Will Donald Trump go to prison?

Donald Trump faces four criminal indictments in four separate jurisdictions.

Nearly 100 felony criminal charges have been levelled against the former president, who remains the presumptive nominee to be the Republican Party’s presidential candidate once more in 2024.

As his legal battles grow more complex by the day, a serious question has emerged: what happens if Mr Trump wins the nomination and campaigns for the general election as a convicted criminal?

That possibility, in turn, raises another simpler question: could the 45th president of the United States go to prison?

Between his 88 felony counts (three were recently rescinded in Georgia), Mr Trump faces a total of roughly seven centuries in total jail time, spread between dozens of various charges of differing seriousness.

Obviously, the luxury real estate mogul is not going to be sealed inside a federal penitentiary for all of eternity but the increasingly wide range of actions for which he is now being prosecuted is slowly chipping away at the likelihood that he will evade the inside of a prison cell forever.

Much will depend on the US Supreme Court’s ruling on Mr Trump’s speculative presidential immunity defence, arguing that he should be completely shielded from criminal prosecution over any action he carried out while in the White House, which the highest court in the land heard oral arguments about on 25 April.

Here, we take a look at the four prosecutions Mr Trump currently faces and how each affects his chances of campaigning behind bars this year.

1. The New York ‘hush money’ case – maximum of 136 years

The first indictment to drop against the former president deals with conduct committed the longest ago.

Mr Trump was accused by Manhattan district attorney Alvin Bragg last April of 34 counts of falsifying business records in the first degree, a felony under New York state law, to conceal “hush money” payments allegedly made on his behalf to porn star Stormy Daniels and ex-Playboy model Karen McDougal in 2016 to secure their silence about sexual affairs he is accused of having with both women a decade earlier. Each count carries a maximum sentence of four years in prison.

However, such sentences are only doled out with mitigating circumstances, like previous felony convictions or based on the seriousness of the crime.

The accusation against Mr Trump is largely victimless and as such a judge is not likely to sentence him to anything more than fines or, at the most, probation and community service, were he to be convicted by a jury.

The trial for the case began on 15 April in New York and, on 6 May, the presiding Judge Juan Merchan found the defendant in contempt of court for a tenth time, having already fined him $9,000 for nine breaches of a gag order imposed on him, and explicitly warned Mr Trump that any further violations would force him to consider jail time.

The judge said the maximum penalty of $1,000 per offence was clearly no deterrent and that the former president was leaving him with no choice as his criticism of the trial constituted “a direct attack on the rule of law”.

Donald Trump is escorted into court for his arraignment in New York in April 2023 (AP)

2. The Florida classified documents case – maximum of 450 years

This case first exploded into the public eye when the FBI raided Mr Trump’s Mar-a-Lago home in Palm Beach, Florida, in August 2022 in search of boxes of classified documents he should have handed over to the National Archives after completing his term in the Oval Office in January 2021.

The episode resulted in allegations that have attracted serious criticism from the Republican’s former deputies, including his own US attorney general Bill Barr, with Mr Trump accused of mishandling sensitive information pertaining to national security in an egregious manner by Justice Department special counsel Jack Smith, including, in one instance, supposedly showing off top secret intelligence to guests at his golf resort in Bedminster, New Jersey.

He is also accused of obstructing justice and making false statements about the withheld files.

All in all, the ex-president faces a maximum of 10 years in prison per count of willfully retaining secrets and 20 years per count of obstructing justice. While the latter offence comes with a higher maximum sentence, it is the former about which Mr Trump should be more worried.

Convictions of wilful and/or reckless retention of classified information frequently result in prison sentences of several years or more. Mr Trump faces more than 30 of those charges.

The trial in this case was provisionally set for 20 May, although Judge Aileen Cannon continues to raise eyebrows with her drawn-out pretrial hearings and occasionally baffling orders about the case.

Prosecutors have requested that the trial start on 8 July while the defence team have requested 12 August.

