Weisselberg, regarded as one of Mr Trump’s most devoted business associates, has been with the former president for nearly 50 years. When he was arrested last year, he had left his job as chief financial officer, which he had held since 2005.
In this case, the Trump Organization is also a defendant, and its lawyers have entered a not guilty plea.
After agreeing to a plea deal first reported by The New York Times, Weisselberg must now testify against the company in a criminal trial later this year.
According to reports, he refused to cooperate with prosecutors in their larger investigation into Donald Trump and his business practices.
That means any testimony he gives at the trial, which is set to begin in late October, will be limited to this case and will not directly implicate the former president.
According to The New York Times, Weisselberg was under intense pressure from prosecutors to cooperate against Mr Trump, but he refused and accepted jail time.
Judge Juan Merchan said on Thursday that he will be sentenced at the conclusion of The Trump Organization trial. According to US media, he could be released from a likely five-month sentence after 100 days if time is credited for good behaviour.
That is far less than the many years in state prison he could have faced if he had been convicted at trial rather than pleading guilty.
Weisselberg’s guilty plea, which legal experts believe will strengthen the case against The Trump Organization, comes at a time when Mr. Trump is being investigated on multiple fronts.
He refused to answer questions last week as part of a separate New York state investigation into his family’s business practises. That investigation is a civil one, which means it will not result in criminal charges.
Mr Trump, who denies wrongdoing, had filed a lawsuit in an attempt to prevent the interview from taking place at the attorney general’s office. However, the questioning lasted approximately four hours, and Mr Trump, who invoked his Fifth Amendment rights, repeatedly said “same answer” throughout.
Separate investigations are also underway into the former president’s handling of classified documents, which prompted the FBI to search his Florida home, as well as his efforts to undermine the outcome of the 2020 election.
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