Every four years, the American people make history-bending choices when they elect a president. The choice amounts to a bet on character. Who will have the right character–the right knowledge, experience, values, and fortitude–to tend to the nation’s needs?
Back in 2016, I was eager to get some answers from Donald Trump, the Republican nominee. As a longtime developer and TV celebrity, Trump had not been involved in any of the major issues of the day. He spoke out occasionally but never had to work through the complexities of war and peace, the economy, the budget, crime, immigration and labor, and more.
To develop a great character for a story, I often advise writers to use a “Character Dossier.” The dossier poses 33 questions about the character’s background, upbringing, desires and passions, conflicts and problems, and more. When you answer these questions, you not only create a great character. You also go a long way to plotting the story.
I realized, after posing 50 questions for the GOP candidate, that the exercise offered a good model for questioning all your story’s characters. It offers a way to go beyond the Character Dossier. After getting the basic information from the Character Dossier, fashion a set of follow-up questions. Go deep. Explore the questions that the character would rather avoid.
In that spirit, here are 50 questions for Donald Trump.
Personal life
1. Can you say something about your relationship with your father and mother? Were they caring and attentive? How did they discipline you? What worked — and what didn’t? In what ways do you model yourself after them — and in what ways do you depart from their examples?
2. What events played the greatest role in your moral development — at military school, Fordham College, Penn, your early years in business, your early years as a celebrity?
3. Why did your first two marriages fail? Did you grow apart? What kinds of mistakes did you make? How have you learned from them?
4. What role have you played in raising your children? What “values” did you seek to instill in them?
5. What attracts you to Melania? What do you talk about with Melania?
6. What is the biggest personal mistake you have made? How have you learned from that mistake? How did you change your behavior as a result?
7. Explain, in your own words, any of the following concepts or parables of Christ:
• Turn the other cheek.
• Love thy neighbor as thyself.
• Jesus turning out the moneychangers at the temple.
• Blessed are the meek for they shall inherit the earth.
• Jesus washing the feet of the prostitute.
• Jesus caring for the leper.
• Christ’s sacrifice on the cross.
• Christ’s sacrifice on the cross.
8. What book most influenced you growing up? Have you read any books in the last year? If so, what was it? How about the last five years? Ten years? Besides The Bible and The Art of the Deal, what are your favorite books?
9. You have bragged for decades of sleeping with as many beautiful women as you can, whether you are they are married or not. Has this behavior ceased? If so, when and why?
10. You characterize the Billy Bush video as “locker room talk.” In the second debate you said that you have not done any of the actions you boasted about with Bush? So you were lying to Bush? What kinds of other topics do men talk about in the locker rooms you have visited? Without naming names, can you talk about how athletes boast about assaulting women? How do the others respond, typically?
11. Just curious: How do you think beauty pageant contestants feel when a lecherous old man enters their dressing rooms when they are changing and sometimes wearing little or nothing? Is it OK for the pageant owner to do this? Why or why not?
12. In one of your attacks on Fox news reporter Megyn Kelly, you said that she had “blood coming out of her wherever.” You have dismissed the idea that you were talking about menstruation. But how can it be decent to conjure images of blood and gore, coming out of wherever, from someone who was simply doing her job?
Psychology
13. Most accomplished people feel no need to brag about their success. You seem to need to affirm your own greatness in every conversation. Why is that, do you suppose?
14. Why do you lie so repeatedly and brazenly? I’m thinking of whoppers (like your five-year birtherism campaign, your claim to see thousands of Muslims celebrating 9/11 in New Jersey, and that you opposed the Iraq war from the beginning) and less consequential lies as well (like your statement that Hillary Clinton was not at Ground Zero).
15. You have criticized a number of women, like presidential candidate Carly Fiorina, for their looks, face, weight, and so on. What exactly do looks reveal about character? What do your looks reveal about you? What does your hair reveal? Your gut?
16. Psychologists say you are a psychopath or a narcissist. Do you see where they’re coming from? Can you define these terms and explain why your behavior does or does not fit these descriptions?
17. You talk a lot about “winners” and “losers.” Can you define these terms, perhaps with examples from history? How do you get to be a winner or a loser?
18. When challenged to state what sacrifices you have made in your life, you mentioned that you started and ran businesses that make you billions of dollars. Hmmm. Back up. Can you define sacrifice? Then can you respond to the question again?
19. Is there anything innate about blacks, Jews, Muslims, Hispanics, Mexicans, Chinese, Russians, and other groups that makes them “good” or “bad”? Or “winners” or “losers”?
20. Do you think America has become too enamored of celebrities and not adequately respectful of quiet, modest people who work hard and care for others? What qualities do celebrities have that we should emulate or avoid?
21. Why did you attack Ben Carson, Jeb Bush, Carly Fiorina, Chris Christie, Marco Rubio, Ted Cruz, George Pataki — actually, everyone — in such personal terms during the GOP nomination contest? Did you really mean it when you called Carson a child molester and Cruz’s father a conspirator in the Kennedy assassination? Did you sincerely believe everything — or anything — you said? Or did these insults simply offer a blunt way to eliminate rivals?
