Will the Trump Lawfare succeed? Part 1

If the left leaning Mainstream Media globally is to be believed, former US President Donald Trump could end up in jail for many years after multiple indictments for various offences. An indictment is an American term meaning being charged with an offense of some kind. An indictment does not indicate guilt and in the context of the prosecutors doing the charging, Trump’s opponents are engaging in what is called lawfare which is a single word description for politically motivated legal cases.

Lawfare in fact is very common in 3rd world countries and in despotic regimes. Even the most infamous dictators in history would shroud their persecution of the perceived enemies of the state behind a patina of fake legality via corrupt or co-opted judges and prosecutors. Lawfare is less common in the Anglophile Common Law and western European Roman Law democracies outside of the corporate world. The exception in the west is the US where politicised prosecutions have been commonplace because the Judiciary and the Executive branches at every level of US government are highly politicised. Understanding the process in the US is an important backdrop to understanding the current Trump lawfare.

Whilst the US Federal Constitution formally separates the three branches of government (Legislative, Executive and Judicial) with a series of counter weighing checks and balances (that are mirrored in all the States’ Constitutions), unlike the rest of the Anglophile world that follows the Westminster model, almost all US judges at every level are political appointees. The sitting President gets to appoint Federal Judges, Federal Courts of Appeal judges and of course the Justices of the Supreme Court. These appointments must be ratified by the Senate but, with some notable exceptions, unless the nominee has some glaring and provable fatal flaws, a Senate controlled by the opposing party of the President usually ends up confirming the President’s choices. This is mirrored at the State level with the sitting Governor appointing State Appeal and State Supreme Court judges and usually the Superior Court judges in larger cities with some states mirroring the Federal system with a state Senate confirmation process. Elected County Supervisors oversee the appointment of County court judges and elected Mayors usually nominate Municipal or City Court judges. There are some jurisdictions that have merit panels staffed by lawyers and ex-judges and all state, county and municipal judges are subject to confirmation election by voters every 2 years at each Presidential and mid term election. Bad judges who make high profile seen to be incorrect decisions or who become embroiled in controversy and won’t resign, can and are voted out of office. In addition to the partisan judges are the partisan prosecutors, the most notable being District Attorneys. Most crimes are handled at the county and city level and charges are normally brought by DAs offices in County or Municipal courts. District Attorneys operate at either the County or City level, but they are an elected position and almost all DAs have a partisan political affiliation. Left leaning cities/counties elect Democrat DAs and right leaning cities and counties elect Republican DAs.

It is known that the incoming President selects his Cabinet from the ranks of parochial allies. Ditto at the State level, the Governor appoints departmental heads although in most states, the most high-profile State government positions are elected. What is less known is that the politicisation of the bureaucracy goes three layers deep below the level of Cabinet Secretary (equivalent of a NZ Cabinet Minister). On average the Federal Government in Washington DC has over 30,000 political appointees that change when an Administration is voted out of office. There simply is no equivalent of this level of politicisation in any other 1st world democracy.

American history is rife with examples of the law enforcement controlled by one party attempting to bring down politically motivated prosecutions against their political opponents. What is different with the Trump cases is that he is the first ex-President to be indicted and the sheer scale of the lawfare is also unprecedented.

Why are the Democrats engaging in lawfare on this scale with Trump?

1 – To tie Trump up in court to interfere with his ability to campaign,

2 – To financially drain him with civil fines that encroach on his financial empire and campaign funds,

3 – To try to make him electorally toxic because of possible prosecutions,

4 – To try and get Trump removed from the ballot in the 2024 Presidential election and

5 – To force him to give up and retire to avoid all of the above.

Generally speaking, prior attempts at lawfare usually results in success for the party of the prosecutors hence why it is undertaken. However, Trump is no ordinary politician as we shall see.

The seven lawfare cases being brought against Trump divide into 3 distinct categories and I will examine each one in summary and the likelihood of success in each case. I will cover the 14th Amendment and two civil cases in Part 1 and I will cover the four criminal indictments in Part 2. All seven cases have the same modus operandi in terms of the tactics used by Trump’s political opponents:

First – The judges presiding over each case (with one exception) have been carefully chosen for their impeccable left-wing credentials. They are all appointees of Democrat Presidents or Governors. They have a track record of being hyper partisan and have previously presided over lopsided politically motivated trials giving verdicts and sentences that have been crafted to damage or restrict a Republican or right leaning defendant.

