Too Much and Never Enough

In the book’s opening chapter, Trump discusses in detail the family dynamics that were present between her grandparents and her aunts and uncles when they were young. She frames the chapter around the 23-room house that Fred Trump Sr. built for his family in the Jamaica Estates neighborhood of Queens in New York City. The author begins the chapter with an anecdote about her aunt Maryanne finding her mother covered in blood and unconscious in one of the mansion’s bathrooms. The elder Mary Trump survived but needed an emergency hysterectomy, which led to an abdominal infection and further long-term complications. Whereas Mary was “often unstable and needy” because of her illness, Fred Sr. “seemed to have no emotional needs at all” and focused on what was important to him (23-24). The author refers to her grandfather as a “high-functioning sociopath” (24), and she explains that the emotional unavailability of either parent had a devastating psychological effect of on the youngest of the Trump children, Donald and Robert. She argues that Donald’s personality traits of narcissism, bullying, and grandiosity are the direct result of the deprivations he suffered (26).

In the second half of the chapter, Trump discusses her family history and how her grandfather became a wealthy and successful developer. She explains that her great-grandfather, Friedrich, came to the US from Germany in 1885 “in order to avoid mandatory military service,” but he died of the Spanish flu in 1918 after fathering three children (29). Faced with being the man of the house following his father’s death, Fred Trump Sr. studied the building trade and began building and selling garages while still in high school. In 1936, Fred Sr. married Mary MacLeod, whose immigration to the US six years earlier from Scotland was “a classic example of ‘chain migration’” (30). By the time the couple had their first two children, Maryanne and Freddy, Fred’s business was booming thanks to his learning how to chase government funding through the Federal Housing Administration. Trump argues that it was clear her grandfather’s “strategy of building on the taxpayer’s dime was a winner” (35).

In Chapter 2, Trump continues her discussion concerning the family dynamics of her grandparents and her aunts and uncles. The chapter primarily focuses on her father, Freddy, who was the second child of Fred Sr. and Mary Trump, and their first son. She explains that Freddy’s natural sense of humor and adventure was suppressed by his father, who expected him to be interested only in what he considered important (40-41). Freddy’s inability to live up to his father’s expectations resulted in harsh treatment and ridicule. Fred Sr.’s lack of respect for Freddy was carried on by his younger son, Donald, whose personality was more like their father’s. Trump argues that Fred Sr. damaged Donald as well, but rather in a way that perverted his perception of the world.

According to Trump, Donald’s “understanding of ‘right’ and ‘wrong’ would clash with the lessons taught in most elementary schools” (44). Donald’s early connection to his father’s worldview eventually led to his personality traits that are evident today—his displays of confidence, his belief that rules do not apply to him, and his exaggerated display of self-worth. She argues that “a large minority of people still confuse his arrogance for strength, his false bravado for accomplishment, and his superficial interest in them for charisma” (44). The author ends the chapter describing how Donald bullied and tormented his younger brother, Robert, and provides an anecdote about an incident that had a profound impact on Donald’s personality. When Donald was seven years old and relentlessly bullying Robert, Freddy dumped a bowl of mashed potatoes on his head in retaliation. The incident caused everyone to laugh hysterically, but it humiliated Donald so much that he came to realize that humiliation could be a weapon. The author argues that “from then on, he would wield the weapon, never be at the sharp end of it” (46).

In Chapter 3, Trump focuses on the relationship between Fred Sr. and Freddy, his oldest son and the author’s father. While Freddy failed to meet his father’s expectations, Donald learned to ingratiate himself with his father by disregarding authority, becoming arrogant, and bullying—all impulses that Fred Sr. identified with. Trump argues that Fred Sr. “liked his killer attitude, even if it manifested as bad behavior” (49). She explains that by 1959, Donald’s behavior at school resulted in him being sent away to a military school, an idea that Fred Sr. went along with only because he was on the school’s board of trustees. While Donald was at New York Military Academy receiving discipline for the first time in his life, Freddy was still being prepared to become his father’s right-hand man.

Freddy’s interests shifted dramatically in college, however. He joined a fraternity, completed the ROTC program, and developed a love for flying. After graduation, he entered the Air Force National Guard and became a fully licensed pilot, but still took his expected place within his father’s company. In the early 1960s, Freddy married Linda while working for Trump Management full-time, and the couple lived at one of the company’s properties. After three years, a rift developed between Freddy and Fred Sr. and Freddy decided to follow his dream of becoming a pilot, even at the risk of his father cutting him out of his inheritance (59). According to the author, Fred Sr. considered it a betrayal when Freddy left, “and he had no intention of letting his oldest son forget it” (59).

In Chapter 4, the author continues to discuss her father’s career and the strained relationship with his father. She explains that Freddy becoming a pilot was unique in that none of the other Trump children “would accomplish so much entirely on their own” (60). In 1964, at only 25 years old, Freddy was one of 12 men accepted into TWA’s first pilots’ class (61). Despite his success, Fred Sr. continued to belittle him and even referred to him as a “bus driver in the sky” (62). On one occasion, Donald and Robert came to visit their older brother’s family at their new home in Massachusetts, but they ended up insulting him by echoing Fred Sr.’s opinion of his new career. By this time, Freddy had developed a serious problem with alcohol and ultimately was given the ultimatum of either resigning or being fired by TWA. He attempted to fly again with smaller airlines, but his drinking problem worsened, and he ended up returning to his father’s business for employment.