Background Work on President Trump and the Law

Trump had a long and varied life before he started entering public life as a presidential candidate.  Did he have any run-ins with the law when he was growing up?  Has he ever been charged with a crime?  In business or otherwise?  What do his years doing business tell us about him and the law?
I'll offer a "Joe Amateur" answer to the question, taking info from USA Today, Wash Post, radio news, my own impressions.  There could be mistakes.  (actually I just did what Pres. Trump can't seem to do in public).  If I go on doing blogs or otherwise investigating this subject, I reserve the right to correct some of my generalizations and claims in this early round.

Trump mainly through business has been involved in thousands of legal cases.  I believe the same article pointed out that for Hillary Clinton the figure was something like 900.  I feel fairly safe in saying that Trump says, in general, things about these lawsuits that are frequently contradicted by reports from other sources.

When he was a kid, how was Trump at following the rules?
According to Valerie Strauss, education reporter at the Washington Post (July 17, 2015) "Behavior problems led to Donald’s exit from the [junior high] school, at which point he was sent to the New York Military Academy at age 13 by his parents, who, according to Biography.com, hoped 'the discipline of the school would channel his energy in a positive manner.'  It sounds like they were really worried he might become a flatout "spit in your face rebel," a term I think I invented here and now.   I guess, then, that even at age 13 he had a hard time following rules made by others, so they sent him to a military school that would slap him around if he didn't obey.   Strauss' article is titled, "Yes, Donald Trump really went to an Ivy League school"--Univ of Pennsylvania in Philadelphia.  He was like George Bush, Jr, who had decent grades but made it into Yale because his family was one of the richest in Texas.  The person who interviewed Trump at U Penn, to decide whether to let him in, is said to have been a friend of Trump's older brother.

Later I may read to learn the real answer, but let's do a thought experiment on what happened when Trump at military school, based in part on what I was like at that age.

There seem to be two basic options:  Either Trump liked going there and took up gladly the role of playing military school, or he resisted it.  If he liked it, he dove in and did a lot of swimming others told him to do because it was more fun than splashing in the shallow pool of his previous life.  Also, he may have liked it because it got him away from his parents.  When I was at home around age 16, my dad or mom would lay down the law and I'd go in my bedroom and say without making sound, "I HATE YOU!"  Just scream it in a whisper at the walls.  And I was a rule-obeying kid; Trump hadn't been.
If Trump resisted it, he had two choices: fight or surrender.  My example just given was surrendering but wanting to tell the adults to go ---- themselves.  If Trump chose to fight, he soon learned the military school officials were bigger than he was and united against him.
Either way the whole episode could easily have been one factor leading to a man who didn't have much regard for rules imposed on him by others. 
 

What can we tell about his personality that gives hints at how he would relate to the law?
Trump is obviously a huge success in business and making money, and in many related parts of life.  Huge success in being charming and being liked, and a huge success with women.  He had a headstart with the family he was born into, but he has worked super-hard and has scratched his way to the top.  He's lost big and fought hard and come roaring back.  He's a real big winner in those parts of the game of life.
I don't know how else to put this, so let's imagine that there are 202 "basic important facets" to life on Earth.  Donald Trump is one of the 100 most successful people in the US, or say the world if you wish, in maybe 20 of those 202 areas.  If I'm one of the 1000 most successful persons in even one category, what would it be?  Winning high school cross country races?  I won the state in cross country, and it was a little state.  Letting go of negative feelings?  because I've been trained in that for 30 years and done it a lot.  These are areas that sound like they might not even be on the first 202 areas of human endeavor, right?

Trump is about as successful as any human seems to be able to be, even before his political success.  Now he's the most famous person on Earth and the most powerful.  Yet when he talks about areas where he isn't in the very top group, what does he do?  He exaggerates his own level of achievement, time after time.  I've never been told of his admitting a mistake.  His inaugural crowd is the biggest, even though photos showed it was not.  He was voted against by more illegal voters--3 million--than anyone ever, even though there's no evidence that maybe more than 100 or 1000 people voted who shouldn't have, and got their votes through.  Children under 10 stop reading here.  He has the biggest dick and doesn't have good enough judgment to keep from talking about it in public.  That kind of talk, all by itself, would have killed any number of previous presidential candidates.  He says he graduated first in his college class, even though the program for his graduation doesn't say he received any level of honors.  He graduated average.  I graduated average from paralegal school--no honors.  I don't put that on a banner people can read on my bumper sticker, but if the subject comes up, what I say can be verified by the records kept at the time by people other than me.  People who had no particular reason to be biased against me and falsify records, people whose jobs depended on their keeping fair and honest records.

This is hard for Trump because he's used to making a huge effort and muscling his way to the top, financially, socially.  He's used to putting the full-court press on women and having a solid percentage of them lean back on the couch and lift open their thighs for him.  Very intoxicating for most men who succeed a lot with that.  He's used to dating and marrying models.  He's used to declaring a sort of holy war on those who end up opposed to him.  A perfect example of this is his campaign slogan "I'll put her in jail!" about Clinton.  Oddly, within days of being president-elect, he mysteriously learned there was nothing to put her in jail over, or the FBI would have already been working on it for him.

Tell me if I'm oversimplifying, as if anybody reads this stuff (no comments, I think, by anybody but me so far--32 posts or so), but he kinda has to be right all the time.  Here's an example:  Trump believes torture works to produce good information, so he checks with people in the field and reports back that he has been told that torture works.  Recent studies show that he could have easily stumbled into someone in the field who thinks torture produces myth-making, because there are lots of those people.  But Trump finds someone who proves him right.  We're all like this to a point, but only President Trump and candidate Trump, among people on that level, says awful things about judges who rule against his side.  He can't stand to have anybody make him wrong.  Goes bonkers.  His own Supreme Court nominee, Neil Gorsuch, tells the press that Trump's saying things like that is a horrible thing for a public official to do in a democracy relying on an independent judiciary.

Tentative conclusion:  Mr Trump looks like a person, a candidate, and now a president whose Achilles heel could be his relationship with the generally agreed-upon rules of society. Perhaps the most formal and organized of such sets of societal rules is the rule of law.  To some extent he can skate above these rules in some areas because of his level of success, because he has always been, since he was about 30, the boss, the rulemaker in his realm.  He is not that now.  Unless he figures that out fast, he's got a long row to how ahead of him.  The country does, too.   Maybe a billion rule-minded people are watching him.  Before, we didn't care what he did, much.

He also seems quite willing to speak up and disagree with things that can readily be determined to be facts, from election results to science to previous news reporting.  Wants to make up his version and have everybody think it's real.