How Trump Wins by Losing

8 min readDec 13, 2020

Trump knows he didn’t win the election. He also knows that an even bigger loss is looming. He knew long before the election, that his business, and the Trump brand, has some reckoning in the coming years. When it comes to his brand, his family name, he will stop at nothing to protect and preserve it. All of the latest post-election shenanigans, hype about election fraud and irregular ballots has less to do with actually overturning the election and more to do with keeping people thinking he can overturn the election — and keep collecting those donor dollars.

If you think about it, he is not doing anything different after the election than he had been doing before the election. Trump is doing what Trump does best. Promote the brand, his brand. Ask him: He’ll tell you that he’s the best promoter of business. He’ll remind you that as far as promoting one’s brand, he’s “done more for business branding than any other promoter, except for maybe P.T. Barnum.”

He doesn’t care that he won’t be President. Don’t forget, he never expected to win in 2016 — he was completely unprepared to govern — and it showed. He enjoyed the perks: The House, the security, the attention, oh, that attention! Media from around the world tripping over every word that he spoke and every character that he tweeted. It’s a narcissist’s fantasy, and Trump was living it. So, for him, being the President was about fulfilling that need. Now he needs to find a way to get that level of fix, but actually being President, he could not care less.

But it’s not just all fun and games. It’s not simply how many followers he has on Twitter or how large an arena audience he can get. He needs money. Real money. No question, he is a billionaire’s billionaire. His wealth is real. He is not broke. However, his wealth is in assets, real property almost exclusively. Many of which are held as collateral for loans. Some of which come due very soon after he leaves office.

So, consider this: Donald Trump realizes he has lost the election, and knows that he has loans due without the cash reserve to pay back those loans, and if he were required to sell off the property, that would diminish his brand, lessen his stature. We’ve just established how important his brand is to him. So, instead, he finds a way to fundraise…and it’s not his first rodeo. Recall the Trump Foundation, a supposedly non-profit foundation that was shut down by the courts of the State of New York and its money rightly distributed to charities — after finding massive irregularities and potentially illegal use of funds, all of which were donated. A history of using other people’s money to meet the needs of his bottom line? That’s right America.

The money being donated and contributed to the legal fight against the fraudulent election, to support unsubstantiated claims of voter fraud and election irregularities, is his money. He will do what he wants with it. Yes, some of it is being spent on the half-hearted legal challenges being submitted to and tossed from the courts, but there has been little real effort to mount a sustained challenge, because it is expensive! That would mean less money left over to pay off the loans coming due in 2021 and 2022 to the tune of about $450,000,000…too many zeros? That’s 450 million dollars. With about the same amount due again over the subsequent 2023–2024 years.

He’s known for a long time when these loans would come due, and if he had not become President, we might have had to endure another couple of seasons of Celebrity Apprentice to generate the necessary revenue. All things considered, I would have opted for that, but I digress.

He knew he needed cash for 2021 and beyond. Is it any surprise that he began stoking the fire around the need to fight a fraudulent election, that the electoral system is corrupt, and that he would fight the system should he lose. He was setting the scene for post-election fundraising under the guise of having to fight the system. It worked. His pockets are lined with cash now, having raised huge sums of money since Election Day, some estimates put it close to one-quarter of a billion dollars… and the election is long over! Even with court fees for the feeble challenges against claims of voter fraud, he will have amassed enough money to cover the loans due in 2021, and the donations keep coming.

Even if he can’t legally spend money raised through the party on himself, he will have undoubtedly collected “a lot” (say it witht he Trump accent for best effect) of private donations along the way, which he can use at his discretion. Then again, legal constraints don’t seem to be a strong deterrent for Trump and his bandits. In any case, it’s a federal crime, and if so committed he will just pardon himself before he leaves, and let the courts — ultimately the same Supreme Court that he tipped in his favor — fight it out for months, perhaps years to settle the issue on whether a President can pardon oneself.

From the perspective of the common citizen, crowd-funding from his base, who he has deliberately enraptured with lies and misinformation, is about as low as it gets. The same people who likely need the money the most, are the ones willingly giving it over to him — like a tithe to the evangelist — hoping for some salvation.

From the perspective of Trump, it’s too good to be true. To the point that Trump will continue to stoke the fires against the established systems of government for a long time after he leaves office. It’s too lucrative not to do so. As for any plans to run again in 2024… I predict that there is no way he will run. He wouldn’t risk the chance that he might win. He doesn’t want to be President. However, he will conintue to let his followers believe that he will run, and meanwhile keep collecting those donations.

How Trump Wins by Losing

Written by Kixot