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Trump thought New York City was his playground. Now, it's his nightmare.

Judge Engoron just handed Trump 355 million reminders that he is not, in fact, above our great city's laws.

New Yorkers are no stranger to Donald Trump’s legal problems.

Starting decades ago, knowledgeable residents of the Big Apple witnessed the Trump family cheat and rig the system for their own benefit. So what’s truly interesting about Friday's New York civil fraud decision is that Trump and his co-defendants are finally being held financially accountable — to the tune of over $350 million. This massive judgment highlights the extent of Trump and the Trump Organization’s white-collar malfeasance.

This massive judgment highlights the extent of Trump and the Trump Organization’s white-collar malfeasance.

Trump’s actions have consequences. And New York’s hardworking residents deserve to know that the rich and greedy don’t get to play by a different set of rules. As Kevin Wallace, a lawyer in New York Attorney General Letitia James’ office, said during closing arguments: Trump’s misconduct “prices out honest borrowers and can lead to more catastrophic results.”

Fortunately, an entirely new generation of New York public servants, not steeped in the traditions of “go along, get along,” have emerged to fight back. Their actions this week confirm that a long history of corruption is finally being overcome.

Judge Arthur Engoron, a classically blunt New Yorker, has consistently shown he is not overawed by the powerful man whose fate he holds in his hands.

And James, who like me started her political career as an insurgent City Council member, stood her ground against Trump in a way her predecessors never managed. But it didn’t always work this way.

In 1973, a federal investigation probed the racially discriminatory practices of Donald Trump and his father, Fred. The feds took exception to the Trump family’s habit of steering Black and Latino applicants away from their buildings where white people lived. Trump ultimately got a slap on the wrist, never acknowledged guilt and kept on discriminating.

That was just the beginning. The lesson Trump learned early on was: Bending the rules does pay. It’s a philosophy that has framed a lifetime of business dealings and which, at last, may be catching up with him. Cut corners whenever you can. Play fast and loose with the rules and worry about the consequences later.

On this journey, he brought along as his consigliere Roy Cohn, who got his start advising the eventually discredited Sen. Joe McCarthy. If you think undermining democracy is something new for Trump, look no further than the fact that he gainfully employed one of the prime architects of the McCarthy era.

Trump realized early on that he could get away with almost anything, so long as he was ready to retain enough pricey lawyers and donate to all the right political leaders.

Trump realized early on that he could get away with almost anything, so long as he was ready to retain enough pricey lawyers and donate to all the right political leaders.

And party registration had nothing to do with it: He and his minions happily supported Democrats and Republicans, depending on who would help them the most.

When it proved relatively painless to beat the housing discrimination rap in the 1970s, Trump decided to branch out. He allegedly cheated employees out of wages and tips and stiffed contractors. He has called mobsters “very nice people.” He allegedly found colorful and creative ways to evade taxation. At one point, his father purchased millions of dollars of Atlantic City casino chips he never intended to use, gifting them to his son to help the young developer make a bond payment, according to an investigation by The New York Times.

Donald Trump flying on his helicopter above New York City in 1987.
Donald Trump flying on his helicopter above New York City in 1987.Joe McNally / Getty Images file

What’s so striking is how we New Yorkers became accustomed to the cycle of allegation, investigation and then Houdini-like escape. Whenever the authorities closed in on yet another brazen Trump violation of the law, they ended up pulling their punch.

Maybe it was his New York connections or donations. Maybe it was his media profile or his propensity to countersue at all times. Or maybe it was simply that he created fear and doubt in the minds of those who were supposed to uphold an equal standard of justice.

In 1989, with literally no evidence to guide him, Trump took out full-page ads in New York City newspapers calling for the death penalty for five young Black men who were falsely accused of raping a white woman. This sickeningly brilliant propaganda act helped ensure that innocent New Yorkers would spend over a decade in prison. Even when they were later exonerated, Trump continued to blame them.

And so, the pattern became clear to so many of us: Trump believed that the laws of New York simply didn’t apply to him. He has treated our city like his personal playground. It is no surprise that he would later boast, as a presidential candidate, that he could shoot someone on Fifth Avenue and get away with it.

And for far too long, the authorities never proved him wrong.

And so, throughout the 1990s and into the current century, the pattern continued. Trump exaggerated his assets. James’ investigation concluded that he had cheated his business partners. He walked away from contractual obligations. He created an entire university based on fraudulently preying on low-income students seeking a better life. And nothing happened to him that would actually change his behavior.

Until now.

As New York’s mayor, I wasn’t cowed by his power or mystique. And now it seems his spell has finally worn off. "Their complete lack of contrition and remorse borders on the pathological," Judge Engoron wrote, before giving Trump 355 million reminders that he is not, in fact, above the law.