter-sued for $100 million, accusing the government of defamation.
The case ended with a settlement that opened the way for some black tenants but did not force the Trumps to explicitly acknowledge they had “failed and neglected” to comply with the Fair Housing Act.
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Since then, Trump and his businesses have been the subject of thousands of civil lawsuits and numerous investigations. There have been probes into his casino and real estate dealings, allegations of bribery and improper lobbying, fraud allegations against the now-defunct Trump University and charitable Trump Foundation and a probe by the Manhattan district attorney into sales at the Trump SoHo hotel-condominium in Lower Manhattan.
Indeed, according Citizens for Responsibility and Ethics in Washington, a government watchdog group abbreviated CREW, as of November 2022, Trump had been accused of committing at least 56 criminal offenses since he launched his campaign in 2015, not including allegations of fraudulent business dealings. But he has never been formally indicted.
Trump is a master of delay tactics, “finding ways to endlessly delay in the hopes that the investigation and litigation will go away. And he’s had remarkable success,” says CREW president Noah Bookbinder, a former federal corruption prosecutor.
“It makes accountability absolutely essential because we can’t have people in a functioning democracy operating in positions of power with total impunity where they can commit crimes and never have to face any consequences,” he said.
Trump’s retort to such strong talk: He commits no crimes, so consequences would themselves be unjust.
As president, Trump continued to face legal scrutiny. For two years, the Justice Department investigated his 2016 campaign’s ties to Russia. While special counsel Robert Mueller never found direct evidence of collusion, his final report did lay out evidence for obstruction. He noted that, because of a department opinion that bars indicting a sitting president, he couldn’t recommend Trump be criminally charged, even in secret.
Since Trump left office, the investigations have circled ever closer.
In January, his namesake company was fined $1.6 million for tax crimes, including conspiracy and falsifying business records. The company’s longtime executive, Allen Weisselberg, is currently serving jail time as punishment for dodging taxes on job perks.
Additional cases are still being pursued. In Georgia, Fulton County District Attorney Fani Willis has been investigating whether Trump and his allies illegally meddled in the 2020 election. The foreperson of a special grand jury, which heard from dozens of witnesses. said last month that the panel had recommended that numerous people be indicted, and hinted Trump could be among them. It is ultimately up to Willis to decide whether to move forward.
In Washington, Trump is under scrutiny from special counsel Jack Smith for his handling — allegations say mishandling — of classified documents after leaving office, as well as for his much-publicized efforts to stay in power, despite his 2020 election loss. Justice Department lawyers in the documents probe have said they have amassed evidence of potential crimes involving Trump’s retention of national defense information as well as potential efforts to obstruct their work.
Some legal experts have questioned the wisdom of having the Manhattan case be the first brought against Trump, when more serious charges could be looming. Trump is expected to be charged with falsifying business records, a misdemeanor unless prosecutors can prove it was done to conceal another crime. And the case dates back years.
“Clearly it’s not the cleanest criminal case that could be brought of all of them that are existing right now,” said Michael Weinstein, an attorney and former Justice Department prosecutor, who said Trump would likely use its potential weaknesses to his political advantage.
“By this case coming first, it gives him a opening to go on offense and attack, which for him is the only way he knows,” Weinstein said.
Still, he said the possible charges felt like a natural culmination of the “unbelievable array of investigations” the former president “has lived through and battled for the last 40 years.”
“There’s a history and pattern of him saying and doing things without resulting in any consequences,” Weinstein said. “After 40 years, do the criminal chickens come home to roost? He’s been fighting a long time, and it could be in the next 12 months he’s facing two or three criminal cases that carry serious criminal liability for him.”
The New York case involves payments made by Trump’s former lawyer, Michael Cohen, who served prison time after pleading guilty in 2018 to federal charges, to porn actor Stormy Daniels and model Karen McDougal. Cohen was reimbursed by Trump, whose company logged the reimbursements as “legal expenses.”
Politically, Trump allies believe the case actually will benefit the former president in the short term by energizing his base in a competitive Republican primary, and would provide another boost later on if it ultimately fails to yield a conviction.
“The prosecutor in New York has done more to help Donald Trump get elected,” says Sen. Lindsey Graham, R-S.C., echoing other GOP officials, who have also argued the probe will likely help Trump in the short term, even if it could prove damaging in a general election.
An indictment wouldn’t stop Trump from continuing his campaign. There is no prohibition against running while facing criminal charges — or even following conviction. Indeed, convicted felons have run for president before, including from behind bars.
“It boggles the mind to think that we have an ex-president on the eve of being indicted still the frontrunner for the Republican Party in 2024,” says presidential historian Douglas Brinkley. “You would have thought (potentially) being arrested would have been a disqualifying factor in presidential politics. But Trump constantly surprises people by his devious and inappropriate behavior that he transcends by turning it into being a victim of a witch hunt.”