This is a three part piece. The first, today, looks at the existential threats that Trump faces that could derail him. The second looks at the national polling, at the third party challengers, and how parties have been performing in real elections. And the final piece looks at the swing states and what is happening on the ground.

At the end of which, I will, probably, opine on what Trump’s chances are of becoming the first returning President since Grover Cleveland.

Let’s get this out the way. I don’t think that Trump will be convicted of a criminal offence, and be sent to jail, before November’s election.

My gut is that only the false accounting trial happens. And while he will likely be found guilty, it is almost impossible for him to be jailed for this. And this prosecution is by far the weakest of those that he is facing. It looks like what it is: politically motivated. (Of course, when Attorney Generals are beholden to their voters, and their voters hate a particular politician, then you’re going to have this issue. Maybe, America, you might want to think about whether this really should be an elected role.)

Will this trial be a negative or a positive for Trump?

Both.

It will be a negative because it means he won’t be off campaigning, and it’s always possible he will have a meltdown in Court. It’s a positive because it will help motivate his base, especially given how minor the infraction is.

But more important is… the Civil Cases

There are two civil cases of note, and they’re important (mostly) because of money.

Let’s start with the Carroll case. It’s often forgotten why the Carroll case exists. It does not exist due to Ms Carroll suing Donald Trump for assaulting (or raping her) 30-odd years ago.

It exists because Donald Trump repeatedly defamed Ms Carroll at rallies.

He found he got a big cheer when he derided her in front of his supporters… and he couldn’t help himself… he did it time and time again. And then she sued him for that defamation, and he lost the trial. And then he did it again.

And now he’s on the hook for $90m.

And you know what, on appeal, that will no doubt be cut back. But if he can’t stop defaming her in speeches, then there’ll be another trial. And another award.

But that’s far from his biggest financial concern. Much more serious is the $450m related to the Trump Organization’s… aggressive… property valuations (one number for the banks… another much lower for the government).

Now, there are some (including me) who would say there’s always wriggle room: if you report a property as worth $10m to the government and $11m to the bank… and you show your workings in both cases, and both are “in the round”, then that’s one thing. It’s something else when there is a 2x delta. Or, as there seems to have been in this case, a 10x one.

On this Trump has been lucky. There are plenty of property developers who deliberately understated the value of properties, and who ended up facing criminal charges. This guy built apartment complexes and underreported the value of properties to save about $2.5m in taxes. He went to prison for 15 months.

The civil judgement ($454m) is being appealed, but Trump’s problems are compounded by the fact that the Trump Organization’s former CFO, Allen Weisselberg just pled guilty to perjury. And he’s off to prison for five months.

Now, Mr Trump is a rich man. But he is likely also a highly leveraged one. There are plenty of property developers who were rich when interest rates were 3%, only to be bust when they were 6%.

Simply: refinancing debt when interest rates are up is not really where you want to be. If you have a property valued at $100m with $50m of debt at 3% , you really don’t want to refinance to $75m of debt at 6%.

I suspect that Mr Trump will manage to sell off a property or two, and refinance a few, to pull through. But he doesn’t have $550m in cash on hand, and there is a non-negligible risk that he will miss an interest payment. And if he does, then he will likely breach the covenants on all his debt, resulting in bankers pulling loans… That would be very serious. Of course, Trump has the option of going abroad (further abroad that is, most US banks stopped lending to Trump a long time ago, and he’s been dependent on Deutsche Bank). I have no doubt that the Russian government would love to “help” him out of financial troubles… But that’s not without (electoral and legal) risks too.

A financial meltdown is not a 20% risk to Trump’s reelection chances: but it does exist. There’s a small (3-7%) chance of “something bad” happening that would imperil his reelection chances.

Plus – of course – these trials are going to be very stressful for Mr Trump.

He’s a month younger than OGH, but he’s overweight, has a terrible diet and doesn’t exercise much. If you combine that with a lot of stress, then there is a not insubstantial chance of a medical issue. Not death, necessarily, but we can’t rule out a stroke, an embolism, a heart attack, or a cancer diagnosis. Or a million other possibilities whose likelihood increases exponentially as one gets into one’s late 70s. There’s only eight months to the election – of course – but given the stress he’s under, the chances of a medical event have to be at least 5%, and possibly nearer to 10%.

Health and financial issues, not a jail cell, are the biggest existential threat to Trump making it to November unscathed.

Robert Smithson