By using a long-running conflict between two feuding family fiefdoms, New York prosecutors appear to have found an opening they can use to tear open the highly insulated Trump Organization and get beyond its mob-like code of silence.
Allen and Barry Weisselberg, the company’s long-time chief financial officer and his son, are pitted against Matthew Calamari Sr. and Jr., the company’s chief operational officer and his son.
Former President Donald Trump has always appeared to be the subject of this three-year criminal investigation. To catch him, investigators may need to turn over Allen Weisselberg, his right-hand man in finance.
But in order to get him, they’ll need to use his subordinate, accountant Jeffrey S. McConney. And it appears that they’ve discovered a way to put pressure on him: “Matty” Calamari Jr.
Prosecutors are attempting to use the Trump Organization’s young head of corporate security, Matty, to collect damaging information about the company’s controller, McConney, according to two people familiar with the situation.
According to one of those individuals, Matty’s sole connection to McConney is that the accountant handled his personal tax returns years ago, and authorities are investigating whether those returns correctly represented data about his domicile, business apartment, and vehicle.
As a result, “Matty Jr.” was summoned to testify before the grand jury on September 2. According to this source, McConney was also brought in a second time later that day.
According to two additional people familiar with the situation, Donald Trump has reminded business colleagues and other members of his inner circle about the necessity for Trump Organization personnel to “stick together” and stay strong in several meetings and phone conversations since the spring.
The message made by the twice-impeached former president was simple: his subordinates and confidants should not enable New York investigators to manipulate or play employees off one another during the criminal investigation into the Trump family enterprise.
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Those requests for continuing devotion extend to the older Weisselberg, despite the fact that his name has been removed from Trump company records since his indictment last summer.
Prosecutors, on the other hand, are banking on the ex-appeals president’s for unity falling on deaf ears.
The Weisselbergs and Calamaris have a long history of animosity, which stems from their steadfast support for Trump. Two long-time friends recounted a Shakespearean battle between opposing dynasties, with dukes fighting for the king’s favor.
“They hate each other. It’s a war,” said Jennifer Weisselberg, who is going through a bitter divorce with Barry Weisselberg and has become a witness for New York prosecutors.
If the current effort succeeds, McConney might be a valuable witness. McConney has worked directly for Allen Weisselberg for over 30 years, cutting checks, executing transactions, and putting deals in place. In theory, the trustworthy corporate money man should be aware of any potential financial wrongdoing.
Until recently, it appeared unlikely that McConney would be used. He has a reputation as a devoted business footsoldier who despises the political left and keeps his lips quiet. When the New York Attorney General’s Office interviewed him for its earlier investigation of the Trump Foundation, McConney protected higher-ups by assuming the blame and attributing possibly illegal activity to simple accounting errors, as The Daily Beast exposed in July. And it’s unclear if McConney was of any assistance to the prosecution when he testified before the grand jury in this case last spring.
However, any incriminating information from Matty might shift the equation.
This was not unnoticed. This summer, it became more common knowledge—as well as a source of concern and annoyance—in the upper echelons of Trump’s business and personal circles that prosecutors have been attempting to use multiple Trump-linked families against each other, according to people with knowledge of the situation.
Each of these families has had numerous members hired by Trump, and each family contains dads who have sworn professional, emotional, or even political loyalty to The Donald and his family.
The Manhattan district attorney’s office and the New York state attorney’s office, which are working on this case together, declined to comment. The Trump Organization and the former president’s spokespeople did not reply to requests for comment on this story.
McConney and his attorney, Patricia Pileggi, did not respond to requests for comment for this article. Allen Weisselberg and his attorneys, Brian C. Skarlatos and Mary E. Mulligan, didn’t either. The Calamaris and their attorney, Nicholas A. Gravante Jr., did not respond to requests for comment.
The Trump Organization is riddled with nepotism, which is a feature, not a flaw. The general public is well aware of how Trump placed his daughter and two sons in positions of power both before and during his presidency. However, it is less well known that Allen Weisselberg’s son, Barry, has overseen the company’s Wollman ice rink in Central Park for many years—or that COO Matthew Calamari’s son, Matt Jr., is the head of corporate security.
Allen Weisselberg is a relic from Donald Trump’s father, Fred. Allen began working as an accountant in 1973, just a few years after graduating from college, at his father’s real estate firm in Brooklyn. In 1986, he switched to the son’s developing business and became Donald Trump’s corporate controller.
According to colleagues, Weisselberg stayed through painful bankruptcies and failed business ventures, with McConney working under his supervision as a lower-ranking accountant. McConney took over as corporate controller when Weisselberg was promoted to chief financial officer of the Trump Organization.
Weisselberg became the don’s right-hand man because to his financial expertise and personal allegiance to the Trump family. While Trump conceived of deals, Weisselberg secured finance, and McConney carried out his boss’s strategy. According to two individuals, Weisselberg always had the ultimate word when it came to arranging employee remuneration. According to one person acquainted with the yearly routine, it was he who would meet in a separate room with Trump each year and determine what they deemed the right monetary valuations for their large real estate portfolio—and what they should pay in taxes appropriately.
