The Trump Organization and its longtime chief financial officer on Thursday pleaded not guilty to tax evasion charges in a New York court, in a widening criminal case against Donald Trump’s business that could complicate his political future.

The charges focus on whether Allen Weisselberg and other company executives received benefits and perks such as rent-free apartments, private school fees and cars, without reporting them properly on their tax returns.

"This was a 15-year long tax fraud scheme involving off-the-books payments,” said Assistant District Attorney Carey Dunne, adding that Mr Weisselberg is accused of not paying taxes on $1.7 million (£1.3m) in income.

"It was orchestrated by the most senior executives who were financially benefiting themselves and the company, by getting secret pay raises at the expense of state and federal taxpayers," he said, accusing Mr Weisselberg of directing company records to be deleted.

Mr Weisselberg, who was escorted into the courtroom wearing handcuffs and a facemask, faces up to 15 years in prison on charges of grand larceny in the second degree, while the Trump Organization was charged with a scheme to defraud in the first degree.

Dismissing accusations from the company that the charges were politically motivated, Mr Dunne told the judge that "politics has no role in the jury chamber and I can assure you it had no role here.”

Court filings, public records and subpoenaed documents show that Ms Weisselberg, 73, and his son Barry have received benefits and gifts potentially worth hundreds of thousands of dollars.

New York prosecutors have in recent months exerted pressure on Mr Weisselberg, who has worked for the Trump family business for nearly half a century, to turn on Mr Trump and cooperate with their broader investigation into the former president’s business dealings.

Cyrus Vance, Manhattan district attorney, arrives outside the Manhattan district attorney office in New York

Credit: Bloomberg

Mr Weisselberg, often described as Mr Trump’s most loyal lieutenant and gatekeeper of company secrets, has so far refused to turn supergrass on his boss, however, he could still strike a deal after his arraignment.

Mr Trump is not currently facing any individual charges.

Former prosecutors have suggested, however, that Thursday’s indictment could be the first in a series of charges, particularly if Manhattan District Attorney Cyrus Vance’s office is able to gain the cooperation of Mr Weisselberg in future.

The three-year investigation appeared to speed up once Mr Vance’s office won a lengthy battle in February to obtain the former president’s personal and corporate tax returns and underlying financial documents.

Mr Vance is probing whether the Trump Organization regularly overvalued or undervalued its assets, particularly several properties in New York state, to either get bank loans or reduce their taxes.

Allen Weisselberg has worked for the Trump family for nearly five decades

Credit: The Trump Organization

In a statement on Thursday, the Trump Organization said prosecutors were using Mr Weisselberg as "a pawn in a scorched earth attempt to harm the former president."

"This is not justice; this is politics," the company said in a statement ahead of the court hearing.

An indictment of the Trump Organization could complicate Mr Trump’s political future as the Republican contemplates running again for president in 2024, as well as undermine the company’s relationships with banks and business partners.

A private family-run business, the Trump Organization operates hotels, golf courses, and resorts around the world. Mr Trump handed over the reins to its three executive board members – his sons Eric and Donald Jnr and Mr Weisselberg – before entering the White House in 2017.

A bookkeeper by training who grew up in Brooklyn, New York, Mr Weisselberg rose steadily within the Trump Organization to become perhaps the former president’s most trusted business adviser.

The two families became intertwined over the decades, with Mr Weisselberg’s two sons taking up roles within the Trump Organization.