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I seriously considered voting for him.People have made a big fuss about xenophobia and racism and bigotry, insults and now major flip-flopping, which certainly matter, and I’ll let others make relevant points on that.I was looking at the more “executive” qualifications since that’s actually the job Trump is asking us to give him. There are lots of jerks and poor excuses for human beings who happen to also be great executives who get things done well and bring great things and needed change. Steve Jobs was not the most adorable personality all the time but he arguably fostered amazingly useful change in personal computing. That overrode the negatives. So I thought to look more at what Trump is like that impacts his ability as an executive. This is what I found:RED FLAG #1: business dealingsThere have been a number of in-depth business media reports on Trump’s many business dealings, and the consensus is it is far from an impressive track record. He’s not the self-made man starting from nothing. Trump has always boasted about getting merely a $1 million loan from his father Fred Trump to start his businesses. But it has been revealed through Trump organization documents that he actually got closer to $145 million, and engaged in fraud to even steal more from his father during his father’s Alzheimer’s years.Trump boasts of being a master at the “art of the deal” but a substantial amount of evidence points to major mistakes and disasters, such as building up not just one casino in Atlantic City that was on shaky financial ground, not two, but three that all competed with each other. What was he thinking??? His father, Fred Trump, had to bail Donald out with a multi-million loan, and that still wasn't enough for the casino businesses to all come crashing down. Why did it crash so spectacularly? The “house” is designed to always win. But Trump had vastly over leveraged the deals and the Atlantic City casino commission even saw this even before he opened the Trump Taj Mahal.UPDATE: I found out Trump actually bragged about how he made a killing on his casinos in spite of their financial collapse, and he did it in two ways:He intentionally shifted ownership to a worthless LLC that passed the loans to another company he set up, thereby shafting the lenders royally.He didn’t pay contractors.In other words, he’s without a shred of morality or decency in business dealings.His steaks, alcohol, clothing, magazine, shuttle, and a number of other businesses have all been failures. Trump University is now headed towards criminal court as the law suits are now including counts of racketeering under the RICO Act which if successful could force him to sell assets for lack of the potential 9-figure penalty.UPDATE: Trump U plaintiffs got a reported settlement of around $25 million despite Trumps boast that he’d never settle.Things only started turning around when his children came on board to help run some businesses and the Trump® brand became the dominant product. It was a clever thing getting out of selling anything but the name, but the worth of that name may be practically zilch after this election if recent polls don’t improve.UPDATE: Nobody seems to be buying the Trump nameplate anymore, and several buildings have actually taken the name off at the insistence of the residents.Some financial media have calculated that if Donald had put his loan from his dad into the S&P 500 and left it there he would have actually done about the same or better. Meanwhile, lots of others in the same business in New York have done much better than Trump.UPDATE: The Southern District of New York is waiting for Trump to get out of office so they can arrest him on charges of fraud relating to his business dealings going a long way back. Specifically, they have evidence of massive understating AND overstating of property value given to a large mansion he owns for the purposes of getting a better insurance rate on the one hand, and getting favorable loan rates, both of which are fraud felonies. These were pointed out by during congressional testimony by Michael Cohen who had direct knowledge of the applications.Trump’s financial ties with Russian oligarchs close to Putin are not public knowledge—yet—but it seems clear that he’s gone to Russia to feed his need for credit. No bank in the West will give him anything anymore. Not good. What’s the deal??UPDATE: There IS evidence, here’s some: Trump and the OligarchThe Russian connections, and his ties to business all over the globe are all huge potential conflicts of interest with the job of President.Donald Trump's foreign ties may conflict with U.S. national security interestsUPDATE: There is now an investigation into the massive amounts of inauguration funding (WAAAY more than any other president-elect) and the foreign people who donated.There is also a very serious investigation into the NRA’s role in funneling millions of dollars from Russia into the Trump campaign. This is, of course, strictly illegal money laundering.UPDATE: