Prosecutors with the Manhattan district attorney’s office had been investigating Calamari, the chief operating officer of the Trump Organization, for off-books compensation that he received as a top executive, including a company-funded apartment and car, and whether he paid taxes on those benefits.
Informing Calamari that he will not be charged, at least for now, suggests a different tactic than prosecutors trying to “flip” him to gain his cooperation.
The decision not to pursue charges against Calamari at this time comes as prosecutors have sharpened their focus on the Trump Organization and how it valued certain assets, including office towers and golf courses, and whether it inflated those values to obtain loans or receive tax benefits while lowering those values for tax payment purposes, CNN has reported.
Cyrus Vance Jr., the Manhattan district attorney, is in the final weeks of his term after deciding not to run for re-election. While many expected Vance to decide whether or not to seek other charges against the Trump Organization or its executives before he left office, now it is less certain that he will.
The investigation has faced delays, including litigation that went to the Supreme Court, and a sealed legal dispute that is ongoing and relates to a subpoena for documents, people familiar with the matter say.
The Trump Organization and Chief Financial Officer Allen Weisselberg were indicted in July on charges they ran a 15-year tax fraud scheme. The company and Weisselberg have pleaded not guilty. Former President Donald Trump has called the investigation a politically motivated witch hunt.
The tax charges came years into the district attorney’s investigation into the company, which initially began scrutinizing a hush-money payment scheme. The investigation grew to focus on how the company valued many of its assets, including New York office towers and golf courses.
Prosecutors began focusing on Weisselberg to put pressure on him to cooperate with their investigation. He refused, and both Weisselberg and the Trump Organization were charged this summer.
The investigation’s focus has continued on valuations.
Calamari, like Weisselberg, has been with the Trump Organization for several decades and is fiercely loyal to Trump. It’s possible that prosecutors concluded Calamari would not agree to cooperate or that he did not have enough of value to give them to pressure him with criminal charges.
Weisselberg was charged with helping orchestrate the alleged tax fraud scheme. Calamari, by contrast, is viewed more like the head of security — even though his title is COO — and often has the responsibility to report to buildings and properties at all hours. His son, Matthew Calamari Jr., holds the title of director of security for the Trump Organization.
Compensation cases and property valuation cases turn on a number of factors, and many defense lawyers and former prosecutors say they can be difficult cases to make.
This story has been updated with additional details.