Trump’s Sister, The Judge: A Life Vastly Different, But Often Intertwined

Matt Katz | May 18, 2016 | Katz on Christie

When the oldest of the Trump children, Maryanne Trump Barry, graduated from law school as a stay-at-home mother and landed a job at the US Attorney’s Office in New Jersey in the 1970s, she was one of just two women in a 62-lawyer office.

“Scared?” Trump Barry recalled at a 2011 commencement address at Fairfield University. “Every day of my life.”

An admittedly scared Trump! Hard to imagine. The differences don’t end there.

Trump’s big sister is a private person who once described Donald as PT Barnum, according to the book “Trump Nation.” She has taken positions viewed as pro-choice (which subjected her to attack ads during the GOP primary this year). And in stark contrast to the apparent Republican nominee, she has repeatedly expressed pro-immigrant views. In 2006 she issued a revealing opinion on a deportation case, saying that Americans should be ashamed if they don’t heed the welcome message under the Statue of Liberty.

“Neither of my parents had English as a first language,” she once recalled. “My father’s father died when he was a teenager, and dad went to work to support his mother and two siblings as a carpenter and as a builder’s mule, hauling carts of lumber to construction sites when it was too icey for the mules to climb the hills.” 

That Trump immigrant story is not one of her brother’s talking points.

And yet despite any ideological differences, the siblings’ professional lives have long been intertwined, from her appointment to the federal bench in 1983 to a mysterious drug case involving Donald Trump’s friend several years later and right on to the Bridgegate scandal, which could wind up in her lap. Barry Trump, a Manhattan resident, became a federal court judge in Newark in 1983 and was elevated to the Third Circuit Court of Appeals in 1999. And she could be chosen to serve on a panel that will decide on June 6 whether to make the names of unindicted Bridgegate co-conspirators public.  

Of course, if chosen, she would likely recuse herself from the case. After all, not only does she know Gov. Chris Christie — whose associates, past or present, are surely on that list of co-conspirators — but she introduced him to her brother. After Christie became US Attorney of New Jersey in 2002, he made a courtesy call to Trump Barry’s chambers. She told Christie that her brother wanted to meet him. Shortly thereafter, the men had dinner and became friends.  

The siblings are said to be close. She was a bridesmaid at his first wedding, and he sought her advice after he was lambasted for referring to Fox News anchor Megyn Kelly’s menstrual cycle.

After Trump Barry had foot surgery, Trump visited her every day in the hospital. In 1993, when Donald was broke, Trump Barry and other siblings lent him millions of dollars to keep his real estate and casino empire afloat (although Trump later denied this). And this year, in speeches after winning primaries, he thanked “Maryanne, a really great sister.” 

Lawyers who know say that despite getting an icy reception from the Bar Association when she was first nominated to a judgeship in 1983, she is now widely respected. She is known for being well-prepared, and will not hesitate to dress down attorneys or judges

David Lat, a lawyer and founder of, which covers the legal profession, says that Trump Barry drinks single malt scotch and drives a red Jaguar. She also might be the richest member of the federal bench.

But that’s not why Lat long ago dubbed her a “judicial diva.” It’s because of what she herself reportedly said after she was not named to a list of the hottest judges in the judiciary.

“One of Judge Barry’s clerks asked her, ‘Judge, were you upset not to make the list of super hotties when colleague and friend Judge [Marjorie] Rendell did?'” Lat recalled. “Judge Barry responded: ‘Hotness fades. Divahood is forever.'”

And yet this diva is known to slum it for lunch in the cafeteria at the federal courthouse in Newark. “She waited in line just like everyone else,” said Lat, who used to work in that same building. “It was just kind of funny to see her because she dresses very well, she has this elaborate, almost architectural blonde hair, a little bit like her brother.” 

Also like her brother: Trump Barry is known for her candor. She once chastised women who describe flirtations from male colleagues as sexual harassment.

“Every sexy joke of long ago, every flirtation, is being recalled by some women and revised and re-evaluated as sexual harassment,” she said in 1992. “Frivolous accusations reduce, if not eliminate, not only communication between men and women but any kind of playfulness and banter…Where has the laughter gone?” 

The comments drew this anonymous criticism from a female lawyer, who told The New York Times that not all lawyers have the benefits of being “tall, blonde, beautiful, rich and had Roy Cohn as a sponsor.”

Cohn, a Republican lawyer and aide to communist-hunting Senator Joe McCarthy, was her brother’s mentor. Considered a political henchman, Cohn is believed to have taught Trump to say anything to win. Trump Barry did not respond to three calls to her court for this story, but she previously told an interviewer that there was “no question” that her brother helped her get her judgeship. Cohn was plugged into the Reagan White House at the time, and she reportedly called to specifically thank him after the appointment.

