Trump’s Former Chief Financial Officer Pleads Guilty to Perjury, Adding Pressure Ahead of Criminal Trial

NEW YORK — Alan Weisselberg, the longtime chief financial officer of the Trump Organization, pleaded guilty on Monday to felony perjury charges in a Manhattan courtroom, admitting that he lied under oath during testimony related to Donald J. Trump’s civil fraud case.

The plea marks the second criminal conviction for Mr. Weisselberg, once one of Mr. Trump’s most trusted lieutenants, and comes at a critical moment as the former president prepares to stand trial in a separate criminal case brought by the Manhattan district attorney.

Prosecutors say Mr. Weisselberg falsely testified about Trump’s asset valuations, which were central to the civil fraud case in which a New York judge found that Mr. Trump and his company had systematically exaggerated the value of properties to obtain favorable loans and insurance terms.

Under the plea agreement, Mr. Weisselberg faces up to five months in jail. He previously served three months at Rikers Island after pleading guilty in 2022 to multiple tax fraud charges connected to the Trump Organization.

A Key Insider Admits Lying Under Oath

For decades, Mr. Weisselberg was the financial gatekeeper of Mr. Trump’s business empire. He oversaw financial statements, worked closely with accountants and banks, and had intimate knowledge of the former president’s wealth claims.

In court, Mr. Weisselberg admitted that during sworn testimony he knowingly gave false answers about asset valuations that prosecutors say were inflated. Those statements were made under oath during proceedings tied to the civil fraud case brought by New York Attorney General Letitia James.

“This was not a misunderstanding,” prosecutors said in court. “This was a deliberate falsehood.”

Legal analysts say the significance of the plea lies less in the sentence and more in what it reveals: a senior executive acknowledging criminal conduct to protect the financial narrative of the Trump Organization.

“This is not a low-level employee,” said a former New York prosecutor. “This is the person who knew the books better than anyone.”

Implications for the Criminal Case Against Trump

The guilty plea comes just weeks before Mr. Trump is scheduled to face trial in Manhattan on charges that he falsified business records related to hush money payments during the 2016 presidential campaign. That case, brought by District Attorney Alvin Bragg, centers on whether those payments were disguised to conceal their true purpose.

In an analysis published Monday, The New York Times noted that Mr. Weisselberg’s plea could strengthen the prosecution’s position.

One reason is deterrence. Prosecutors believe the plea sends a message to other potential witnesses that false testimony will be punished.

Another is credibility. Mr. Weisselberg has long been viewed as a problematic witness because of his prior convictions and loyalty to Mr. Trump. If he does not cooperate, prosecutors can use his perjury conviction to undermine any testimony he might offer in Mr. Trump’s defense.

Mr. Weisselberg was also involved in discussions with Michael Cohen, Mr. Trump’s former lawyer, about structuring hush money payments. Mr. Cohen is expected to be a central witness in the upcoming trial.

A Pattern of Legal Exposure

Mr. Weisselberg’s legal troubles mirror broader findings about the Trump Organization. In the civil fraud case, the judge concluded that Mr. Trump and his company engaged in persistent fraud by overstating asset values.

The court barred Mr. Trump from running a New York business for several years and imposed significant financial penalties.

While the civil case did not directly involve criminal perjury charges against Mr. Trump, Mr. Weisselberg’s admission that he lied under oath about the same financial statements has renewed scrutiny of sworn testimony given by Mr. Trump himself in various legal proceedings.

Judges in past cases have questioned Mr. Trump’s credibility, pointing to inconsistencies between his statements and documentary evidence. Fact-checkers and legal analysts have identified repeated discrepancies in his sworn testimony related to wealth, business dealings, and knowledge of key events.

Why Perjury Matters

Perjury is treated seriously under New York law because it strikes at the integrity of the judicial system. A conviction requires proof that a witness knowingly made a false statement under oath about a material fact.

“Courts depend on truthful testimony,” said a law professor at Columbia University. “When senior executives admit to lying under oath, it undermines confidence in the entire process.”

Unlike complex financial crimes, perjury cases are often more straightforward. Prosecutors compare sworn testimony with documents and other evidence to determine whether a false statement was intentional.

Mr. Weisselberg’s plea establishes that at least one senior Trump Organization executive crossed that line.

A Culture Under Scrutiny

The fact that Mr. Weisselberg has now pleaded guilty twice for conduct tied to his work at the Trump Organization has intensified scrutiny of the company’s internal practices.

Prosecutors in earlier cases described a culture in which executives received untaxed compensation and manipulated records to benefit the company and its owner.

Defense lawyers for Mr. Trump have argued that any wrongdoing was isolated or the result of misunderstanding accounting rules. But legal experts say repeated convictions of top executives make that argument harder to sustain.

“When the same senior figure keeps committing crimes in the course of his job, it raises questions about whether the behavior was systemic,” said a former federal prosecutor.

What Comes Next

Mr. Weisselberg has not agreed to cooperate with prosecutors as part of the perjury plea, according to people familiar with the matter. However, his conviction ensures that any future testimony he gives will be viewed with skepticism by judges and juries.

For Mr. Trump, the plea adds to a growing list of legal challenges. He is already a convicted felon in New York, faces ongoing appeals, and remains under investigation in other jurisdictions.

The perjury conviction does not directly implicate Mr. Trump in new criminal charges. But it places additional pressure on his legal defense by reinforcing findings that the financial statements at the heart of multiple cases were unreliable.

As Mr. Trump campaigns while navigating the criminal justice system, the courts continue to build a record that contrasts sharply with his public claims of business success and personal honesty.

With jury selection approaching in the Manhattan criminal trial, prosecutors now enter the courtroom armed with another guilty plea from inside Mr. Trump’s inner circle — and another reminder that the legal consequences of his business practices are still unfolding.