Dr. Peter A. Olsson is a retired physician, psychiatrist, and psychoanalyst who believes that Donald J. Trump is often misunderstood, difficult to love, frequently resented, despised, and feared, but is begrudgingly respected by his political enemies. President Trump is disliked by many Americans, including most psychiatrists, psychoanalysts, psychologists, and mental health professionals. Many in these professions have written extensively about Trump's personality and psychology, but few have been complimentary or even objective toward him. My psychological study attempts to be fair and balanced. I have never formally interviewed or clinically examined Donald Trump, nor have I done a formal mental status examination. However, I have observed his political, verbal, and nonverbal behavior. I have read his books and many of my colleagues' observations, opinions, and theorizing. Traditional applied psychoanalytic theorizing or academic political science approaches do not give an accurate picture of President Trump. His elusive and choppy free associative verbal style is both evocative and provocative. He can be defiant, bombastic, and emotionally hyperbolic. Trump's controversial, unorthodox, and powerful wheeler-dealer businessperson approaches to politics, political campaigning, and governing drive traditional psychological and political science experts to distraction and even narcissistic rage. Like all of us, Donald Trump has flaws. The tragic flaw of his personality is an obsession with winning at any and all costs. One truth that seems to elude Donald Trump is that you can learn from defeat. (About the Author) Peter A. Olsson, MD, grew up in Brooklyn and Queens, New York, near where Donald Trump grew up. After medical school and psychiatric-psychoanalytic training at Baylor College of Medicine in Houston, he practiced and taught psychiatry and psychoanalysis in Houston for 25 years, and then taught for 20 years in New Hampshire.