Fred ‘Freddy’ Trump, Jr. : 5 Fast Facts You Need to Know

One little known story and tragedy in Donald Trump’s family history involves his older brother, Fred “Freddy” Trump (second from left above, next to Donald Trump, who is on the far left). Freddy Trump died young after struggling with alcoholism throughout his life, and the president watched as the bottle destroyed his brother’s promise.

“He just had everything,” Donald Trump has said of Freddy, calling his brother the “best guy.” Freddy Trump was an alcoholic who died before his brother’s fame reached its pinnacle. Donald Trump has used the story of Freddy’s alcohol addiction as president to highlight the dangers of opioid abuse. “I learned because of Fred…If we can teach young people and people generally not to start, it’s really, really easy not to take them,” President Trump said of drugs.

The New York Times called Freddy Trump “a handsome, gregarious and self-destructive figure who died as an alcoholic in 1981 at the age of 43.” Freddy could have been the heir apparent, and he might have been were it not for his affliction. Donald Trump was the second oldest son in the family, after Freddy, said The Times. Trump has three other siblings – Robert, Elizabeth, and Maryann. Freddy Trump is also the reason for an interesting detail in Trump’s personal biography: The president says that, because of his brother, he has never had a drink of alcohol. However, after Trump’s father died, the president and Freddy’s heirs battled over Trump Sr.’s will.

Here’s what you need to know:

1. Freddy Trump Urged Donald to Never Drink Alcohol & the President Followed His Wishes

Trump has repeatedly revealed that Freddy advised him not to drink.

“He would tell me, ‘Don’t ever drink. Don’t ever drink,’” Donald Trump told Newsweek. Trump imparted the same advice to all of his children, saying of Freddy, “He was a great guy, a handsome person. He was the life of the party. He was a fantastic guy, but he got stuck on alcohol. And it had a profound impact and ultimately [he] became an alcoholic and died of alcoholism. He would tell me, ‘Don’t drink ever.’ He understood the problem that he had and that it was a very hard problem.”

As a result of Freddy’s alcoholism, Donald Trump abstains from alcohol. Trump also avoids drugs and cigarettes, says People Magazine. Trump also spoke about Freddy to Anderson Cooper:

Donald Trump told Christian Broadcasting Network in an interview that Freddy “had everything going, but when he went to college for some reason he started drinking. That was before the drug age and before the other things…but he drank and he drank a lot and he started drinking more and more and he ultimately died of alcoholism.” As a result, Trump told CBN, “I never drank.” He called it a “defining moment.”

Trump addressed Freddy in an emotional press conference on opioids in October 2017, saying, “I had a brother, Fred. Great guy. Best looking guy. Best personality. Much better than mine. But he had a problem. He had a problem with alcohol. And he would tell me. ‘Don’t drink. Don’t drink.’ He was substantially older, and I would listen to him. And I respected (him)…he would also add ‘don’t smoke,’ and he would say it over and over and over again,” the president said. “And to this day, I have never had a drink, and I have no interest in it. And to this day I’ve never had a cigarette… There’s plenty of bad things too. He really helped me. I had somebody who guided me. And he had a very, very tough life because of alcohol, believe me. Very, very, very tough life. He was a strong guy, but it was a tough, tough thing that he was going through… but I learned because of Fred. I learned. That’s what I think is so important… If we can teach young people not to take drugs. Just not to take them.”

2. Freddy Trump Was an Airline Pilot & Married a Flight Attendant

Freddy Trump was known for his free-spirited personality, and his love of flying airplanes and fishing. In some ways, the brothers are contrasts. The New York Times called Freddy Trump a “a fun-loving airline pilot with a gift for imitating W. C. Fields.” Town and Country Magazine noted, “Fred Trump was the second oldest of Donald Trump siblings. (Maryanne Trump Barry, a federal judge, is the eldest, followed by Freddy, Elizabeth, Donald, and Robert, who also worked in the family business.) Born eight years before the president, he also worked briefly for his father in the family real estate business but left to become a pilot.”

Freddy Trump also had a love for deep-sea fishing. In interviews about his brother, Trump brings up Freddy’s love for flying again and again. Freddy was a “free spirit,” says The New Yorker. Freddy married and then divorced an airline flight attendant, and he was Trump’s best man at his wedding to his first wife, Ivana, UK Daily Mail says. Freddy had two children, Fred and Mary, who were named for his and Donald’s parents, Daily Mail says.

Harvey Levin of TMZ interviewed Trump after election day, and the subject of Freddy came up. “We talked about his brother’s death and his fear that he might become an alcoholic because he might have a gene. You rarely hear him describe his own fears,” Levin told The Washington Post. In a sense, Trump lets his guard down the most – he is at his most personal and real – when he discusses Freddy.

Trump has become emotional about Freddy in multiple interviews. When Megyn Kelly asked him what had hurt him emotionally during the course of his life, he responded, “Well, I think the big thing would be, maybe, the death of my brother. That was, you know, the hardest thing for me to take. That was very tough because, you know, it’s unnatural. And he saw a certain potential in me.”

3. Freddy Trump Was Originally the ‘Heir Apparent’ to the Trump Fortune

Donald Trump with his father after his graduation from Wharton School of Finance. (Facebook)

Donald Trump with his father after his graduation from Wharton School of Finance. (Facebook)

As the older brother, Freddy Trump was the one in line to inherit the family empire, said The New York Times. Donald Trump told the Times that his brother Freddy “was caught sort of in the middle as somebody who didn’t really love [the family business], and only because he didn’t really love it, he wasn’t particularly good at it. My father had great confidence in me, which maybe even put [more] pressure on Fred.”

Trump has described himself as his brother’s opposite, The Hill says, and he has described Freddy Trump as a “peacemaker.” As Freddy gravitated to flying, Trump followed in his father’s real estate footsteps.

4. Donald Trump & All of His Siblings Were Groomed to Be High Achievers By Their Demanding Father

Fred Trump, Donald Trump's father

Fred Trump, the father of Republican presidential candidate Donald Trump, in an undated photo. (Wikipedia Commons)

Key to the story of Donald Trump and his brother: Their hard-charging father, Frederick Trump, who built a real estate empire, Yahoo says.

Freddy didn’t have the drive of Donald, who was eight years younger, and he felt that he couldn’t match up to his father’s perfectionism, said Yahoo. Yahoo says that Fred Sr.’s criticism “motivated” Donald but helped drive Freddy to drink. The site quoted Stephen Bank, PhD, co-author of The Sibling Bond and an adjunct professor of psychology at Wesleyan University, as saying the differences between siblings sometimes becomes highlighted because of the internal family dynamic. “It’s called deviation amplification — there’s a multiplier effect of how different they are,” Bank told Yahoo Parenting.

5. Freddy’s Heirs Battled With Donald Trump Over Fred Sr.’s Will

Donald Trump with his father, Fred.

Donald Trump with his father, Fred.

All the president speaks with love and empathy of Freddy in public, there was family acrimony over the patriarch’s will, and ugly allegations flew around. Yahoo says Fred’s heirs were cut out of Donald’s father’s will, and Donald helped craft it, causing acrimony. Fred Sr. left $20 million when he died in 1991, but his will specifically excluded Freddy’s children, said The Hill.

Freddy Trump’s children sued, arguing that Trump and his siblings were responsible for excluding them from the will and arguing that Fred Sr. had dementia and didn’t know what he was doing, the Hill said.

Trump has said the suit was settled “amicably” but not before he withheld medical care from his brother’s sick child, according to The Daily Mail. According to The New Yorker, Trump “cut off benefits from the family health plan that were paying for the medical care of his nephew’s seriously ill young son.”