Once Trump’s bodyguard, Calamari is the Trump Org’s Chief Operating Officer. The COO is like a Chief of Staff and is second in rank to the CEO (Trump himself). There are seven different types of COO’s (heir, mentor, partner, MVP, opposite, change agent and executor). Calamari—who told Trump on video that he would kill for him—is obviously the executor type. That means his job has been to make sure that senior management’s orders are carried out efficiently and effectively. In a criminal organization, the COO would be responsible for overseeing the crooks and for making sure the crimes are carried out.
Michael Cohen named Matthew Calamari Sr as one of a handful of people who could confirm that the Trump Org frequently and fraudulently mis-valued real estate assets to banks, insurance companies and tax authorities. Calamari is currently being investigated by Cy Vance, the Manhattan District Attorney, as part of the broad investigation into whether the Trump Org is a criminal enterprise. (His son Matt Calamari Jr, Trump Org’s director of corporate security, is also under investigation). Both Calamari Sr and Jr drive luxury cars, live in luxury Trump apartments and have perks that are under investigation for alleged tax evasion.
The Chief Financial Officer, Alan Weisselberg, has gotten much of the attention so far, since he controls the money and has been serving Trump longest. But Calamari’s job puts him at the center of the investigation for several reasons.
- First, according to the CFO’s daughter in law, much alleged crime took place in payroll transactions that enabled tax evasion. The COO’s job includes overseeing both staff and efficient use of funds, so, in theory, he should know about any pattern of illegal payments (especially if both he and his son received them).
- Second, the COO is normally responsible for coordinating with both the CFO and the CEO, managing operations, ensuring that key initiatives are executed, and for putting corporate policies, procedures and practices in writing. If Calamari didn’t write anything down, that could be seen as a red flag that the organization is criminal.
- Third, the COO’s job often includes responding to general outside inquiries. While the CFO is responsible for delivering specific financial reports to regulators and the lawyers handle specific legal requests, the COO would normally oversee and coordinate the organization’s overall response to officials. Since the prosecutors and ultimately the judge will assess how well the Trump Org has cooperated with New York in being transparent, in demonstrating good corporate citizenship and for running a tight ship that investigates and reports corruption, the extent that the COO either participated in corruption and coverups, avoided due diligence, willfully ignored misconduct or refused to cooperate proactively with regulators, will be a key factor in determining how to punish the Trump Org. In other words, unless Calamari can explain what was going on and why he didn’t say anything, New York has every right to shut down and liquidate the Trump Org.
Investigators also need to understand Weisselberg’s true role. Some reports claim that Weisselberg is actually the unofficial COO, which if true would increase his legal jeopardy. As CFO, Weisselberg is already on the hook for the documents he signed, including many reports required by NY tax authorities. If Weisselberg claims that he was simply following corporate orders, then Calamari has to explain what orders he got from Trump and what he told Weisselberg to do. If Calamari denies telling Weisselberg to sign fraudulent documents, then Weisselberg has to explain what orders he received from Trump himself. If Weisselberg can’t blame anyone else, then prosecutors can paint Weisselberg as the mastermind and throw the book at him. And if the violations are found to have continued for many years, then the entire chain of events or the entire series of continuing illegal actions can be punished, not limited by the statute of limitations, which for Weisselberg could add up to a very long time indeed.