The Jeffrey Epstein bromance story before Trump shafted him on a real estate deal (and deeply pissed off Epstein) has yet to be made public but it can only go in the direction of sordid. Trump acolytes and worshipers don’t seem to care.Addendum: Here’s a rather comprehensive panorama of Trump’s businesses reviewed by the son of a banker who had to deal with Trump’s debts: Why do people forget that Donald Trump is a successful businessman?ConclusionThe real art of Trump’s deals seems to be his ability to con others. His mastery of getting others to pay for his businesses while he sneakily shifts responsibility for the debt and weasels out the back door with as much money he can grab before it goes under. This shifting of losses has also been on the backs of numerous contractors who have collectively taken huge losses and many have been forced out of business by Trump’s non-payments. On one property in Florida the liens for non-payment have accumulated to the point where it recently went over the amount needed to force a sale of the property to pay them off.Interesting story: In lieu of paying his notoriously ruthless lawyer Roy Cohn (former advisor to disgraced Senator Joseph McCarthy[1][1][1][1]), Trump once took off his cuff links and insisted Roy have them for his work on a case saying they were diamonds and platinum worth $50,000. Roy kept them until he died. His estate had them evaluated. They turned out to be fake diamonds in a base metal, cheap junk. There was a similar story from another person who Trump owed money, was given cufflinks with the same smooth story about their supposed value; same cheap junk. A perfect example of the Trump way of dealing with people.It’s Trump’s habit to not pay people. Cities in which he wants to hold a rally have had to demand security costs payments up front because he just doesn’t pay after the event, leaving municipal bill of hundreds of thousands to be paid by taxpayers. He’s even doing it to his campaign staff:One secret of Trump's low-cost campaign: free laborIs this also his magic secret sauce for making the country “great again”? Maybe, he’s already floated the idea of “renegotiating” the national debt, which every economist and financial advisor I’ve read on the subject have said is a recipe for economic suicide due to nobody lending to the US again.UPDATE: January 2020: The Federal deficit is about to break the $1 trillion mark, definitely going in the opposite direction FAST that Trump said it would.Interesting note: Trump is known in NYC banking circles as the King of Debt.Update: The coronavirus bailout to businesses which Senate Republicans wrote in secret before even allowing the full Senate to vote on it, and which got shot down twice before finally getting some compromise wording that would at least give some oversight to how the money is used was signed into law by Trump who added a “signing statement” that he would not enforce the oversight of spending that money. Think about that. Most of that money is going to the people who don’t need it: venture capitalists, stock holders, hedge funds.[2][2][2][2]— many of the same people who also caused the 2008 crisis. Dëja vu.There are always ups and downs in business and lots of entrepreneurs start businesses that don’t make it, but there’s just too much wreckage and bad blood in Trump’s business wake. I doubt any major corporation would even consider hiring him as CEO, no matter what the business. I can’t see anything in his business resume that would make me believe that he could ever deliver on his promise to “make America great again.” Certainly not his economic plan which would make George W Bush’s plan brilliant by comparison.Some might say that the December 2017 tax bill unleashed great prosperity. What they don’t say, or don’t know, is that much of the benefit of that tax bill went right to the accounts of the most wealthy who didn’t even need a tax break to survive while virtually nothing “trickled down” to the ordinary workers. It went to stock buybacks, offshore accounts, and other non-investment in the economy. The large majority of economists admit this.RED FLAG #2: words matter, they mean things, except when they don’tTrumps 1987 book “Art of the Deal” was actually entirely written by his ghostwriter, Tony Schwartz, whose name also appears on the book. That’s not the problem, lots of “autobiographies” have to be written by a ghostwriter to make them acceptable for publishing. The problem is that Trump now claims that Schwartz didn’t write it (he wrote every word) which is laughable because Trump had no experience in writing books, and Schwartz was even named on the book. This was yet another bald faced lie in a string of lies and playing loose with facts that continues to grow so fast that the political fact-checkers have been working overtime and haven’t been able to keep up. There are just way too many to list here, and others have tried to list them (See Washington Post’s running count of Trump’s false statements). What is most telling is that Trump has scored the