Trump faces more indictments, fines and possible jail time as legal troubles mount

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As Donald Trump looks to secure the Republican presidential nomination and win a second White House term, he will also have to navigate a legal minefield that could include as many as four criminal indictments and at least two civil cases.

While a losing verdict in the civil cases would mean Trump could be required to pay millions of dollars in damages, being found guilty in the coming criminal ones could result in jail time. That certainly could impact his ability to wage a campaign for president or to serve in that capacity for a second term.

Former President Donald Trump points toward the audience as he speaks at a podium.
Former President Donald Trump at the Turning Point Action Conference in West Palm Beach, Fla., on July 15. (Marco Bello/Reuters)

Here's where things stand:

Classified documents indictment

Aileen Cannon speaks remotely during a Senate Judiciary Committee oversight nomination hearing.
Aileen Cannon speaks remotely during a Senate Judiciary Committee hearing on her nomination as a U.S. District Court judge in July 2020. (U.S. Senate via AP)

Scheduled start date: May 20, 2024

In June, Trump was arraigned on 37 felony counts stemming from his handling of classified documents after leaving the White House. He pleaded not guilty.

If a Florida jury finds Trump guilty of the charges against him, he almost certainly will face the prospect of a prison sentence, but the duration of that will be decided by Judge Aileen Cannon, a Trump appointee who has issued rulings in the matter favorable to the former president. But Cannon also denied a motion by Trump's lawyers to move the trial until after the 2024 election.

New York hush money indictment

Stormy Daniels attends the Exxxotica Expo.
Stormy Daniels attends the Exxxotica Expo on April 22 in Rosemont, Ill. (Jacek Boczarski/Anadolu Agency via Getty Images)

Scheduled start date: March 25, 2024

In April, Trump pleaded not guilty to 34 felony counts of falsifying business records stemming from a hush money payment made to porn star Stormy Daniels during the 2016 presidential campaign to keep her from revealing their alleged extramarital affair.

The felony charges brought by Manhattan District Attorney Alvin Bragg of falsifying business records carry a maximum prison sentence of four years, and if Trump is convicted of all 34 counts, he could, in theory, see as much as 136 years behind bars. Most legal experts say that even if he is found guilty of all the charges, such a sentence is unlikely.

Looming Jan. 6 indictment

Violent insurrectionists loyal to then-President Trump storm the U.S. Capitol.
Violent insurrectionists loyal to then-President Trump storm the U.S. Capitol on Jan. 6, 2021. (John Minchillo, File/AP)

Last week Trump revealed that he had been sent a "target letter" by special counsel Jack Smith notifying him that he was the subject of a possible criminal investigation into the Jan. 6, 2021, riot at the U.S. Capitol and the efforts to illegally overturn the results of the 2020 election.

Target letters often indicate that criminal charges are imminent, and in this case they are likely to include obstruction of an official proceeding, conspiracy to defraud the United States and insurrection, all of which carry potentially hefty prison sentences upon conviction.

Possible Georgia election interference indictment

Fulton County District Attorney Fani Willis poses for a portrait in front of filled bookshelves.
Fulton County, Ga., District Attorney Fani Willis on April 19 in Atlanta. (Brynn Anderson, File/AP)

Fulton County District Attorney Fani Willis has indicated that criminal charges against Trump could be filed as soon as next month relating to his efforts to overturn the 2020 election results in Georgia.

Willis is said to be readying racketeering charges against Trump that involve witness tampering and computer crimes in an effort to convince state election officials to flip the election results in the battleground state in his direction. Trump's lawyers have asked two Georgia courts to disqualify Willis's investigation prior to charges being filed. Last week Georgia's Supreme Court refused to do so. In Georgia, a conviction on racketeering charges carries a minimum prison sentence of five years and a maximum of 20.

E. Jean Carroll civil case

E. Jean Carroll, smiling, walks out of federal court.
E. Jean Carroll walks out of federal court in Manhattan on May 9 in New York. (John Minchillo, File/AP)

Scheduled start date: Jan. 15, 2024

Last week a federal judge rejected Trump's request for a new trial in the sexual abuse and defamation case brought by writer E. Jean Carroll, and refused to lower the $5 million in damages awarded to Carroll by a jury.

Following the initial verdict in May in a case that centered around Trump's alleged sexual assault of Carroll in a New York department store, Trump appeared on a CNN town hall and promptly repeated many of the inflammatory claims he had made against Carroll. In response, Carroll added new defamation charges and is seeking another $10 million from the former president.

Trump Org. fraud civil case

New York Attorney General Letitia James stands at a podium.
New York Attorney General Letitia James at a ceremony in June 2022 in New York. (Mary Altaffer, File/AP)

Scheduled start date: Oct. 2, 2023

New York Attorney General Letitia James has filed suit against the Trump Organization, alleging that the company and members of the former president's family cooked the books, lying to lenders and insurers about the value of real estate assets in order to obtain favorable terms.

While Donald Trump, his sons Eric and Don Jr. and his daughter Ivanka were all named in James's $250 million suit, a judge dismissed the claims against Ivanka Trump in June.