If you are going to read just one (or one more) book about Donald Trump and his character, what drives him, what explains his behavior in all the realms of his life (at least in the ones of which we are aware), I strongly recommend Commander in Cheat: How Golf Explains Trump (Hachette Books, 2019) by the golf writer, Rick Reilly, associated for a long time with Sports Illustrated and ESPN.
Golf has been an integral part of Trump's life since he was a youngster, both as a player and later as a golf-course owner. In both realms of golf, Trump is a master cheat, bully, liar, and tall story teller. Reilly has many illustrations of Trump's behavior, on the course, in the club houses, and in the owner's offices/suites. The book is filled with humor, which makes it an easy read. But of course, the subject is deadly serious and Reilly is serious about his work as a journalist.
By the way, this Is not a gossip book. It is a work of journalism, filled with personal observations, confirmation of the stories told by others from well-known professional golfers, to members of Trump golf clubs, to a variety of amateurs and entertainment types who have played with him, to caddies, both Trump's and other's, and double-checking. It is most revealing about Trump the person, as well as Trump the golfer and Trump the golf-businessman. And, the humor to the contrary not-withstanding, it is a scary book, which I think Mr. Reilly intended it to be.
Mr. Reilly begins the book with a quote from the English author and humorist P.G. Wodehouse : "To find a man's true character, play golf with him." While many a famous person in golf played with him, learned his true character, and still associated their name with his for one reason or another, one of the most famous names in golf, who associated his own name with a variety of golfing and non-golfing products, was once asked by Trump to join in a business venture with him. The man said, "OK. Let's play a round." After it, he just walked away and never spoke with Trump again.
Mr. Reilly ends his book with the following:
"I feel sorry for Donald Trump. I feel sorry for someone who has to juggle that many spinning lies, who has to fight that many endless feuds, who has to cheat and lie and insult so many good people just to stand on a rickety first-place podium that never stops needling rebuilding.
"The truth is, the person in golf Donald Trump cheats the most is himself. . . . In life we're defined by the obstacles we overcome. That's the stuff we hang on our inner wall. But if you cheat to get around those obstacles, you never know the thrill of actually beating them.
"It's like buying a trophy in a pawn shop. You can shine it up and show it off and pretend you won it, but when you get close to it, it only reflects the face of a loser."
And it is to that conclusion that I have come about Trump: he is a perpetual loser, he knows it, and the purpose of everything he does is to cover up that fact from himself, from his followers, and from the public at large around the world. No matter now high he gets --- even to the position of the most powerful single leader-of-government in the world, it is never enough.
Trump has a not-terrible handicap in golf, around a 10, but he has always claimed it is 2 or 3. In story after story from fellow golfers and caddies at all levels he always cheats on his score, whether on his card or in moving or having a cooperative caddie move his ball out of the rough or pull it out of a water trap or move it closer to the hole on the green, in one way or another. He claims around 18 club championships at his own clubs, but those rounds he has almost always played by himself, the first time through on the course after he took ownership of it. His cheating goes from there to stiffing, threatening and bullying investors/members/designers/builders of his clubs, and the communities in which they are located, in a variety of ways, over and over again. (Not to mention keeping 8 goats on his course at Bedminster so that he claims an $80,000 "agricultural" tax exemption.) And on and on.
But why does he do this? He is not a terrible golfer. His golf clubs/courses are not terrible, although they have never made the "Top "." Lists that he claims they have made and he has on occasion called the makers of those lists to threaten them with one bad outcome or another for them if a given course was not included (sound familiar?) BUT he is not a winner, something he has always wanted to be, but never has been, in his own mind ---- and that's what counts.
Think of it. When he as a young real estate investor, given tons of money by his father, when he was claiming it was his. The decade of losses in the 80s. The bankruptcies at Atlantic City in the 90s. The who-yet-knows-what with the Russians and Deutsche Bank since US banks stopped lending to him in the late 90s. Why won't he reveal his income tax records? That's easy: more massive losses, much lower-than-hinted-at net worth (ever notice that Trump does not talk about his net worth, even in the most general of terms?) more bail-outs by who-knows-who, more borrowing-on-top-of borrowing, possibly more illegal campaign contributions (another sign of a loser --- if you are a winner, you don't need to hide them) and of course possibly money-laundering to cover more losses. And might just the perpetual cheater in golf, documented over-and-over again by Mr. Reilly, be cheating elsewhere, as Michael Cohen stated, on, for openers, his tax returns and insurance claims?
And then we come to the Presidency. Only in the United States, with a Presidential electoral system unlike that of any other country in the world, the design of which is a legacy of slavery, could this man become President. And he knows it. And so, he is a perpetual loser, and he knows it. Which can explain virtually all of his actions as President, from the mundane, like wanting to have the number of people at his inauguration faked upwards to his constant focusing on those powers of the office that he can exert by himself, like tariffs and immigration policy, to the exclusion of a large number of other problem-areas that concern the U.S. government, which, however, would require negotiation by the great (ho, ho, ho) deal-maker. (Of course, his racism and how he uses it electorally is the over-riding factor in the design and implementation of his immigration policies.)
The fact that he is a loser, has been one all of his life, and is constantly striving to rid himself of that self-knowledge, which he cannot do any more than he can truly play to a 2-3 handicap on the golf course, if used effectively and efficiently by his Democratic opponent in the upcoming election, can play a major role in beating him.