How Donald Trump Deterred His Sister Maryanne From A Real Estate Career

For most of her life, Maryanne Trump Barry had a good relationship with her brother, Donald Trump. Sadly, Barry was found dead in her apartment on November 13, 2023, at 86-years-old. She was a former judge for the U.S. Court of Appeals for the Third Circuit — a position appointed to her by then-president Bill Clinton in 1999. Following her death, Trump shared kind words about his sister. "A truly beautiful woman, tall and elegant, with a presence like no other," he wrote on Truth Social on November 14. "Her life was largely problem free, PERFECT, until I made it difficult for her when I decided to run for President," he added.

The siblings had different personalities  and different approaches to their careers. "She's quiet. She doesn't go to the balls," Robin Bernstein, a friend of the Trump family, told The Seattle Times in 2016. They overcame those differences and were relatively close in the past, but reports indicated that Barry and Trump grew apart in the years leading up to her death. "Maryanne loved her brother but basically gave up on him," a source told People on November 14.

Barry's foray into law was due in part to those differing personalities, as it made her shy away from the family business of real estate. "I knew better even as a child than to even attempt to compete with Donald," she told New York Magazine in 2002. "I wouldn't have been able to win." Real estate was her brother's domain, but Barry did dabble in selling properties. 

Donald Trump was glad that Maryanne Trump Barry decided to pursue a career in law instead of the family real estate business. "We're both lucky she didn't want to. We'd have been butting heads," he told New York Magazine in 2002. However, Barry tried to work for the family business when she was younger but said her talents were squandered on "women's work," such as decorating properties.

The former federal judge may not have pursued real estate as a career, but she turned a profit on several properties. In 2015, Barry sold a Palm Beach mansion for $8.9 million, per The Real Deal. The property, located next to her brother's Mar-a-Lago country club, was originally purchased by Barry in 2001 for $1.75 million. She tore down the existing home and built a new one. A few years later, Barry sold an estate in Palm Springs to Trump's sons for $18.5 million, per the Los Angeles Times. That eight-bedroom home was originally purchased in 2004 for $11.5 million.

Barry may have made some cash on her homes, but she lacked the passion for real estate that her brother had always exhibited. Trump spoke about his interest in an interview with The Washington Post in 1980. "In my case, by the way, my art is my real estate and my buildings, and if the deals work out well, that makes me happy," he told the Post. Ultimately, real estate was not why Trump and his sister grew apart.

Over the years, Donald Trump valued the advice of Maryanne Trump Barry. When he was searching to fill a vacancy in the Supreme Court in 2017, it was reported that the then-president had turned to his sister for guidance. Reportedly, Barry suggested Judge Thomas Hardiman, a colleague and friend of hers, for the position. "Maryanne is high on Hardiman," an advisor told Politico at the time.

In 2019, Barry's career came to a sudden halt thanks in part to her brother. She retired as a judge in the U.S. Court of Appeals for the Third Circuit amid controversy. A scandal broke that the Trump family had participated in tax fraud to increase their inheritance, and Barry was named among the conspirators. The former judge stepped down, saving herself from further legal scrutiny.

The relationship between Trump and Barry hit a rough patch the following year when audio tapes leaked of Barry disparaging her brother. "It's the phoniness of it all. It's the phoniness and this cruelty. Donald is cruel," Barry said in a conversation secretly recorded by her niece, Mary Trump, in 2018. In another conversation from the tapes, Barry claimed that Donald had other people take exams for him in college, and that was how he got accepted. "He had somebody take his entrance exams?" Mary asked. "SATs or whatever ... That's what I believe," Donald's sister responded.