poorest ability to speak the truth of any major political figure the media has covered, by a wide margin.Donald Trump's fileCompare that to Clinton’s which turned out to be one of the most truthful and accurate of all candidates in the primaries, surprisingly even slightly better than Bernie Sanders:Hillary Clinton's file on PolitiFactAddendum:One commenter suggested I edit out what the fact-checking U.S. politics website PolitiFact reveals about Clinton’s record on the campaign trail as “a common misconception and not true.” As a justification, he says, “She knows politics all too well so she can generally navigate in a way that would support that narrative but she scripted and doesn't make herself open to scrutiny. What the commenter fails to understand is 1) you don’t need to be an insider politician to fabricate pants-on-fire whoppers, and 2) fact-checking is an endeavor to set the record straight and is completely unrelated to whether a statement is delivered scripted or off the cuff. As an example of this, we can look at Trump’s scripted speech on immigration which is also generously sprinkled with inaccuracies, skewed facts, partial facts, and downright pants-on-fire false statements. See Trump Still Off on Immigration and the Trump campaign’s Twisting of Clinton’s Immigration Plan. It doesn’t get more scripted than an ad. Note also that Trump’s scripted statements are actually somewhat less littered with skewing and outright fabrications than Trump off-the-cuff because they are not his own thoughts but speeches carefully fabricated for him with some actual research instead of Trump’s memory serving him wrong. (See Trump’s daily “briefings” for the coronavirus where he typically includes several glaring inaccuracies and outright fabrications per day.)This apparent Trump supporter continues, insisting that we “Gotta get past trump and be critical of hillary on the emails and the foundation.” I can’t do that, I’m just not prone to hypnosis on talking point guidelines, whether induced by Trump or his Breitbart-scripted ads or news media or by the Party that obsequiously accepts Trump’s rhetoric as gospel truth. And when I bash Clinton, it is certainly not about helping Trump, nor hypnotically induced. It’s my own critical thinkolator working, sorry.Regarding the Hillary emails and foundation, the commenter concludes, “Those are problems I will not support and will hold people accountable for regardless of party.” Aside from being way off the topic, this shows a major assumption that the emails and foundation are real problems of executive misbehavior. My view of the emails “scandal” is that it was technologically naïve to think private servers are secure. But like Bernie Sanders’ view, I see the “emails scandal” as just another nit picking distraction from far more important issues the Republicans distract from (similar to the seemingly endless commissions and panels and reports and inquiries into the Bengazi incident, which wasted something like $10 million of taxpayer money and found essentially nothing sinister). Plus, the FBI said she was sloppy but not culpable of any crime. It has no relation to the Petreus case as partisans try to portray since there was no intent to commit a crime as there was in the Petreus case. Regarding the Clinton Foundation I’ll accept what is in Wikipedia because such a high profile issue gets thoroughly edited by friends and foes and ends up a battle of sources and proofs and counter proofs so evidence from all sides can be viewed. Reading that, it’s hard to say there is anything substantially sinister as the National Enquirer and Breitbart claim. In fact, it’s fairly impressive what they’ve accomplished and how it’s been handled despite being such a large operation. (Update: Clinton’s foundation has been exonerated in federal inquiries, as well as the “emails scandal.”) Back to my main points…An important aspect of being in business is that your word is kept. That builds trust among partners. But Trump has alienated even America’s partner nations. The British Parliament even seriously debated whether they should allow Trump to enter the country. That is remarkable because there was no debate in favor of Trump, only whether it was legal and ethical to keep him out. The Queen was gracious to Trump but if you know Royal subtleties you’d know she mocked him in the process.Trump’s estimate of his net worth is around $10 billion, while Forbes estimates it generously at around $3 billion. How could Forbes be so far off? Well, Trump once said that his net worth changes daily, based on how he “feels”. Hmmm. Self-hypnosis? Or what suits his needs?Conclusion: I can’t trust what Trump says to be true. If you can’t trust an executive, it undermines the whole business. The profusion of bluster and bravado he produces hasn’t fooled intelligent people who see right through his carnival barking routine of inducing a hypnosis in his followers of a “feeling” of being “great again” without even spelling out what that really means.UPDATE: As of August 25, 2019 Trump has