Weisselberg, 75, was sentenced to five months on Rikers Island, New York City's notorious jail complex, followed by five years' probation, after he pleaded guilty in August to orchestrating a 15-year tax scheme while working at the Trump Organization as chief financial officer.
As part of a plea deal, Weisselberg testified over three days in November against the Trump Organization at its criminal trial, which resulted in a conviction against the company for paying the personal expenses of some executives without reporting them as income, and for compensating them as independent contractors instead of full-time employees.
Weisselberg walked a fine line during his testimony in the Trump Organization trial. He conceded he evaded $1.7 million in taxes by taking part of his compensation in off-the-books luxuries like rent, car leases and private school tuition. He also said the scheme benefitted two entities of the Trump Organization -- Trump Corporation and Trump Payroll Corporation -- by causing them to have a lower payroll tax burden. However, he said nothing to implicate Trump himself in the scheme.
"Each month makes a big difference when you're 75 years old, because each week you're incarcerated represents a larger percentage of his life," Gravante said.The judge declined, saying an even stiffer sentence would be appropriate for conduct"driven by greed." Weisselberg, while no longer the Trump Organization's chief financial officer, remained employed with Trump's family real estate firm and expected to make more than $1 million last year in salary and bonuses, according to his testimony at trial.
Weisselberg testified at the trial of the Trump Organization that he reduced his reported salary by the total amount of personal expenses paid and that the company benefitted by paying less in payroll taxes. He also testified his primary motive was greed.