Donald Trump appears alongside his aide and co-defendant Walt Nauta and attorneys Chris Kise and Todd Blanche in Miami, Florida, in June 2023 (Reuters)

3. The DC federal elections case maximum of 55 years

The Justice Department’s second indictment charges Mr Trump with crimes related to the 2020 presidential election and the months-long effort by his team to overturn the result in his favour.

Two basic parts to this case should concern the ex-president: the possibility that he will be convicted of conspiracy to defraud the United States and conspiring against Americans’ right to vote in free elections and the possibility that he will be convicted of directly attempting to block the certification of the election results by summoning a mob to attack the US Capitol on 6 January 2021.

The former is almost assuredly less of an uphill battle for prosecutors, given how much evidence is now public regarding the Trump campaign’s election manipulation efforts. The real battle in this regard will be for prosecutors to prove that those efforts went beyond acceptable legal limits.

The latter is somewhat harder to prove. Mr Trump and his allies have fiercely denied ever since the attack on the Capitol first took place that the pro-Trump mob that left lawmakers hiding in fear for their lives was directed by the president himself.

Mr Trump will likely point to his (belated) video message that day urging the rioters to go home as evidence that this was not the case.

Should he be convicted on either point, however, he faces steep maximum prison sentences for each count, in particular the obstruction of proceeding charges, which carry 20-year maximum terms.

The trial, in this case, was provisionally set for 4 March before that was scrubbed due to delays in resolving the immunity issue, with presiding judge Tanya Chutkan saying she would reschedule it “if and when” the matter is definitively settled, leaving the case in a temporary state of limbo until the Supreme Court weighs in.

Donald Trump claimed he witnessed ‘filth’ and ’decay’ in Washington, DC, after his arraignment in early August 2023 (Getty)

4. The Georgia racketeering case maximum of 76.5 years

The final indictment to drop was the case brought against Mr Trump by Fani Willis, district attorney of Fulton County, Georgia, and is unique in that it also involves the only charges to carry minimum prison terms.

While Mr Trump is also accused of a host of minor to moderately serious felonies in the state, it is his charge of violating Georgia’s RICO (Racketeer Influenced and Corrupt Organisations) statute that should have him the most concerned. It carries a minimum prison term of five years, with a maximum of 20 behind bars.

A RICO charge will undoubtedly be the hardest for Ms Willis and her team to prove, as it involves fewer allegations (and less evidence) of specific illegality and instead relies on the prosecution convincing a judge and jury that the overall effort by Mr Trump to change the election results in Georgia crossed the boundary into becoming a fully-fledged criminal enterprise.

Should that fail, however, Mr Trump also faces 12 other felony counts, all of which carry the potential for incarceration.

Donald Trump appears in a police booking mugshot released by the Fulton County Sheriff’s Office in Georgia in August 2023 (Reuters)

How likely is a Trump jail term?

It is hard to say, but one thing is clear: while the situation ultimately looks black for Mr Trump, his strategy of “delay, delay, delay” appears to be bearing fruit as his court dates are routinely pushed further and further back to accommodate motions volunteered by his attorneys.

Legal experts who have looked at the Justice Department’s prosecution related to the election challenges have almost uniformly remarked on the strength of its case and the efforts made by the agency to narrow down the case to a point where it can proceed through the courts before the general election takes place on 5 November.

The question also lingers as to how long Mr Trump can maintain his costly legal defences in all four cases, given how many millions of dollars four high-profile criminal defence trials are likely to add up to. A recent report found that he was burning through cash at an unsustainable rate of $230,000 a day.

In the end, the answer to the question of whether Mr Trump will ever see the inside of a jail cell may come down to not whether he will be convicted, but whether jailing a former president is even feasible.

Should he win the general election this year, an entirely new layer of complexity is added to the mix.

The one certainty surrounding the multiple prosecutions is this: Donald Trump, regardless of the outcome of his many trials, has already pushed American democracy far into the bounds of the unknown and the unprecedented.

Whatever happens from here is an example of the world’s most powerful democracy making it up as it goes along.

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