been President for over 2 years 7 months and has racked up over 12,000 verifiably false public statements recorded by the Washington Post, a truly astounding amount.RED FLAG #3: others CAN be smarter and more knowledgeableTrump is well known to not only not go with the advice of experts, he often would not even listen to them. And apparently it’s a very deeply ingrained habit. He might hire a consultant, but then would brush aside the advice and do what he intended in the first place.So why is that not good? Lots of people go with their gut feeling, right? Yes, and so did George W. Bush when various Middle East experts told him that taking out Saddam Hussein would be worse than leaving him where he was. As terrible a tyrant as Hussein was (killing lots in his own country, suppression of the Kurds, invading Kuwait and waging a war against Iran, etc. etc.), the advice was based on the argument that Hussein actually was a counterbalance to other dangerous forces in the region. Taking him out would upset the balance and lead to all sorts of unpredictable instability that could easily be much worse. That was enough of a reason to not invade. This reasoning was not a secret at the time, it was presented and discussed in the major news media, but the demons of war kept drowning out that voice of reason in Bush’s ear. It’s pretty clear now that it was a horrendous mistake to take out Hussein because it created a power vacuum in Iraq that was filled largely by Iranian influences as well as Al Queda (which wasn't established there before) that morphed into ISIS. The hundreds of thousands killed in the war, the destruction of the Iraqi economy and the aftermath, and the draining of the US Treasury back into a deep deficit added salt to the wound. All because Bush refused to listen to Middle East experts.From Trump we’ve heard what he would do already in the Middle East, just bomb the sh!t out of “them”, and also their families, and torture them “like you wouldn’t believe” because he thinks torture works despite being told even those who ran the torture program now say torture didn’t work, plus it’s illegal according to international law. Leaving aside the questions of legality and immorality is effectively saying the ends justify the means. This was Machiavelli’s approach to ruling. Not an attitude beneficial to the free world.UPDATE: The Iran deal was thrown out by Trump. That deal was arguably better than just letting them go ahead and build nuclear weapons NOW, which they are doing, and then creating yet again another Middle East war that could easily metastasize into a regional or worldwide conflict. That spiked tensions in the regional shipping lanes, and also oil prices.Then there’s the wall thing. If Trump really is so smart and clever and intelligent and the best most brilliant genius he claims he is, then he must be joking about the wall, it must be to just show the world how gullible people are about believing wasting that much money would make any significant difference. It’s utterly ludicrous that Mexico would pay for it. The large majority of illegals came into the country legally and just overstayed their visa. Of course, Trump would know that if he had simply consulted Immigration Services, which I doubt he even bothered, which brings me to the next point.According to some estimates it would be far more costly to the government alone to deport all the illegal aliens, in addition to the major economic damage it would cause, than to just make some kind of sensible workable policy to grant some legal residency status and potential path to citizenship with deportation penalties for screwing up. This simplistic approach of Trump to deport everybody is nonsense, destructive to families, the communities, and the economy, and only creating stress and hysteria on all sides of the debate.UPDATE: Trump’s real agenda is a racism-based immigration prevention policy. Family separation and kids in cages like animals. The USA has lost all moral high ground in the view of the world thanks to Stephen Miller, Trump’s muse on immigration policy.UPDATE: There have been by far more serious scandals and criminal behavior amidst the Trump administration’s appointees than any previous administration. Several have had to “resign” in disgrace. “We’ll get the best people.” It’s looking like the USA has become a banana republic.RED FLAG #4: gotta know what you’re doingTrump has repeatedly shown an abysmal lack of knowledge about how government actually works, how international relations work, how the economy works, what the limits are on the office of the President, what the laws are on many issues, how to cooperate and work with involved people to solve problems, and even how to run a political campaign without tripping over his own words. He just doesn’t (and apparently can’t) educate himself anywhere near what is required to responsibly be the leader of the United States of America.Now it’s true that it’s possible to be the CEO of a company without knowing a whit about how the company’s widgets are made, but