Yet as former New Jersey Gov. Tom Kean remembers it, political connections played no part in her selection. “I didn’t know it was Trump’s sister!” Kean told WNYC.

As the state’s top Republican, Kean got a call from a top Reagan aide. The White House was looking for a female Republican to appoint to federal court. So Kean created an informal screening committee.

“And they kept recommending the same person without talking to each other, and it was a woman who worked for the US Attorney’s Office called Maryanne Barry,” he said. No one told Kean her middle name — Trump.

Her political connections though would soon be apparent. As she sat on the bench in New Jersey, her husband, John Barry, worked as an attorney for Trump and his New Jersey casinos. In fact his law firm in those years — Kimmelman, Wolff and Samson — has been tied into the upper echelons of New Jersey power right through the Christie Administration. Its namesake, Irving Kimmelman, was for a time the state’s Attorney General and in a position to oversee the regulation of Donald Trump’s casinos. Later, the head of the state’s Division of Gaming Enforcement, which regulates the gambling industry, went to work at the firm as a partner. 

Another partner, David Samson, would one day become Christie’s closest confidante before becoming embroiled in scandal. The firm recently changed its name after allegations surfaced of Samson’s impropriety. 

Trump biographer Wayne Barrett believes John Barry’s legal work for his brother-in-law is important when considering his wife’s tenure on the court. “Maryanne Trump — who is living on a federal judge’s salary, which is not much to live on — literally her wealth depended on her husband’s representation of the Trump casino empire,” he said. John Barry died in 2000, shortly after the death of Trump Barry’s father. Barrett said the Trump children didn’t inherit the bulk of the family wealth until the patriarch’s death.

There is no evidence that Trump Barry ruled on matters involving her brother, but Barrett contends that the nexus of personal, business and political relationships calls into question another episode in Trump Barry’s career.

According to court documents, state records and published reports from the the 1980s and 90s, Donald Trump’s friend and business associate, Joey Weichselbaum, was arrested for trafficking drugs. Weichselbaum lived in one of Trump’s buildings, paying rent partially in cash and partially through services provided by Weichselbaum’s helicopter company. The company ferried high rollers to Trump casinos.

After Weichselbaum was convicted, Trump wrote a letter to the court seeking a lenient sentence — a fact which he later couldn’t recall, according to a 1992 investigative report from the Casino Control Commission. The letter was first revealed in Barrett’s book, “Trump: The Deals and the Downfall,” and is believed to be the only time Trump wrote such a letter.

But there was something else unusual about this incident. After the conviction but before the sentencing, the matter was moved from an Ohio court to none other than Trump Barry’s courtroom in Newark. 

“In my career I don’t recall having any cases other than that one which would have been transferred from one district to another,” said IRS agent Leo Rolfes.

Both he and the case’s prosecutor, Anne Marie Tracey, told WNYC that this change in venues was unprecedented and unexplained. “I’ve never had this happen before,” said Tracey, who has 40 years of experience as a lawyer, prosecutor and judge. “It is an anomaly.”

A spokeswoman for the presidential candidate did not return a request for comment on this matter.

Trump Barry ultimately turned the case over to a colleague, who sentenced Weichselbaum to three years in prison. His attorney at the time, Michael Critchley, says nothing inappropriate transpired.

Another incident stands out, back when Trump Barry was in the US Attorney’s Office. A Queens immigration lawyer represented 200 illegal immigrants who were subject to horrendous work conditions while demolishing a Manhattan building to make way for Trump Tower. The lawyer, John Szabo, took his concerns to the US Attorney’s Office, where he was given a stern warning. He remembered it this way in the 1991 documentary, “Trump: What’s the Deal?”

“The Assistant US Attorney said, ‘Don’t say the name Trump in here,'” Szabo alleged. “If you want to talk about Trump, let’s go outside and talk.” 

In the end, a subcontractor, not the Trump Organization itself, was convicted of importing and exploiting the Polish workers.

These controversies did not surface in 1999, when President Clinton elevated Trump Barry to federal appellate court judge for the Third Circuit. Her name was recommended by Bob Torricelli, the state’s Democratic senator at the time. He described her as a respected and excellent jurist. 

“She was a Republican, but I thought in her cases had been fair, independent of the government, with a reputation of running a fair courtroom,” he told WNYC.

The former senator says he was never even lobbied for the promotion by her powerful brother. “He actually never called me about it,” Torricelli said. “Even though we knew each other well for years. We never spoke about it.” 

But after the nomination, Trump did call the senator. Just to say thanks.