It’s no wonder, therefore, that when Trump became president and was obliged to step aside from the day-to-day operations of his corporate empire, he put Weisselberg in command of the trust that owned and managed the organization and the then-assets, president’s alongside Eric Trump and Donald Trump Jr.
Weisselberg threw his own family into the mix along the way. His son Barry took over as manager of Trump’s Central Park ice rink. His other son, Jack, did not join the Trump Organization directly but remained on the outskirts as a director at Ladder Capital Corp., which has made multiple loans to the firm.
In the meantime, Matthew Calamari Sr. followed a similar but somewhat different path into Trump’s inner circle. He began as Trump’s hired muscle. Barbara A. Res, an engineer who oversaw building projects for the firm in the 1980s, told The Daily Beast that she remembers Calamari getting his foot in the door.
Trump first spotted him when attending the 1981 U.S. Open semifinal tennis event in New York City, where Calamari was the security guard who pounced on two young guys and killed them quickly. Trump was so delighted that he phoned Res, who was directing the building of Trump Tower, on Monday morning and informed her, “I got this man… we’ll put him in head of security!”
She advised him against doing so and suggested he employ a firm instead. Trump, on the other hand, seems unconvinced. Calamari, who had just graduated from college and had played football, was charged with defending the structure while it was being built.
Calamari became the chief of security at Trump Tower once it was completed. He was later promoted as Trump’s personal bodyguard. Several sources who have flown in and out of Trump’s orbit over the years told The Daily Beast that the real estate mogul hired him as a bodyguard and occasional chauffeur, primarily because he looked and sounded like a typical New York labor union tough guy—or, at the very least, the caricature of a tough guy in Trump’s mind.
According to reports, over Calamari’s many years of dedicating his life to serve the House of Trump, the famed, tabloid-dominating billionaire loved having Calamari physically near him as a blunt instrument of sorts. According to the sources, Trump thought Calamari contributed to his intimidating and brutal demeanor.
One person with direct knowledge of the situation said Trump had “fetishized” Calamari’s appearance and persona and that they had been present on multiple occasions when Trump would point to or mention Calamari and then joke to people around him that Calamari “will kick your ass, watch out,” or that he could “kill you” very quickly.
By 1992, Calamari was vice president of corporate security, in charge of not only safeguarding Trump’s property, but also leading the internal investigation that led to the arrest of the man who broke into the apartment of Trump’s lover, Marla Maples—who would eventually become his wife.
Calamari “got [the guy] to willingly consent to a search of his Manhattan office,” as Newsday put it at the time. When one employee claimed to have discovered proof of “financial improprieties” and brought his wife and child to the office to pick up paperwork, Calamari and his security team stopped them—and allegedly detained them, according to a lawsuit that never went anywhere.
Calamari had risen to the position of chief operational officer, managing improvement initiatives, by the time he made a brief appearance on The Apprentice in 2004 (during which he froze and was unable to articulate entire ideas).
Calamari, like Weisselberg, welcomed his kid into the fold. According to Matty’s online CV, he worked security for the firm while in college, only to follow in his father’s footsteps and climb to the position of head of corporate security in 2017.
According to long-time colleagues, although the Weisselbergs and Calamaris fight for The Donald’s favor, they also believe that each is entitled to the benefits that the other has received.
For example, in 2004, Trump gave Barry and Jennifer Weisselberg a luxurious condominium at 100 Central Park South, one of Manhattan’s most desired addresses because to its proximity to the city’s largest stretch of green. According to a person with knowledge of the encounter, years later, Matthew Calamari Sr. asked Trump why his son shouldn’t get the same treatment. According to two acquaintances and a neighbor, Calamari Jr. ultimately acquired a corporate apartment in the same building.
According to two associates and two neighbors, whereas Allen Weisselberg received a corporate apartment facing the Hudson River and the New Jersey skyline, Matthew Calamari Sr. received a high-end corporate unit at the Trump Park Avenue building four blocks away from Trump Tower.
However, this tit-for-tat has exposed the Calamaris to a possible prosecution.
The indictment issued on June 30 against Allen Weisselberg, the sole person accused thus far, says that he got significant perks in the form of residences and automobiles that were not taxed in the same way that additional pay would be. The charge document cites his Riverside Boulevard condominium, his son’s old residence facing Central Park, and two Mercedes automobiles.
Meanwhile, the Calamaris are likely to defend their freebies by claiming that their employment demand being a short walk away from the business offices. After all, they both deal with security concerns ranging from midnight crises to random calls from police and fire departments—especially after the firm founder became one of the world’s most despised individuals.
People who submit confidential testimony before a grand jury in New York are granted immunity for what they reveal, so McConney and the younger Calamari may be safe. Prosecutors might still file perjury charges against either of them if they lie.
However, the elder Calamari and younger Weisselberg are widely regarded as being on the short list of Trump Organization officials who may be prosecuted next for receiving untaxed benefits—and further law enforcement action looks to be on the way.
During a court hearing on Monday, Allen Weisselberg’s counsel claimed that investigators uncovered evidence in the basement of an unknown co-conspirator. Skarlatos, the attorney, went on to say that he had “strong reason to believe there could be other indictments coming.”