Trump pressured his alcoholic brother about his career. Now he has regrets.

The Trump siblings - from left, Robert, Elizabeth, Fred Jr., Donald and Maryanne - in an undated photo. 

President Donald Trump remembers coming home in the mid-1960s to read reports on the cost of mops and paint as he prepared to work in the family real estate business. He was astonished to find his older brother, Fred Jr., reading aviation books in hopes of fulfilling his dream of being a TWA pilot.

"Come on, Freddy, what are you doing?" Trump has recalled saying to his brother. "You're wasting your time." Their father berated Fred Jr., saying he wanted to be nothing more than "a chauffeur in the sky," a friend said, instead of running the Trump company.

Fred Jr. was wounded. "It was a lot of pressure," said David Miller, a Lehigh University fraternity brother of Fred Jr.'s who became his lawyer. "He did what he could to run away from it."

Fred Trump Jr.'s dream of flying for TWA ended. He descended into alcoholism and died at 42 years old in 1981.

Now, as Trump speaks about how he will fight the opioid crisis, he has seized on the story of his brother as evidence of his empathy for addicts, saying that he can apply the lessons of that experience to dealing with the calamity of narcotics abuse.

In an extensive interview with The Washington Post, Trump provided what appears to be the fullest accounting he has ever given of his brother's life and death, and he went further than he has before in acknowledging mistakes.

"I do regret having put pressure on him," Trump said. Running the family business "was just something he was never going to want" to do. "It was just not his thing. . . . I think the mistake that we made was we assumed that everybody would like it. That would be the biggest mistake. . . . There was sort of a double pressure put on him" by his brother and his father.

It is rare for Trump to express regret or admit mistakes. But he said his brother's short, tragic life scarred him like no other event, and he said he remains haunted by watching Fred Jr.'s handsome features fade.

A number of Fred Jr.'s friends, who provided The Post with many new details about his life, said the president has too often told the story in a way that put Fred Jr. in the harshest light while painting himself as the virtuous brother who avoided alcohol. The president was asked to respond to their comments and recently did so.

Jack O'Donnell, a former Trump casino executive who later ran an Arizona addiction treatment center, said the president still has not come to terms with his brother's life and death.

"It always felt like it was a dark family secret, and a subject [about] which he did not want to talk," O'Donnell said. "There is generally a lot of shame around addiction, which is sad. I think the entire Trump family suffers a great deal of shame and unresolved trauma over Fred Jr.'s death."

Tall and handsome

Freddy, as everyone called him, was the firstborn son, so he was given the name of his father. His friends said in interviews that he was the opposite of Donald Trump - soft-spoken, playful, and often joking.

The Trump children grew up in Queens, eventually moving to a two-story, columned house in Jamaica Estates that looked as if it belonged on a Southern plantation. Freddy took the subway to St. Paul's, an Episcopal high school in Garden City, New York, and his father hoped he would be accepted into the University of Pennsylvania's Wharton Business School. But Fred Jr. didn't get in, and he went instead to Lehigh University in 1956, leaving behind his then-10-year-old brother Donald.

Fred Jr. quickly became one of the most sought-after students at Lehigh, and many fraternities courted him. Despite being raised Presbyterian, he joined a fraternity that historically had been Jewish but was open to people of other faiths. One of the brothers said Fred Jr.'s joining that fraternity, Sigma Alpha Mu, was a declaration of his independence from his father.

The fraternity brothers said they never saw Fred Jr. drink excessively, and they recalled giving him the responsibility of house steward, which involved overseeing the kitchen and some finances. Tall, blond and movie-star handsome, he was considered the campus jokester, arranging stunts and carrying himself as happy-go-lucky and wealthy. They recalled him offering them rides in a sports car, boat and an airplane, which he rented at a local airport.

"Every year he would come to college with a brand-new Corvette," said fraternity brother Ira Jay Kirschner. "He was a fun-loving person who enjoyed life."

