What Kind of Desperado Is Donald Trump?

My mother was a very practical woman.

Not in a joyless way, mind you. She appreciated beauty for its own sake and saw the world as something lovely, and wished to adorn it. As I write, I sit under one of her paintings. 

Like everything in her, my mother’s abundant love for her people was not abstract. It took on material form in the beauty and comfort she created for her family, and most of all wanted to enjoy it together with us.

She was no hard-nosed pragmatist, but she had little time for the theoretical. It would be her lot, though, that her youngest of five children would be exactly the opposite. She was a person who asked “what,” but I was born asking “what if.” 

And very high on her list of uninteresting abstractions was history. And so, it had to be that it was my fascination. As a boy, I could always get my father to talk with me about history—the world, America, our town, our family, anything. Never my mom, though. Joan Stirewalt lived in the now.

But in my surely dreadful efforts to wheedle out of my mother an opportunity to natter on about what I knew and what I wondered, there was one topic to which I could always resort. And of all things, it was the story of murderous bank robber John Dillinger.

Dillinger was gunned down by FBI agents outside the Biograph Theater on Chicago’s North Side in 1934, the year before my mother was born. But something in the story of that Depression-era desperado captured her imagination. 

They both grew up in Indiana, so maybe that was part of it. She had been raised at a time and in a place where his legend and celebrity would have been hard to escape. But in the dozens of times I nudged her into talking about Dillinger, she would always remark on how handsome he was.

“Women were drawn to him like moths to a flame,” she would tell me. And, I’ll admit, that as bank robbers go, Dillinger was pretty. So maybe that was enough: A woman who loved beauty was fascinated by a beautiful person who was capable of hideous things. 

But there was another refrain, too. She talked about how people admired him. How the people of the Midwest in that hard-bitten era appreciated that he was robbing the same banks that had foreclosed on so many homes. And indeed, Dillinger and his gang made quite a show of destroying the mortgage certificates they found in the bank vaults they plundered.

“They thought he was like Robin Hood,” my mother would say.

A beautiful bandit who took from the rich and gave to the poor. Pretty good for folklore. But best of all for Dillinger’s legend, he had the decency to not just die young, but to be killed in spectacular fashion. No wonder he captured the imagination of a little girl in Indianapolis.

America has long loved its bad men, some badder than others. Some were real heroes, like the privateers who harassed enemy shipping during the Revolution and the War of 1812. Some were just thugs with good public relations, like Al Capone. And some were mostly works of fiction, like Billy the Kid.

So what’s Donald Trump?

I’ve thought often of my mother’s soft spot for Dillinger as I watched Republicans close ranks around Trump. These are mostly people who wouldn’t tolerate Trump’s conduct in an employee or neighbor. They would be deeply ashamed if a member of their own family was on trial for hiding hush money payments to a pornographic performer or was caught lying about stolen documents—to say nothing of his efforts to steal a second term in office.  Yet with Trump they have found a way not just to excuse the bad behavior, but to turn it into a mark of honor.

It is only because he’s such a threat to the bad people in power, the reasoning goes, that he is being picked on in this way. And while he is not beautiful, he is vivid and spectacular; a larger than life celebrity. He even leans into the comparison with Capone, the high-living, dapper don whom the Feds had to bust for tax evasion because they couldn’t get him for bootlegging and racketeering.

This helps us understand how the charges against Trump helped him solidify his grip on the GOP. Republican voters saw Trump as being punished not for his misdeeds, crimes for which they believed Democrats had not faced consequences, but for being one of their own. A martyr for their cause. 

We can’t know whether an unindicted Trump would have still won a third Republican nomination, but we can be very certain that the charges made his task far easier. The GOP primaries weren’t a choice between different Republican candidates but whether voters who had been backing Trump for eight years would abandon him when President Joe Biden and the Democratic machine were trying to lock him up.

But now we find Trump, nomination in his pocket, in court. And it’s not a spectacle. It’s not on camera. It’s a grubby case in a grubby-looking courthouse. Indeed, the outcry from Republicans that this is a penny-ante bookkeeping case reinforces the grubbiness. Whatever one thinks of the merit of the charges, this is not the big time. It feels and looks small. And the tawdriness of the details and scumminess of Trump’s past associates—the sex worker, the tabloid publisher, the shady bagman who was his lawyer—add to the smallness.

Six weeks is a very long time in a presidential election cycle. Six weeks ago, we were talking about the State of the Union address and the Robert Hur report. Both are now specks in the rearview mirror. But six weeks from now, the world may still be waiting on a verdict from the Trump trial.

I don’t expect that any of that will shake the core support that Trump has from Republicans. Partisanship will not allow many, if any, to reconsider their choice of a nominee. 

But what I do expect is that the very unglamorous, very small affair that is playing out in Manhattan will diminish Trump’s image. 

If he beats the rap with an acquittal or even a hung jury or some other mistrial, I expect it will help him significantly in the campaign. They tried to take him down, he will say, but they couldn’t do it, like King Kong swatting away the airplanes. 

But if he’s convicted? The good gangster stories don’t end up in appeals courts and sentencing recommendations. That’s not the stuff of legends. That’s just a grind.