Trump Organization Under Criminal Investigation by Manhattan DA

Origins of the Probe

The Manhattan District Attorney’s investigation into Donald Trump and the Trump Organization had its roots in the 2018 hush money payments case involving Michael Cohen. Under DA Cyrus Vance Jr., the inquiry gradually broadened to examine whether the Trump Organization had manipulated the valuations of its real estate holdings to obtain favorable loan terms from banks and reduce tax obligations. By early 2021, the investigation had expanded significantly, with prosecutors issuing subpoenas and interviewing witnesses across the company’s sprawling business operations.

Escalation to Criminal Investigation

In May 2021, the investigation took a dramatic turn when prosecutors convened a special grand jury, signaling that criminal charges could be forthcoming. The grand jury’s formation indicated that the district attorney’s office had moved beyond merely gathering evidence and was now actively considering indictments. Prosecutors were examining whether the Trump Organization had systematically inflated property values when seeking loans while deflating those same values to minimize tax bills.

The Tax Returns Fight

A critical component of the investigation was the battle to obtain Trump’s tax returns. The case went all the way to the Supreme Court twice, with Trump’s lawyers arguing that a sitting president was immune from criminal investigation. In February 2021, the Supreme Court cleared the way for Vance’s office to obtain eight years of Trump’s personal and corporate tax records from his accounting firm, Mazars USA. The records provided prosecutors with a detailed financial roadmap of Trump’s business empire.

Broader Implications

The criminal investigation represented one of the most serious legal threats Trump had ever faced. Unlike congressional inquiries or civil lawsuits, a criminal conviction could carry prison time. The probe also put intense pressure on Trump Organization executives, particularly CFO Allen Weisselberg, whom prosecutors would later pressure to cooperate against his longtime employer. Trump repeatedly denounced the investigation as a politically motivated “witch hunt,” a characterization he would apply to virtually every legal proceeding brought against him.