Was losing the election baked into Trump's plan all along?

If you look back on Trump’s rap sheet, his most effective schemes have had an element of failure built into them on some level.
Image: Donald Trump walks against a red back with white text that reads: MAKE AMERICA GREAT AGAIN AGAIN!
The entire Trump presidency has been an exercise in brand management gone awry.Anjali Nair / MSNBC; Getty Images

This weekend was the collective mental equivalent of a deep, drawn out exhale as it became clear that President Donald Trump had come up short in his quest for a second term. Already the deep dives into how he became the first one-term president since 1992 are piling up, as we begin to look forward to a day when he’s no longer taking up space in our brains.

Typically for Trump’s M.O. and general personality, the appearance of things matters more than the underlying facts.

Because, let’s be honest, it was a lot of effort to keep one eye on his various improprieties, from the buffoonish and simple personal failings to the cruel and callous official acts. Trump is almost cartoonish in his villainy. His lies and plots — a list is almost impossible to fully catalogue — are embarrassingly transparent at times.

If you look back on Trump’s rap sheet, his most effective schemes have had an element of failure built into the plan. Sometimes these failures have, in fact, been the preferred outcome. And as he continues to rail against President-Elect Joe Biden’s victory, it’s not lost on me that his current strategy doesn’t require him to ever actually walk away as a winner.

It’s an art that he’s spent his entire adult life perfecting. The New York Times, in a Herculean bit of reporting, pieced together several of Trump’s various machinations of enriching himself. The first, and most damning, tracked how he maintained the illusion of a mighty empire on the surface, allowing him to continue to borrow prodigious amounts of money and grow his real estate empire. Under the hood, his federal taxes showed him losing vast amounts of money every year, both through actual losses and potentially creative bookkeeping that seems designed to reap millions of dollars in tax write-offs. His own failure is cooked into the ploy, harnessed to increase his wealth. This con serves as an archetype for most of his other schemes, where he poises himself to benefit as much as possible from failures.

By that same dint, the entire Trump presidency has reportedly been an exercise in brand management gone awry, a rare case where Trump outperformed his own limitations. By several accounts, he wasn’t prepared for actually succeeding in his longshot run when he launched it in 2015. His eventual loss, he and other campaign staffers believed, would leave him free to ride the momentum into a new wave of business opportunities, according to Michael Wolff in his book “Fire and Fury: Inside The Trump White House.”

Four years later, Trump has gotten used to the idea of being in charge of the country, even as he’s never really understood what that entails.

Typically for Trump’s M.O. and general personality, the appearance of things matters more than the underlying facts when he’s busy shaping the narrative around himself. Trump wanted to look like a good potential president, absorb the adulation of the people he realized would cheer when he said things like “Drain the Swamp,” and then bounce back to Mar-a-Lago to enjoy it all. As for his famously fragile ego, he had that covered, too.

“This is bigger than I ever dreamed of,” Wolff says Trump told the late Fox News founder Roger Ailes a week before the election, “I don’t think about losing, because it isn’t losing. We’ve totally won.”

The plan, of course, backfired when it worked too well. The thunderbolt of winning reportedly initially frightened Trump, but that faded as he settled into the trappings of the office. Four years later, Trump has gotten used to the idea of being in charge of the country, even as he’s never really understood what that entails. And so he’s attempted to do whatever he can to make sure he can stay in power, especially with the threat of criminal charges looming should he become a civilian again.

Twice in his re-election bid, technically launched soon after he took office, Trump attempted to put his finger on the electoral scale. In the first, the plot that ended up prompting the House of Representatives to impeach him, there was the top-level scheme — getting Joe Biden’s son, Hunter, prosecuted in Ukraine, which was never guaranteed success — and then the underlying goal, damaging Joe Biden politically, which didn’t require it.

It didn’t matter if Ukrainian president Volodymyr Zelensky never actually ordered his prosecutor-general to file charges against the natural gas company where Hunter Biden worked, or against Joe or Hunter Biden themselves, let alone actually convict them. Trump didn’t even need an actual investigation into the Biden family — it wasn’t necessary.

No, Trump extorted Ukraine, illegally holding back $250 million worth of military aid, because he knew the announcement of an investigation was the important part. That’s what gets headlines, makes chyrons, sticks in peoples’ heads. That’s what he could use to bludgeon Biden with throughout 2020. It would be no failure if the case simply vanished a few weeks after it was announced — anything after that point would have been a welcome bonus.

If he hadn’t gotten caught, thanks to a whistleblower’s account of his suspicions to Congress, it may have even worked — Zelensky was reportedly days away from making the claim in a CNN interview when the whole thing was exposed. “Ukrainian president announces corruption investigation targeting Joe Biden’s son” is a headline that few news outlets would have blinked at initially running without evidence of Trump’s hand in it. By the time the reporting showing it was all a con had been done, it’d be too late.