"He was as far from Donald's personality as you can get," said fraternity brother Mel Bergstein.

After graduating from Lehigh in 1960, Trump met a flight attendant named Linda Lee Clapp, and they married in 1962.

The couple lived in New York, where Fred Jr. relented to pressure to go into the family real estate business. It was Fred Jr., one friend said, who came up with the idea of naming a set of high-rise apartments near Coney Island as Trump Village, the first time the family name appeared on a development. But he soon got into fights with his father over seemingly mundane decisions, such as how much to spend on windows.

Trump pressured his alcoholic brother about his career. Now he has regrets.

The Sigma Alpha Mu fraternity's page in the Lehigh University yearbook in 1960. In the group photo, Fred Jr. is in the bottom row, third from the right. 

Donald, who had been sent to military school to have discipline instilled in him, was about to attend Fordham University. It was in this period that Fred Trump Sr. and Donald Trump chastised Fred Trump Jr. for not wanting to be involved in the family business.

Fred Jr. saw flying as an honorable profession, his friends said. He applied to be trained as a pilot for TWA and passed a rigorous set of requirements to enroll in a 1964 class of about a dozen students. He flew for a number of months as a secondary pilot.

"What he loved doing was flying airplanes," Donald Trump said. "I remember being at the house and other pilots from TWA would come to the house and they'd come to work with Fred because he was a very natural talent."

Three pilots who trained with Fred Jr. said in interviews that they saw signs of his alcoholism emerging. The pilots said they didn't know anything about the pressure Trump was under from his family to join the business, but they said he clearly was under stress that he could not handle.

Bob Dedman, who said he sat next to Fred Jr. at the TWA flight school, said he was "always nattily dressed, polite, educated and well-mannered. A nicer gentleman you will never meet. His problem was he had a major drinking problem. . . . He would go to a restaurant and have a couple of martinis. He would fall asleep and I said, 'Hey, Fred, wake up!' "

By some accounts, Fred Jr. was fired from TWA after a year-long probation for new hires. He was "terminated because he had a drinking problem," said Bob Kavula, vice president of the TWA Retired Pilots Association. "His drinking got in the way of his flying, and they couldn't afford that."

But one of Fred Jr.'s friends, Annamaria Forcier, who as a teenager in 1958 moved to the Queens neighborhood where the Trump family lived, thought Fred Jr. left TWA because of the pressure from the family.

"My impression of it was that he was basically forced to go work for the family firm," she said. "There was a lot of tension between not only the old man but also between him and Donald. There was a lot of tension because they didn't want him to be an airline pilot."

Forcier saw the brothers together on several occasions, including a dinner at her home where she said Donald Trump yelled at his brother.

"I'm five-foot-eight and I'm standing between them," Forcier said. "[Donald] was yelling at him. He was a finger pointer, and he put his finger in his brother's face." Finally, Donald Trump stormed out, slamming the door behind him, she said.

Trump said, "I actually don't know if I ever argued with [Fred Jr.], other than to sort of tell him, 'Gee, you should love this, this business; we can do something great here.' "

Still, Trump has said for years that watching his brother's downfall was instructive, particularly his backing down in the face of their father's scolding. Donald Trump shaped himself in a way that is now familiar: pushing back against anyone who questions him and becoming the kind of "killer" his father wanted to run the family business.

"I stood up to him," Trump wrote in his autobiography, "and he respected that."

Drinking worsens

For a while, Fred Jr. tried to build his own business, establishing an employment agency, but the effort foundered. By 1966, he had rejoined the family company, where he was identified in newspapers as vice president, and became the spokesman for the family's effort to redevelop Steeplechase Park on Coney Island into a zoo-like attraction.

Donald Trump, meanwhile, was increasingly seen by their father as the heir apparent. Donald had completed two years at Fordham University and was under pressure from his father to transfer to Penn's business school, which Fred Jr. had failed to get into a decade earlier.