you’d have to know or learn something quick about how a business must operate, have some sense of good finance, have some knowledge of the market and the competition, and so forth, just to avoid stupid mistakes. But to be a great CEO, you have to know a LOT about the whole business from the ground floor to the executive offices, about the economic sector it’s in, about human interactions and how to motivate people, and have a distinct and consistent vision of where to take the company to make it prosper. It’s a multi-skill set.Trump’s skill set seems to be limited to how to perpetrate fraud and corruption. The Ukraine “perfect phone call” was the classic example, and even many of the Republican Senators who acquitted Trump did so despite privately holding their noses at the stench of corruption revealed. They acquitted out of shear political motives: fear of Trump retribution — a classic mobster reaction — and fear of Trump voters who don’t know better or don’t care.Update: Trump’s massive bungling of the coronavirus response is another glaring example of his narcissistic personality disorder getting in the way of effective executive decision-making that has played out over months of opportunities to show real leadership, as Governor Andrew Cuomo has shown.The fundamental problem with Trump is that his ability to learn seems to be hampered as evidenced by his incredibly short attention span. His mind is not steady, and as a result he can’t think deeply. It’s not that he doesn’t want to spend time on details to get the big picture, it’s that he literally can’t. You can see this short attention span for yourself in his non-teleprompter speeches. He’s all over the place. And people close to him in his campaign have noticed that Trump tends to talk about the last thing someone said to him, not the conclusion of discussions.Trump’s biographer for The Art of the Deal, Tony Schwartz, who lived with Trump for 18 months so he could gather enough material just to write the darn thing said that he had to just live with the guy to gather that material because Trump couldn’t sit and talk at length or in depth, his attention would go flitting around like a flustered and sometimes angry bird from one thing to the next. In fact he described Trump’s attention span as being “frighteningly short.” (This seems to explain Trump’s favorite way to communicate is Twitter—maximum 140 characters. He reportedly doesn’t even use emails. Too long?)This is extremely alarming. It takes a cool mind and keen steady intellect to absorb all essential information before making good decisions. It takes seriously strong focus to get a clear picture from all the complexity placed on the desk of the President. A channel changing bored fidgety mind is absolutely not the right mind to decide far reaching policies that affect millions.His reading list covers so little territory. MeinKampf, according to his ex. The Bible, allegedly, which is easily doubtful. And Schwartz says Trump did read The Art of the Deal, made a few quips in the margins before it went to press. His attention span there was probably due to it being a book about himself.His Twitter account seems to be a major source. And of course “the internet” and apparently Breitbart News Network in particular considering he hired the head conspiracist there as his campaign manager. Breitbart? I thought it was just another Trump “sarcasm” joke when I first heard that.RED FLAG #:5 “the best” … until it’s “the worst”Trump lives largely in a binary world inside his head. Everything is either “the worst” or “the best”, perfect or terrible, good or bad, hot or cold, left or right, us vs them. There is no nuance, no gradations, no subtleties. Nothing in between. It’s ludicrous hyperbole at best, and a dangerous habit for any president. There are numerous videos of Trump praising people as “great” “the best” and later “the worst” “terrible”. One of them is Hillary Clinton, with Trump specifically praising her from an interview by Wolf Blitzer in Trump’s office in 2007:http://i.a.cnn.net/cnn/2007/images/03/16/trump.blitzer.transcript.31707.pdfBLITZER: Thank you very much. Let's talk politics. All right? A lot of people thinking about politics right now. I'm going to mention some names: give me your thoughts right away. Hillary Clinton.TRUMP: Very talented, very smart. She's a friend of mine, so I'm a little bit prejudiced. She's a very, very capable person and I think she'll probably be the nominee. We'll see, but I think she'll probably be the nominee.BLITZER: Is she ready to be commander-in-chief?TRUMP: I think she is. I think she's a very, very brilliant person, and as a senator in New York, she has done a great job. Everybody loves her. She just won an election with a tremendous majority and she really — she's become very, very popular in New York. And it wasn't easy.BLITZER: Barack Obama.TRUMP: Well, he's a star. I mean, he's really done an amazing job in a very short period of time. The question is experience, and do people want to have somebody get in that doesn't have the