• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
PoliticsDonald Trump

After decades of investigations, Donald Trump may finally face the ‘shocking event’ he has long avoided: criminal charges

By
Jill Colvin
Jill Colvin
and
The Associated Press
The Associated Press
Down Arrow Button Icon
By
Jill Colvin
Jill Colvin
and
The Associated Press
The Associated Press
Down Arrow Button Icon
March 21, 2023, 8:03 PM ET
Former President Donald Trump.
Former President Donald Trump. Phelan M. Ebenhack—The Washington Post/Getty Images

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.

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.

The 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-South Carolina, echoing other GOP officials, who have also argued the probe will likely help Trump in the short term.

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.”

Subscribe to Well Adjusted, our newsletter full of simple strategies to work smarter and live better, from the Fortune Well team. Sign up today.
About the Authors
By Jill Colvin
See full bioRight Arrow Button Icon
By The Associated Press
See full bioRight Arrow Button Icon

Latest in Politics

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Politics

Putin presides over Russia’s Victory Day parade without tanks, missiles and other heavy equipment due to threat of Ukrainian long-range drones
PoliticsRussia
Putin presides over Russia’s Victory Day parade without tanks, missiles and other heavy equipment due to threat of Ukrainian long-range drones
By The Associated PressMay 9, 2026
2 hours ago
Bahrain, which hosts the U.S. Navy’s Mideast HQ, arrests dozens with alleged links to Iran’s Revolutionary Guard
PoliticsIran
Bahrain, which hosts the U.S. Navy’s Mideast HQ, arrests dozens with alleged links to Iran’s Revolutionary Guard
By Adam Schreck, Samy Magdy and The Associated PressMay 9, 2026
2 hours ago
Pedestrian who jumped Denver airport fence dies after being hit by Frontier Airlines plane, sparking an engine fire and forcing passengers to evacuate
North AmericaAirline industry
Pedestrian who jumped Denver airport fence dies after being hit by Frontier Airlines plane, sparking an engine fire and forcing passengers to evacuate
By The Associated PressMay 9, 2026
2 hours ago
As hantavirus outbreak unfolds, the CDC is missing in action, experts say. ‘I’m very sorry to say that we are not prepared’
PoliticsHealth
As hantavirus outbreak unfolds, the CDC is missing in action, experts say. ‘I’m very sorry to say that we are not prepared’
By Mike Stobbe and The Associated PressMay 9, 2026
3 hours ago
You’re probably safe from the Hantavirus outbreak, but here’s what you absolutely must not do, experts say
PoliticsCoronavirus
You’re probably safe from the Hantavirus outbreak, but here’s what you absolutely must not do, experts say
By Catherina GioinoMay 8, 2026
20 hours ago
kid on phone
Politicssmartphones and mobile devices
‘Close to zero’: Schools are spending tens of millions banning phones from classrooms, but test scores aren’t improving
By Jake AngeloMay 8, 2026
23 hours ago

Most Popular

California farmers must destroy 420,000 peach trees after Del Monte closes its canneries and cancels more than $550 million in long-term contracts
North America
California farmers must destroy 420,000 peach trees after Del Monte closes its canneries and cancels more than $550 million in long-term contracts
By Sasha RogelbergMay 7, 2026
2 days ago
A Michigan farm town voted down plans for a giant OpenAI-Oracle data center. Weeks later, construction began
Magazine
A Michigan farm town voted down plans for a giant OpenAI-Oracle data center. Weeks later, construction began
By Sharon GoldmanMay 6, 2026
3 days ago
'Blue dot fever' plagues musicians like Post Malone, Meghan Trainor, and Zayn as a growing list of artists cancel tours due to lagging ticket sales
Arts & Entertainment
'Blue dot fever' plagues musicians like Post Malone, Meghan Trainor, and Zayn as a growing list of artists cancel tours due to lagging ticket sales
By Dave Lozo and Morning BrewMay 7, 2026
2 days ago
Current price of oil as of May 8, 2026
Personal Finance
Current price of oil as of May 8, 2026
By Joseph HostetlerMay 8, 2026
1 day ago
The CEO of Maersk, which ships 14% of everything you buy, said the Iran war is adding $500 million in monthly costs it's trying not to pass down
Energy
The CEO of Maersk, which ships 14% of everything you buy, said the Iran war is adding $500 million in monthly costs it's trying not to pass down
By Sasha RogelbergMay 8, 2026
1 day ago
Airbnb CEO Brian Chesky warns two types of people won’t survive the AI era: ‘pure people managers’ and workers who resist change
Success
Airbnb CEO Brian Chesky warns two types of people won’t survive the AI era: ‘pure people managers’ and workers who resist change
By Emma BurleighMay 7, 2026
2 days ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.