Loyal Trump Aide Gets His Mug Shot: Meet CFO Allen Weisselberg

(Bloomberg) -- Allen Weisselberg has spent almost his entire adult life working for the Trump family. That lifetime of work may now send him to prison.

The Trump Organization's chief financial officer is expected to turn himself into authorities on Thursday morning in New York, accused of unpaid taxes on benefits he received from his employer, including use of a company car and a corporate apartment, according to people familiar with the matter. His lawyer didn't respond to requests for comment.

Weisselberg's importance to the former president far eclipses his title -- the 73-year-old has served the family for more than 40 years and is the only person not named Trump whom the ex-president trusts with his money. He's negotiated Trump's loans, is a co-signer on his accounts, helps arrange his taxes, and, with Trump's sons Don Jr. and Eric, oversaw the trust that held all of Trump's assets while he was in office.

He “knows of every dime that leaves the building,” Corey Lewandowski and David Bossie wrote last year in a book about their time running Trump's presidential campaign.

Weisselberg joined the organization in the 1970s, as an accountant for Trump's father, Fred. Donald Trump and Weisselberg are contemporaries -- only a year apart in age -- but their relationship evolved over the years as Weisselberg went from helping a young Donald navigate his father's business to standing by his side as Trump ascended to the top role.

For years, the squat, bespectacled and mustachioed Weisselberg commuted from a simple Long Island home in Wantagh to his office in Trump Tower, a far cry from the boss's splashy lifestyle. That began to change in the early 2000s, with the Weisselbergs becoming more closely knit with the Trumps in ways unusual for an owner and his CFO. Weisselberg and his wife moved into a luxury Trump apartment in Manhattan, though he retains the Brooklyn accent from his Brownsville youth.

Weisselberg's two sons pursued careers that were linked to Trump. Jack Weisselberg works at Ladder Capital, a commercial real estate lender that has done business with the Trump Organization. Barry Weisselberg earned about $200,000 a year managing Wollman Rink in Central Park, a New York City property that the Trump Organization operated until earlier this year.

According to sealed records reviewed by Bloomberg News from Barry Weisselberg's divorce, the Trump Organization provided the couple with a rent-free apartment overlooking Central Park for more than a decade. The Manhattan District Attorney has been investigating a range of similar perks granted to determine if the Weisselbergs paid the appropriate taxes associated with the benefits.

Weisselberg isn't the only Trump aide to face charges -- former Trump lawyer Michael Cohen was sentenced in 2018 to three years in federal prison for tax evasion and other crimes, after being with the company for more than a decade.