Trump's legal woes are clashing with his political ambitions

Former US president Donald Trump speaks during a rally in Iowa. AP

Former US president Donald Trump still looms large enough that two national US calendars, which in the past have always run in parallel, seem set to collide as his gravitational pull slams them together. He faces a mounting set of legal and criminal reckonings and it's almost impossible that all will be postponed. Many are set to intersect with the schedule of political primaries, party conventions and even the next presidential election.

Since Mr Trump faced his first criminal indictment in Manhattan in March on campaign finance and business records and tax falsification charges, he has appeared subdued and chastened in the dock. Unlike the civil defamation lawsuit, based on a sexual assault that a jury determined he indeed committed against writer E Jean Carroll, he won't have the option of not attending these criminal trials.

Last week, a Trump-appointed Federal District Judge in southern Florida, Aileen Cannon, rebuffed his request for an indefinite postponement of his trial on 37 felony counts related to the alleged purloining, mishandling, concealing and unauthorised exposure of numerous highly sensitive government documents. Instead, she scheduled the trial for May 20, 2024.

Supporters of former US President Donald Trump at a Save America Rally on June 25, 2022, in Illinois. Getty

While many complications may create delays, including the difficulty of getting attorneys cleared to review classified materials and finding a qualified jury, the Southern District of Florida is noted for its “rocket docket”, and may prove unsympathetic to his favourite legal tactic of endless delays.

In the last quarter of fundraising, most of Mr Trump's donation dollars went not to his presidential campaign, but into paying his mounting legal bills

Meanwhile, a judge in New York City has scheduled March 25 for Mr Trump's state-level charges. As with the federal-level Florida case, he will be required to attend, while presumably his Republican rivals will be campaigning, fund-raising and debating.

By then the former president will already be embroiled in a second civil lawsuit brought by Ms Carroll on the same essential facts because he inexplicably repeated his accusations that she was lying about their alleged encounter after she won a resounding jury verdict last year. Shortly after, Mr Trump took to CNN to repeat his denials, claims that he didn't know who she is (despite numerous photographs showing them together), and implications that she is unbalanced.

A civil jury found that Donald Trump sexually assaulted the writer E Jean Carroll, pictured centre, in the 1990s. AP Photo

Interest in round two, which will surely result in yet another judgment against him, has been stoked by a stunning recent ruling by federal District Court Judge Lewis Kaplan. It held that, while the civil court jury ruled in favour of Ms Carroll on sexual assault and not rape charges under the exact meaning of the terms under New York State law, nonetheless their findings of fact establish that Mr Trump had indeed “raped” her “as many people commonly understand the word ‘rape’” .

It will not help Mr Trump in any elections whatsoever, even Republican primaries, that a federal judge has ruled it is legally accurate to describe him as an established rapist under the commonly understood meaning of the term. All of that is likely to be reinforced and disseminated by a disastrous second lawsuit he could have avoided by simply restraining his impulse to lash out at her again despite what had just happened in a court of law.

Criminal courts are almost certainly Mr Trump's least preferred environment since few of his standard tactics work well there. Indeed, many of his closest legal associates now face disbarment precisely because they followed his preferred stratagems in legal proceedings, where such shenanigans are not well tolerated outside the white-collar civil proceedings that he has been used to.

Even then, New York State isn't through with its least-favourite son.

New York's attorney general, Letitia James, is suing Mr Trump, much of his family, and their private company on civil charges of systematically misrepresenting their assets by overvaluing them to investors and undervaluing them for tax purposes. Her ultimate goal is to not merely regain assets but to bar Mr Trump and his two older sons, Donald Jr and Eric, from ever running any businesses in the state again. That civil trial is scheduled to begin this October.

Special Counsel Jack Smith led the DOJ's investigation into Trump, which includes 37 counts. EPA

Arching over it all is special prosecutor Jack Smith's apparent upcoming additional federal charges related to the January 6, 2021 insurrection and Mr Trump's broader failed coup effort following President Joe Biden's electoral victory in November 2020. Mr Trump recently received a so-called target letter from the Justice Department, reportedly advising him that he may well face charges of conspiracy to defraud the US, obstruction of an official proceeding, and, to the surprise of many, conspiracy to defraud people of their constitutional rights. There is little doubt another federal indictment will follow soon enough.

This, logically, seems to focus on the more sinister underlying efforts to overturn the election results – such as the plot to promote “fake electors” from Republican-controlled states that would secure victory for Mr Trump over Mr Biden despite the election outcome – than just the more dramatic mayhem of January 6.

Mr Trump also seems likely to face charges in Georgia on related state-level crimes, given that he was recorded pressuring senior officials to “find” exactly the number of non-existent votes he needed to defeat Mr Biden there.

These charges are merely looming, so there is no indication yet when expected additional trials might begin. But the first Republican primary debate is scheduled for August 23, kicking off the nomination campaign. Republican primary voting begins with the Iowa caucuses and New Hampshire primary in January 2024 and culminates in March. The Republican National Convention will be in Milwaukee from July 15-18, potentially right in the middle of the current front-runner’s varying criminal trials and other legal woes.

Only if he survives all that comes with his potential rematch with Mr Biden. Suffice it to say, the developing calendar smashing together Mr Trump's political ambitions and legal exposure doesn't seem like the optimal context for victory.

As the legal schedule now stands, his criminal trial in Florida may begin mere days after the end of the one in New York. It's already taking its toll.

In the last quarter of fund-raising, most of Mr Trump's donation dollars went not to his presidential campaign, as most donors no doubt expected, but to an affiliated “political action committee” that serves mainly to steer funds into paying his mounting legal bills.

Mr Trump's rapidly filling, unavoidable criminal trial agenda could well hammer his presidential ambitions with a continuously running, self-authored anti-Trump TV ad campaign that will most likely only get more damaging as the 2024 presidential election approaches.