Opinion by Jill Filipovic
(CNN) — Will former President Donald Trump accept a plea deal, potentially sparing himself prison and sparing us all a repeat of his presidency?
That’s the question being posed by New York University professor Scott Galloway in a now-viral email newsletter. Trump, Galloway argues, can certainly do the math on his prospects: Trump is facing federal charges in two jurisdictions, along with state charges in a third and the possibility of state charges in a fourth (he has pleaded not guilty to all charges against him). In a country where federal prosecutors overwhelmingly win their cases, Trump’s odds of going to trial and winning both federal cases are slim — and he may face similarly daunting odds in the other cases. Even Trump, Galloway argues, can do math that simple — and thus would want to look for a deal to avoid a possible prison term.
It’s a compelling argument, and one that would certainly be better for the nation than Trump winning in 2024 and pardoning himself; it would be better for Trump than winding up behind bars. Any reasonable person would look at the weight of the cases against him and the long odds of prevailing in all of them, and start talking about his options.
The problem is that Donald Trump is not reasonable.
Trump has been embroiled in thousands of lawsuits; he’s the first former president to face federal charges. He is, to put it gently, unique among American leaders.
Despite the many claims against him and his companies, though, he has seen vanishingly few personal consequences. While — contrary to his own claims — he often settles cases, the penalties paid don’t make much of a dent in his lifestyle of golf clubs and private jets. When he loses, even fair and square like he did in the 2020 election, his refrains include it’s not my fault, it benefitted me and it didn’t happen.
And this has indeed benefitted him: He has remained spectacularly wealthy despite his companies declaring bankruptcy multiple times, clearing his debts without losing his lifestyle. Despite being a liability to his own party and engaging in dangerous, democracy-undermining conspiracy-theorizing, he remains the Republican frontrunner for the 2024 presidential nomination and putative party head.
He has also seen just how quickly his former opponents will come around if they think they’ll benefit, too. The list of conservative politicians and talking heads who warned of Trump’s dangerous ideas and deranged temperament during the 2016 campaign, only to turn around the kiss the ring as soon as it was clear he was winning, is depressingly long.
One has to imagine that the former president has learned a few lessons in his day: that he is personally above the law, that he can bend people around him to his will, that the usual maxim that “actions have consequences” doesn’t apply to him and that he can behave with impunity.
The calculus Trump is making with these indictments isn’t just about his chances of conviction. It’s also about his chances of winning the presidency in 2024. Anyone who believes that President Joe Biden will handily triumph in 2024 should think back to Trump’s surprise upset in 2016 — Trump, no doubt, is. Some polls show the two in a dead heat, even after news of these indictments.
If he’s reasonably confident that he can win in 2024, then Trump could claim he has little to worry about, as his plan is no doubt to pardon himself. That’s an extra bit of motivation — aside from his general desire for power, influence and acclaim — to keep himself focused on winning the White House. This may also stir up his supporters, many of whom seem at least partly motivated by a desire to stick it to liberals and other perceived enemies: What better way to make a mockery of rule-of-law moderates and democracy-obsessed libs than to get their guy back into an office vested with the power to put himself and his associates outside the reach of the law?
Betting on a 2024 win is a big gamble for Trump, especially if the consequence of that loss isn’t just humiliation, but a jail cell. But even if Trump loses, he appointed three judges to a now far-right Supreme Court, as well as dozens of others to the federal bench. He may even be factoring in Biden’s impulse toward moderation and bipartisan cooperation, and hoping the president will pardon him in a step toward healing a badly fractured nation.
There is also the question of whether prosecutors would even offer a deal Trump might consider. On the one hand, a deal that barred Trump from running for public office would neutralize his ability to impose his will from the White House. On the other, it might only confirm exactly what Trump has long argued: that he is a victim of so-called elites hell-bent on keeping him out of office and blocking the desires of real Americans.
Unless a deal also barred Trump from so much as speaking about US politics — which seems highly unlikely — it’s hard to imagine how Trump wouldn’t simply use pleading out to avoid the humiliation of an election loss while continuing to feed dangerous lies to his supporters and undermine the public’s faith in the electoral process.
Trump’s defense team is no doubt looking for a way to keep their client out of prison. But Trump’s calculation is likely more complicated, colored by his ambitions, his personal history and his belief in his own power to make things go his way. One thing is clear: Predicting with any amount of certainty how Trump will behave is a losing game.
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