As it happened, one of Fred Jr.'s closest friends, a high school classmate named James Nolan, had become an admissions officer at Wharton. As recently reported by The Post, Fred Jr. asked Nolan to interview Donald as a candidate for admission.

Nolan said in an interview that he agreed and gave Donald a rating that qualified him for admission. Donald was granted entrance as a transfer student, enabling him to achieve what his brother had not and establishing him in their father's eyes as more successful.

A few years later, when the New York Times ran a feature about the family business, it showed Fred Trump Sr. surveying company property alongside Donald Trump. Fred Trump Jr.'s name no longer appeared in stories about the family business, and his drinking became worse.

"I tried many times to tell him to get help, to try to get him to stop," Miller, the fraternity brother and lawyer, said in an interview at his New York City apartment. "If I had known of the existence of Alcoholics Anonymous, I would have dragged him by the throat to it."

Finally, Miller persuaded Fred Jr. to see a psychiatrist. Miller described the meeting as follows:

"I don't want to stop drinking," Fred Jr. said.

"I can't help someone who doesn't want to stop," the psychiatrist replied.

Miller concluded that his friend simply "liked to drink" and "became addicted to alcohol."

Around this time, Linda decided to seek a divorce because of Fred's drinking, Miller said. They divorced in 1970. Fred Jr. worked at some modest jobs for the family company as his health worsened.

By the late 1970s, Donald Trump's life was being chronicled in the press like that of a celebrity. He partied at Manhattan's Studio 54, married his first wife, Ivana, and began developing property in Manhattan with the financial support of his father.

Fred Jr., meanwhile, was gaunt, ill and hospitalized.

Nolan, the former high school classmate, visited Fred Jr. in the hospital during this period, and part of his stomach had been removed, apparently because of damage from drinking.

"He was melancholy, understandably," Nolan said. Yet somehow the old jokester had kept his sense of humor.

"He said, 'You know, I should have become a comedian,' " Nolan said.

Donald Trump said that he, too, visited his brother at the hospital. He asked his brother what attracted him to alcohol.

"I used to ask, 'Is it the taste, or what is it?' " Trump said in the interview. "He didn't know what to say about it because, frankly, it was just something that he liked."

In these last years of his life, Fred Jr. lived once again at the Jamaica Estates home. Donald Trump has long said that his brother helped him by warning him against alcohol, but he had not said what, if anything, he did to help his brother. Asked in the interview whether he did anything to help his brother fight the disease, Trump said he often traveled from his Manhattan home to visit.

Campaign 2016 I Love New York

This April 8, 2016 photo shows the stately columned home where Donald Trump grew up, in the Jamaica Estates neighborhood of the Queens borough of New York.

"I dealt with it," Trump said. "We went out to dinner a lot. I'd sometimes come home and go to lunch with him."

Asked whether his brother was ever sent to a rehabilitation program, Trump responded: "He did. A number of times." Asked if he visited his brother, Trump said, "I don't think it was necessarily a stay-over rehab because he lived in the house. I don't remember it as being a stay-over. But I spent a lot of times with Fred."

Trump said that "I don't think there was much we could do at the time . . . . Things have been studied and learned right now that are much different."

During this period, Trump said, he was shocked by his brother's physical decline but also by his determination to survive.

"He was so handsome, and I saw what alcohol did to him even physically . . . and that had an impact on me, too," Trump said. In the end, "he actually lived a long time longer than you would expect."

On Sept. 26, 1981, Fred Trump Jr. was at Queens Hospital Center when he died of a heart attack, which the family has said stemmed from alcoholism.

News of the death was received bitterly by Fred Jr.'s friends. Forcier expressed concern that the family had not provided him with the type of support that might have helped him.

Donald Trump feared addiction to alcohol was a disease that ran in his family and that he would follow his brother if he had a single drink.

"Let's say I started drinking, it's very possible I wouldn't be talking to you right now," Trump said in the interview. "There is something about the genetic effect." (Trump noted that his fear of alcohol did not prevent him from buying in 2011 what became known as Trump Winery in Virginia, now operated by his son Eric.)