22. Some psychologists say your harshest criticisms of others are really forms of “projection” — that is, that your criticisms actually reflect your own fears about yourself. So for example you called Cruz “Lyin’ Ted” as a way of diverting attention from your cascade of lies and distortions? Do you believe that people sometimes project like that?
23. You have railed against “political correctness,” saying that people need to toughen up and deal with the everyday knocks of life. Yet you have displayed thin skin when other people disagree or criticize you. What gives?
24. Can you see why people might be concerned about your penchant for violence — saying at rallies that “I’d like to punch him [a protester] in the face,” “knock the crap out of him,” and “in the old days [protesters] would be carried out on a stretcher,” and offering to pay legal fees for Trump supporters accused of assault? Do you not believe that people cannot disagree civilly?
Business practices
25. You have acknowledged not paying contractors who do work for your companies. In a debate, you said you didn’t pay them because you didn’t like their work. Did you specify what aspects of their work dissatisfied you?
26. Over the years you have sued people — or threatened to sue — hundreds or perhaps thousands of times. To what extent is that a tactic of intimidation rather than a sincere desire for redress of wrongs?
27. Have you ever worked with the mob on construction projects in New York, Atlantic City, Florida, or other locations?
28. What lessons did you learn from your many bankruptcies? How did you apply those lessons to later ventures?
29. What’s the toughest business problem you have ever faced? How did you deal with it?
Policy
30. Pick any policy issue. Tell us about five variables that make the issue complex and difficult to manage or solve.
31. You say you “know more than the generals” about ISIS and other foreign policy challenges. Name one fact or insight you can offer that “the generals” do not know or appreciate.
32. How would a wall along the Mexican border prevent people from coming into the U.S. from other entry points? Also, are you aware that there is now a net migration of Mexicans out of the U.S.? Will your wall keep those Mexicans in the U.S.?
33. In your campaign announcement, you called Mexican immigrants rapists and killers but acknowledged that “some of them” might be good. Can you talk about the “good ones.”
34. You have stated repeatedly that you want to create a “deportation force” to locate and remove 11 million illegal immigrants from the U.S. You have also said you would not. Which is the case these days? How would the deportation force work? How much would it cost? What criteria would you use to set priorities?
35. In one of the GOP debates, you said the Trans-Pacific Partnership is stacked in favor of China, which you have identified as the biggest trade threat to the U.S. Now you know (right?) that China is not part of the TPP. So what countries does the TPP involve and what provisions of the pact undermine U.S. interests?
36. Can you explain how currency manipulation works — and how the markets may or may not “correct” for it with changes in exports and imports?
37. You say you will “bring back” manufacturing jobs from overseas. Just how might that work? Given companies’ investment in billions of dollars worth of factories, would you expect them to shut those facilities down and build new ones in the U.S.?
38. Do you really believe that NATO — which won the Cold War and has kept the peace in Europe for decades — is a waste of money?
39. Do you really believe that adding more nuclear powers — Japan, South Korea, even Saudi Arabia — would make the world safer?
40. You say that American companies planning to move their operations overseas would face a major tariff on goods they sell to the U.S. Could you do that unilaterally? Would that possibly provoke other countries to slap tariffs on U.S. products?
41. About the nuclear triad: As Marco Rubio explained, when you looked doe-eyed at the mention of the concept, this refers to the readiness of nuclear weapons on land, sea, and air. Can you say something — anything — about some of the complexities of nuclear policy?
42. Given your stated expertise about tax policy, what specific provisions would you alter to prevent billionaires (?) like you avoiding taxes despite being on a “budget” of $450,000 a month?
43. You have said that your tax dodging and lobbying practices — using government to your advantage, to the detriment of others — is just smart business. Where should a business person draw the line? Do you support any limits on special-interest lobbying?
44. Do you favor — or not — the intervention of Russia or other foreign powers in U.S. elections? What would you do to respond to such interference in the democratic process?
45. Just to be straight, you oppose abortion but now (after stating otherwise) would not prosecute and jail women who received abortions. Is that correct? When does life begin? How would you enforce the law?
46. In your outreach to “the blacks,” you have portrayed African American life as a depraved world of crime, violence, joblessness, and fear? Are you ware that the black middle class is bigger then ever before in history?
47. Likewise you have said that crime has raged back to record highs. Are you aware that crime rates are the lowest in decades, even after small upturns in some crime categories in recent years?
48. Your stance on the minimum wage varies. Should it be raised, right now and in coming years? How much and when? Should the minimum wage be indexed to the cost of living?
49. Unions: Pro or con? Name three things that make unions “good.” Name three things that make unions “bad.”
50. Do your business dealings give you insight about how to deal with organized crime, both domestic and foreign? If so, what?
