Weisselberg,75, pleaded guilty to all 15 counts - including conspiracy, criminal tax fraud, grand larceny and falsifying business records - conceding he skirted taxes on nearly $2 million in income, including fringe benefits like rent, luxury cars and private school tuition for his grandchildren.
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The plea implicates former President Trump's namesake family business, which was charged in the same indictment by the Manhattan District Attorney's office.
Weisselberg repeatedly answered "yes your honor" as Judge Juan Merchan asked a series of questions about the scheme to evade taxes, admitting he falsely underreported compensation, including a luxury apartment on Riverside Drive in Manhattan, multiple Mercedes Benz cars, cash, private school tuition for his grandchildren and additional homes.
As part of his plea deal, Weisselberg agreed to serve five months in prison followed by five years of supervised release. He also agreed to testify against the Trump Organization when the company goes on trial in connection with the alleged compensation scheme beginning in October. If he does not testify truthfully, the deal is off, exposing Weisselberg to additional prison time of between five and 15 years.
*The defendant must agree to testify truthfully at the trial of the Trump Organization," assistant district attorney Joshua Steinglass said.
Weisselberg must also pay back taxes and penalties totaling $1.94 million.
"This plea agreement directly implicates the Trump Organization in a wide range of criminal activity and requires Weisselberg to provide invaluable testimony in the upcoming trial against the corporation," said Manhattan D.A. Alvin Bragg. "Furthermore, thanks to the incredibly hard work and dedication of the team prosecuting this case, Weisselberg will spend time behind bars. We look forward to proving our case in court against the Trump Organization."
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A corporate tax fraud case was not what prosecutors were after. When they first filed charges against Weisselberg last summer, prosecutors hoped Weisselberg would turn on Trump, sources have told ABC News.
The plea agreement contains no requirement for Weisselberg to cooperate in the criminal case against Trump himself, which centers on whether the former president knowingly misled tax authorities, lenders and insurance brokers by providing inaccurate financial statements about the value of his real estate portfolio.
Trump asserted his Fifth Amendment right against self-incrimination during a deposition last week as part of a parallel civil investigation by the New York Attorney General's office.
The criminal investigation, which began under former DA Cy Vance, appeared to stall earlier this year when the two senior prosecutors leading it resigned amid frustration the new district attorney, Alvin Bragg, seemed to not immediately seek an indictment against Trump, sources told ABC News.
Bragg's office has said the investigation remains ongoing.