With Fred Jr.'s death, the family's focus turned even more to Donald Trump, whose fortunes were ascendant as he developed Trump Tower in Manhattan.

Estate fight

Fred Trump Sr. died 18 years after his namesake son. The family of Fred Trump Jr. had hoped to receive a share of the estate similar to what would have gone to him if he had lived.

The issue was important to them because Fred Jr.'s son, Fred Trump III, had a son, William, with cerebral palsy. The boy's care had been covered by a Trump company, but it was costly, with expenses that would last a lifetime.

Trump Inheritance Taxes

In this Feb. 9, 2017, file photo, a portrait of President Donald Trump's father Fred Trump, and three un-signed Executive orders are seen in the Oval Office of the White House in Washington. (AP Photo/Pablo Martinez Monsivais, File)

After the patriarch's death, however, the descendants of Fred Jr. learned that they would receive only a portion of the amount they had expected. They took the extraordinary step of suing several other members of the Trump family in March 2000, alleging that Donald Trump and his siblings had persuaded Fred Sr. to change the will. Donald Trump responded by cutting off the family company's payments for the care of Fred Trump III's child with cerebral palsy.

"When [Fred Trump III] sued us, we said, 'Why should we give him medical coverage?' " Donald Trump told the New York Daily News at the time.

Fred Trump III, referring to Donald Trump and two of his siblings, who were executors of the estate, said in a Nassau County court case that "my aunt and uncles thought nothing about taking away my critically ill son's coverage in an attempt to browbeat me in to abandoning my claim in the probate contest."

In response, Robert Trump, speaking for himself as well as brother Donald and two sisters, said in an affidavit that the health care provided by the family had been given "out of the goodness of our hearts" and was not a contractual obligation. Moreover, Robert Trump said, Fred Trump III received $200,000 annually in gifts and payments from the Trump family "without lifting a finger."

The estate case was settled confidentially in 2000.

President Trump, asked about the dispute by The Post, cited the settlement and said, "One child was having a difficult time. It was an unfortunate thing. It worked out well, and we all get along."

Linda Trump and her two children, Fred III and Mary, declined interview requests. Robert Trump and his sister, retired U.S. appeals court judge Maryann Trump Barry, could not be reached for comment. Elizabeth Trump Grau, the president's other sister, declined an interview request.

'Much nicer guy'

Over the years, Donald Trump has refined the narrative of the impact of his brother's death.

Trump told Playboy magazine in 1990 that his brother's death had shaped his life.

"His death affected everything that has come after it," Trump said. "I think constantly that I never really gave him thanks for it. He was the first Trump boy out there, and I subconsciously watched his moves. I saw people really taking advantage of Fred and the lesson I learned was always to keep up my guard one hundred percent, whereas he didn't. He didn't feel that there was really reason for that, which is a fatal mistake in life."

Speaking that same year in a CBS interview, Trump again came close to putting some of the blame on himself, while still hedging. "Perhaps it was my fault and perhaps my father's fault for egging him on to business because he wasn't good at it, because he didn't like the business," Trump said. He said his brother "totally gave of himself and he gave himself to other people" and was open. "I tend to be just the opposite." He told CNN that his brother was "a much nicer guy than me, to be totally honest with you."

Now, nearly 38 years after Fred Jr.'s death, Donald Trump said that he understands the circumstances of what happened to his brother "much, much better" and that his presidency has given it new meaning. Trump said he would apply the lessons to the fight against addictions, including alcohol and opioids.

"I guess you could say now I'm the chief of trying to solve it," Trump said. "I don't know that I'd be working, devoting the kind of time and energy and even the money we are allocating to it. . . . I don't know that I'd be doing that had I not had the experience with Fred."

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The Washington Post's Alice Crites, Julie Tate and Magda Jean-Louis contributed to this report.

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