The second of his attempts to sway the election has lacked the subtlety of the first. It’s been obvious for months that Trump’s attacks on mail-in ballots — falsely claiming that they were rife with fraud — were aimed at discrediting them ahead of the election, when they were likely to favor Biden. It’s a theme he’s kept up since election night, tweeting several times that he’d won the election and going on a rambling rant at the White House press room’s podium on Thursday evening.

Thankfully for the floundering legal effort that’s been slapped together to prove that point in court, the Trump campaign doesn’t need to win the cases being filed — not yet. He doesn’t even need the states to confirm him the winner. Trump just needs to stall, and he needs to tell his supporters that his many enemies are working against him yet again.

If Trump’s been obvious, his advisers have been downright transparent about the end goal: getting the Supreme Court to toss out hundreds of thousands of legitimate votes in Pennsylvania and elsewhere. Press Secretary Kayleigh McEnaney said it on Fox News on the night of Nov. 4, when asked whether ballots put into the mailbox and postmarked on Election Day that arrive by Nov. 6 should be tossed: “No, we believe every vote on Election Day should be counted. But it’s those that arrive after the Election Day that we are fighting.”

Harmeet Dhillon, co-chair of the new group Lawyers for Trump, said it on Lou Dobbs’ Fox Business show on Thursday night: “Meanwhile, we’re waiting for the United States Supreme Court, of which the president has nominated three justices, to step in and do something. And hopefully Amy Coney Barrett will come through and pick it up.”

His campaign reportedly asked pro-Trump voters in Pennsylvania to send in their absentee ballots after the deadline, in an effort to boost his lagging prospects there and offer the votes up as proof of the voter fraud it has claimed without evidence has occurred there. But even with a 2 -1 conservative to liberal balance on the Supreme Court, there’s not much promise that a case will come before them that gets a majority of the justices to throw the election his way. Which is why it’s almost more important for Trump to sell the idea that he’s been the real victim here to his supporters.

They need to believe that the only way he could lose is via betrayal, trickery from the Deep State, or a Democratic plot against him. With the support of outside groups coordinated by Trump allies, that lie is taking root and drawing out protesters as seen in Michigan and Arizona. It’s a lie that’s been embraced by Trump’s top political allies — like Ohio’s Rep. Jim Jordan, House Minority Leader Kevin McCarthy, former Speaker of the House Newt Gingrich, Senator Lindsey Graham, and Republican National Committee chair Ronna McDaniel. All of them have continued to push the election fraud claims, even as privately his top legal minds agreed as early as Friday that there were no legal routes that could swing the election.

That hasn’t stopped the campaign from fundraising for this boondoggle of a court battle — the fine print of their appeals showed that at least half of the money raised will go toward retiring the campaign debts of a supposed billionaire, one who’s managed to avoid paying any of his own money during this race. In fact, he’s netted at least $2.5 million directly from American taxpayers during his time in office. Not a bad bit of grift.

As of right now, there are two outcomes that can result from this current gambit, absent a Supreme Court intervention. In one scenario, his supporters rally around him and through a combination of bullying, protests, and violence keep things chaotic in the hopes of being sworn-in as president again come January, as Barton Gelman described in his chilling piece for The Atlantic.

Or things never quite break Trump’s way, the courts decide to let the votes stand, Biden becomes the 46th president. Trump never really concedes and, should he avoid prosecution, he gets to become a kingmaker in the Republican party, with a role in vetting his potential successor in 2024. Maybe he launches the Trump-branded media outlet that Jared Kushner has reportedly been shopping around. Or he could go the Grover Cleveland route and run again himself, aiming for two non-consecutive terms. Either way, a power unlike anything he had before occupying the White House would be his, unmarred by the responsibility that comes with actually being president.

New York Magazine’s Olivia Nuzzi reported that the latter was at this point a preference for Trump, according to a friend of the president:

“A lot of what Trump says is the opposite of what he means. That’s true of all of us, to some extent,” the president’s friend said. But when Trump said he didn’t mind losing to Biden, even though he famously hates losers of any ilk, his friend believed him. “He doesn’t believe losing is shameful — quitting is bad. Losing isn’t,” this person said.

As of Sunday night, Trump has yet to even offer the idea that such a thing has occurred let alone a concession. In fact, during his appearance on Thursday night, the president never actually said the word “loss” or any variation thereof about the election. Which, given his approach in 2016, makes sense. Why label yourself a loser when, as he said then, “it isn’t losing. We’ve totally won.”