scorecard2022 is shaping up to be a legal nightmare for Trumpworld. Here's a timeline of upcoming court cases and legal obstacles.
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2022 is shaping up to be a legal nightmare for Trumpworld. Here's a timeline of upcoming court cases and legal obstacles.

Jacob Shamsian,Camila DeChalus,C. Ryan Barber   

2022 is shaping up to be a legal nightmare for Trumpworld. Here's a timeline of upcoming court cases and legal obstacles.
Political consultant Roger Stone, former President Donald Trump, and Rep. Matt Gaetz of Florida.Anna Moneymaker/Getty Images; Scott Olson/Getty Images; Greg Nash-Pool/Getty Images
  • Donald Trump and his allies are facing a flurry of legal challenges this year.
  • The New York investigations into his company’s finances are ongoing, as are other lawsuits related to his business and January 6.

Former President Donald Trump has had a number of surprising legal victories ever since he left the White House — though his greatest potential battles are still looming.

In November, Summer Zervos, who had accused Trump of sexual assault following her appearance on "The Apprentice," dropped her lawsuit against him before he was forced to sit for a deposition. At around the same time, a New York state judge dismissed a lawsuit from Michael Cohen seeking to have the Trump Organization reimburse legal fees for illegal work he did on Trump's behalf.

But greater dangers loom. The Trump Organization is the subject of a sprawling investigation from the Manhattan District Attorney's and New York Attorney General's offices into alleged financial misconduct.

In Atlanta, Fulton County District Attorney Fani Willis is weighing charges over his conduct in the 2020 election. Those investigations are proceeding as the Justice Department comes up on the five-year deadline to prosecute Trump over the acts of possible obstruction that former Special Counsel Robert Mueller III scrutinized as part of his investigation into Russia's interference in the 2016 election.

Meanwhile, the Biden administration is sending a steady stream of Trump's White House records to the House committee investigating the January 6 attack on the Capitol. And Trump — along with many of his allies — face political investigations and lawsuits stemming from the January 6 insurrection in 2021. Expect the judges in those cases to set court dates for those cases later this year.

While Trump mulls whether to run for president again in 2024, 2022 is shaping up to be a year of legal headaches for Trump and his associates. Here's a timeline of the threats Trumpworld faces.

January

January
Allen Weisselberg, center, the Trump Organization's chief financial officer, arrives for a courtroom appearance in New York, Monday, Sept. 20, 2021.      AP Photo/Craig Ruttle)

January 31 — A New York state court in Manhattan court will hold a hearing in the criminal case against the Trump Organization and its CFO Allen Weisselberg, who's become more marginalized within the company following the indictment from last July.

The status conference is expected to update the public on how Trump Organization lawyers are reviewing the 6 million pages of discovery material for the case, where the Manhattan District Attorney's office alleges the company and executive dodged millions of dollars in taxes. The judge has also signaled he wants to hold a trial before the end of 2022.

February

February
DC Attorney General Karl Racine speaks during a news conference outside the US Capitol on Tuesday, Dec. 14, 2021.      Bill Clark/Getty Images

February 4 — Trump's lawyers pushed for months in federal courts to keep the Biden administration from turning over his White House records to the House committee investigating the January 6 attack on the Capitol. At every turn, the former president lost, with the Supreme Court effectively rejecting his claim of executive privilege.

Now, with the National Archives and Records Administration already turning over documents, Trump is facing a decision of how — or whether — to proceed with his legal challenge.

An answer could come in early February. Just days after the Supreme Court declined to take up Trump's case, lawyers for the House and Biden administration asked to have until February 4 to make their latest response to the former president's legal arguments.

In light of the Supreme Court decision and subsequent product of records to the House committee, the lawyers said they had agreed that the best course was to extend the deadline so that Trump "can determine his next steps."

February 17 — A Washington, DC, court is set to hold a hearing on the DC Attorney General's lawsuit against Donald Trump's 2017 inaugural committee. In November, Trump notched a partial win as the judge dismissed part of the suit, but other elements of the case — where the attorney general's office alleges the committee illegally misused funds — will be moving forward. The hearing is expected to set a schedule for the discovery process before it goes to trial.

March

March
Rep. Matt Gaetz, a Republican of Florida.      Caroline Brehman/CQ-Roll Call/Getty Images

March 29 — Joel Greenberg, a former associate of Rep. Republican Matt Gaetz of Florida, is expected to go before a judge for his prison sentencing. Greenberg could potentially be a key witness in the Justice Department investigation into the lawmaker.

The Gaetz associate has already pleaded guilty to several charges, including sex trafficking. Gaetz is one of Trump's most loyal supporters.

April

April
Former President Donald Trump arrives at Trump Tower in Manhattan on August 22, 2021, in New York City.      James Devaney/GC Images

April 4 — The second special grand jury empaneled by the Manhattan District Attorney's office in its criminal investigation into the Trump Organization's finances is set to wrap up by this date. Another indictment in the investigation — or decision from prosecutors to not indict — could come shortly afterward.

May

May
Then President-elect Donald Trump boards the elevator at Trump Tower in New York City on January 16, 2017.      Dominick Reuter/AFP via Getty Images

May 2 — Jury selection is scheduled to begin for a trial for a civil lawsuit brought by a group of protesters against the Trump Organization. The protesters sued in 2015, alleging the company's security guards roughed them up during a demonstration outside Trump Tower. A video of a deposition Trump was forced to take this past fall is expected to be shown at the trial as evidence.

May 2 — A special grand jury for Fulton County District Attorney Fani Willis's investigation into Trump will be impaneled on May 2 and continue for up to 12 months. This announcement on Monday comes after Willis formally requested to have a special grand jury that would give her the subpoena power to obtain documents and compel witnesses to testify.

June

June
Fulton County District Attorney Fani Willis walks past boxes filed with criminal cases at her office Wednesday, Feb. 24, 2021, in Atlanta.      AP Photo/John Bazemore

June 1 — Fulton County District Attorney Fani Willis told the Associated Press in January that she is expecting to decide whether to charge Trump by the first half of 2022.

June 29 — Litigants will get to see a copy of Trump's "Celebrity Apprentice" tapes. June 29 marks the deadline of discovery in a lawsuit brought by a group of people who say the Trump Organization pushed an alleged pyramid scheme.

While Trump, in "Celebrity Apprentice," vouched for the ACN Videophone, litigants are trying to figure out if other footage shot for the show demonstrated otherwise. ACN lost an attempt to bring the case to arbitration, and a jury trial is expected to be scheduled for late 2022 or 2023.

July

July
Steve Bannon waves after speaking to the press on his way out of federal court on November 15, 2021 in Washington, DC.      Drew Angerer/Getty Images)

July 7 — Prosecutors and Roger Stone, one of Trump's longtime political advisors, have to meet this deadline for a criminal case where prosecutors allege Stone failed to pay millions in taxes.

July 18 — Former White House chief strategist Steve Bannon is expected to go to court in Washington, DC. Bannon is facing two criminal charges over defying a congressional subpoena. The Justice Department formally charged him in November 2021 after he refused to comply with a subpoena handed down from the House Select Committee that is investigating the January 6 riot.

November

November
Trump ally Roger Stone is auctioning off a non-fungible token of an autograph addressed to him by former President Donald Trump.      Stone Cold Collection/Roger Stone

November 7 — Trump's longtime political advisor Roger Stone is scheduled to go to trial in federal court in Florida over allegations that he failed to pay more than $2 million in taxes.

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