great experience? But certainly he's made an impact.Fast forward to 2015 and the only difference is whether the other person is perceived as a political threat or not. But Trump is right about the question of experience, although he doesn’t think it applies to himself.Trump’s biographer Tony Schwartz was “great” until he came out during the convention with his stinging interview in the Atlantic. Then he became “the worst.” http://www.newyorker.com/magazine/2016/07/25/donald-trumps-ghostwriter-tells-allUPDATE: Numerous supporters of Trump, who he praised highly, have since come out publicly saying he’s really bad at the job, ruining the country, and/or needing to be impeached. Typically they are people who have left before saying anything but Justin Amash had to leave the Republican Party because of the heat from his congressional caucus (not his voter base). Paul Ryan. Scaramuchi is the latest.RED FLAG #6 Who’s in charge?He doesn’t seem to really want the job of being president, but if he had anything to do with how to pick the VP, he’s not being straight with the American people about it, which means we’d end up with Mike Pence, Mr. Still In 1994, as the actual president. This was revealed when one of Trump’s sons interviewed a potential VP candidate and the candidate was told he was actually being offered the job of handling all domestic and international affairs. Rightly so, the candidate asked what would Trump do. His son replied, “Make America great again” which is about as nebulous as what’s left after handing off domestic and international affairs. It sounds like Trump isn’t actually interested in the job, he just wants to go do “deals” on a perpetual holiday. What board of directors would put up with this??RED FLAG #7: It’s not supposed to be about “ME ME ME”In my many years I’ve seen some real sociopathic personality disorders but Donald Trump has managed to get Harvard University psychologists to not only publicly say he has this disorder but to even use him as a classic case study in their classes, ticking off every metric on the chart. He has an ego that’s visible from Pluto.Of course, lots of executives have big egos. What is troubling about Donald is he also has exceedingly thin skin (metaphorically). He’s so sensitive about his personal image, especially of being wealthy, that he is deeply prone to distraction by any personal attacks, sending off rants on Twitter when he should be focused on campaign strategy. What if he were to get distracted by loud protests while some unrelated crises were needing urgent full attention as president? It could be a tragic disaster. Or, worse yet, suppose Kim Jong Il taunts Trump? Or Putin? Or ISIS? We could witness a nuclear vendetta all for the sake of his fragile ego. Maybe he’s already realized this weakness and has given the job of response to the important issues to Mike Pence. Maybe he hasn’t.UPDATE: Nope, he hasn’t. Pence may not even make it on the 2020 ticket.National security experts have concluded already that Trump is what is termed “an unwittingly recruited agent” of Putin after seeing their publicly expressed mutual admiration exchange several months ago. Putin is a master of strategy and intrigue, a political chess player having been trained by the KGB, while Trump is still trying to figure out how to win at checkers. It’s no wonder that a long list of Republicans in the national security services have signed a letter saying Trump is a threat to national security.CONCLUSION: I think Trump is a fascinating guy, and in some ways I like him (there is always something good you can find in people), I just think it would be utterly foolish and incredibly dangerous to let him in the Oval Office to be leader of the free world, in charge of activating nuclear codes.UPDATE: Yep, it was foolish and dangerous. Now with all the legal problems mounting against him, he HAS to win the 2020 election or face serious prison time. He’s ruined relations with many of the USA’s best friends, and has coddled several dictators. Constitutional violations galore. He even believe what evangelicals have called him: “God’s chosen one” and “The king of Israel” and other flattering blasphemies because he’s rubber stamping their bible thumping crackpot judge picks (half hour debates in the Senate thanks to Mitch McConnel instead of the 7 days debates).Bet on a cornered rat to survive the election at any cost unless there is impeachment and a Senate conviction first. At this point, there is no conviction among the Senate majority. Constitutional responsibility? What constitution? They would seem to be happy with a dictatorship.Footnotes[1] Joseph McCarthy - Wikipedia[1] Joseph McCarthy - Wikipedia[1] Joseph McCarthy - Wikipedia[1] Joseph McCarthy - Wikipedia[2] Watch CNBC's full interview with Social Capital CEO Chamath Palihapitiya[2] Watch CNBC's full interview with Social Capital CEO Chamath Palihapitiya[2] Watch CNBC's full interview with Social Capital CEO Chamath Palihapitiya[2] Watch CNBC's full interview with Social Capital CEO Chamath Palihapitiya