The Shady Side Of Maryanne Trump Barry, The Late Sister Of Donald

Donald Trump's older sister, Maryanne Trump Barry, died in November 2023 at age 86. The siblings had a tumultuous relationship over the years. In 2002, Donald was raving about Maryanne in a 2008 interview with New York Magazine. "She ultimately became a federal judge, one notch below the Supreme Court!" he boasted. However, things turned sour after Maryanne's shady side was exposed via secretly recorded tapes that allegedly revealed the untold truth about Donald Trump.

Donald took his time to acknowledge his sister's death, waiting until the day after her passing. He sandwiched his thoughts between an attack on New York Attorney General Letitia James and a post promoting his latest book. When he did get around to Maryanne, Donald posted a gushing eulogy on Truth Social to a "truly beautiful woman, tall and elegant, with a presence like no other." Although, he couldn't help inserting himself into the tribute. "Her life was largely problem free, PERFECT, until I made it difficult for her when I decided to run for President," Trump wrote.

There was no mention of the far-from-flattering things Donald's sister said about him and his family in the leaked tapes, which, by anyone's standards, were contentious, controversial, embarrassing, and biting. The 15 hours of recordings were secretly made by Donald and Maryanne's niece, Mary Trump, during conversations with her aunt. After The Washington Post obtained the tapes in August 2020, it's safe to say Maryanne's shady side and true feelings towards her brother were laid bare.

Maryanne Trump Barry backstabbed Donald big time

There was no hiding Maryanne Trump Barry's shady side after The Washington Post obtained secret recordings of conversations between Maryanne and her niece, Mary Trump. In the tapes, Maryanne lets rip regarding her thoughts about Donald Trump, who was president at the time. She accused him of being a phony who was only interested in pandering to core supporters and MAGA fanatics.

"He has no principles. None. None. And his base, I mean my God, if you were a religious person, you want to help people. Not do this," she told Mary regarding Donald's treatment of refugees and immigrants crossing the border. "His goddamned tweets and lying, oh my God. I'm talking too freely, but you know," Maryanne continued, without a clue her comments would be made public in the future.

It hadn't always been that way, though. Back in the day, Maryanne was one of Donald's biggest cheerleaders. "Six years ago, I had an operation. Donald came to the hospital every single day," She told New York magazine in 2008. "Once would have been enough — the duty call. That's how love shows when you go that extra yard." Maryanne also credited Donald with helping secure her nomination to the U.S. District Court. "There's no question Donald helped me get on the bench. I was good, but not that good." Maryanne is quoted in the book "The Trumps: Three Generations That Built an Empire."

Maryanne Trump Barry assassinated Donald's character

Maryanne Trump Barry made her thoughts about Donald Trump clear during her conversations with Mary Trump. "He's as tight as a duck's a**. Just like dad was," was one of the nicer sentiments. Although, nothing surprising there. "[Trump] is the cheapest S.O.B. I've ever met," Former New Jersey Gov. Chris Christie told Politico in June 2023. "What Donald Trump is good at is spending other people's money."

"He was a brat. I did his homework for him," Maryanne said, claiming Donald only got into UPenn because somebody took his "SATs or whatever. ... That's what I believe." She contended that Donald never read and was often cruel. Maryanne said he was only out for himself, and the one thing he achieved on his own merit was his multiple corporate bankruptcies. Maryanne also admitted that she and Donald had a falling out over their father's will, which resulted in the petulant former president not speaking to her for two years. She also said when Donald spoke at their father's funeral in 1999, he only talked about himself and his achievements.

Apparently, Maryanne's comments caused a new rift between herself and her brother. "As is the way it often is with thin-skinned Donald, when he heard about some of the things his older sister said about him to Mary Trump, he got bent out of shape, and they cooled the relationship," a source close to the Trumps told People in November 2023.

Maryanne Trump Barry mauled 'Madonna' Ivanka

Maryanne Trump Barry didn't save her venom just for Donald Trump; his oldest daughter, Ivanka Trump, was also on her hit list, and it's safe to say Maryanne wasn't a great fan. She shared her thoughts on Ivanka during her conversations with Mary Trump. But this time, MSNBC's "The Reid Out" obtained a copy of the secretly taped chat.

Maryanne and Mary were talking during the time of the Trump administration's "zero tolerance" refugee separation policy that resulted in over 5,000 children being removed from their families, per PBS. During the traumatic and heartbreaking ordeal, Ivanka posted a completely tone-deaf photo on X, formerly Twitter, of herself holding her son. "My [heart emoji] #Sunday Morning," she captioned the pic.

"When that d*** Ivanka puts this picture of the Madonna and child on Instagram when the big news of the day was how kids are being ripped from their families. I couldn't blame — I'd never heard of Samantha Bee before. I couldn't blame what she said," Maryanne told Mary, referring to the comedian branding Ivanka "oblivious" and a "feckless c***." Maryanne continued her onslaught against Ivanka, claiming, "She's all about her" and calling her a "mini Donald." Maryanne said Donald's "Besotted with her. He always has been. She's always been his favorite." Maryanne also dissed Donald's third-born, Eric Trump, claiming he'd "become the moron publicly."

Maryanne Trump Barry resigned over a tax scam investigation

Maryanne Trump Barry's shady side wasn't restricted to talking trash about members of her family. She had some skeletons in her own closet, too. The New York Times reported in April 2019 that Maryanne stepped down as a federal appellate judge, which ended an investigation into whether she broke judicial conduct rules by conspiring with family members to commit tax fraud.

The Times claimed that Donald Trump and his siblings engaged in multiple shady tax schemes and fraudulent actions to inflate wealth and evade inheritance taxes following their father Fred Trump's death in 1991. As a judge, Maryanne was allegedly able to help facilitate her family's reported fraud and personally benefit financially, too.

Many were not happy about Maryanne seemingly evading justice by retiring. "If the Times story is correct, then she participated in a decades-long multimillion-dollar tax fraud. That should be an impeachable offense," attorney Scott Shuchart, who filed one of the ethics complaints against Maryanne, told the AP in April 2019. "I think it's appalling that we're continuing to pay this criminal and that she now has completely avoided consequence."

Maryanne Trump Barry gave up on Donald

Maryanne Trump Barry and Donald Trump's rollercoaster relationship took a nosedive following the release of 15 hours of secretly recorded conversations between Maryanne and her niece, Mary Trump. Mary used much of the recorded material for her scathing 2020 tell-all "Too Much and Never Enough: How My Family Created the World's Most Dangerous Man." Still, Mary's spokesperson, Chris Bastardi, told The Washington Post that his client had started taping the chats with her aunt to use as evidence in a lawsuit over her inheritance.

Regardless, it seems the tapes captured only a slither of Maryanne's true feelings about her younger brother. "She thought he was born without empathy for others and was basically a ruthless and selfish businessman without character," a source told People. "She basically didn't trust much of anything he did in business or politically."

Another insider said Maryanne had all but given up on Donald by the time of her death. However, she remained loyal to him by not publicly talking badly of him, and she never officially commented on the tapes. Still, once her thoughts had become public, it was pretty much game over between the two siblings. "Once you have stabbed Donald in the back, it is hard to get back in his good graces, but for a family member who can offer him something, or who has something on him, he is more forgiving," another source told People.