Second – Like the judges, the prosecutors have also been hand selected for their hyper partisan biased ideologically left leaning orientations and have also been appointed by Democrat Presidents or Governors. In all cases, the prosecutors have previously brought notoriously partisan, exaggerated and even trumped up (excuse the pun) charges.


Various Democrat elected officials in a number of states have attempted to use section 3 of the 14th Amendment to the Constitution which states that at any candidate that “has engaged in insurrection or rebellion” shall be barred from office. The amendment was passed after the Civil War ostensibly to bar successionists from seeking federal office. On the premise that Trump supposedly incited rebellion on January 6th 2021, his opponents feel this clause should apply.

Democrat Secretaries of State or County Supervisors who oversee the administration of election ballots at the state and county level and who also oversee relevant state election laws, ruled Trump was ineligible under this clause and then attempted to remove him from their ballots for first their Republican primaries and then the General Election in November. Trump’s campaign or local Republican party organisations sued in local courts to oppose these measures. In thirteen states (Arizona, Alaska, Nevada, New Jersey, New Mexico, New York, Oregon, South Carolina, Texas, Virginia, West Virginia, Wisconsin and Wyoming), these attempts were ruled against by state Appellate or Supreme courts on the grounds that Trump has never been convicted of the offense of insurrection. He was not convicted in his second impeachment trial by the Senate on this matter and even in the January 6th related charges he faces in Federal Court brought by Special Counsel Jack Smith (discussed in Part 2), Trump was not formally charged with any Federal insurrection indictments. It is important to note that even Democrat appointed judges in liberal states have ruled against these attempts which underscores the flimsiness of the arguments.

However, the Democrat controlled Colorado Supreme Court overruled the decision of the Colorado Court of Appeal that threw out the case forcing Trump to appeal to Federal court. Given the explosive potential of this issue, the Supreme Court (SCOTUS) agreed to immediately take up the case directly rather than have it go through the two prior layers of Federal appellate courts. Similarly, the Maine Secretary of State has ruled Trump ineligible, and that case is pending the outcome of the Colorado Supreme Court v Trump case at SCOTUS. Just yesterday a Democrat Cook County (covering metropolitan Chicago) circuit judge in Illinois has just removed Trump from that county’s GOP Primary ballot.

How will the Colorado case fare do you think? Well various legal analysts on both sides of the political fence who read the tea leaves from the SCOTUS appearance of both legal counsel teams were pretty united in stating how weak the Colorado case was, how it poorly it was argued and that the aggressive questioning of the Colorado attorneys from even the three reliable liberals on the Court portent a lopsided defeat for the Colorado case. The only argument is whether it will be a 0 – 9 or 1 – 8 ruling. Once ruled on at SCOTUS, the Maine and Illinois attempts will be dropped and that will end this “Hail Mary” attempt to remove Trump from ballots.


(i) E Jean Carroll defamation suit

E Jean Carroll is an 80-year-old former Elle Magazine advice columnist from New York City who, in a column in New York Magazine in 2019, accused Donald Trump of raping her in a dressing room at prestigious Bergdorf-Goodman Department store in NYC sometime in the mid-1990s. As it turned out, the NY Police Department never pressed any criminal charges of rape or sexual assault against Trump because Carroll never made a formal complaint to the NYPD despite there being no statute of limitations on historical criminal rape cases and even after being invited to by NYC Mayor Bill de Blasio (3′ 20″). There are a number of compelling reasons why, if she had laid a police complaint, it would not lead to any charges including:

  • The length of time it took for her to come forward with her claim,
  • She had no witnesses to the fact that Trump and she were together in the store,
  • Her description of the dressing room was so inaccurate making her claim logistically impossible,
  • There was no CCTV footage of Trump entering the store,
  • When questioned, Carroll couldn’t even remember what year the alleged incident happened,
  • Carroll was unable to recall ever telling any friends or family about such a momentous event,
  • The designer dress suit by Donna Karen that Carroll claimed to have been wearing at the time of the alleged attack was made several years later according to NY Times fact checkers ,
  • Carroll claimed to have had the dress forensically tested and yet during the defamation hearing, she never brought the dress or the test into evidence nor pushed for Trump to provide a DNA test to prove her claim.

Trump vehemently denied the claim and, in true Trump fashion, wryly said, “anyway, she isn’t my type”. Since Carroll made no formal criminal complaint, financially backed by Trump-hating left wing billionaire activist and  Democrat donor Reid Hoffman, Carroll embarked on a campaign to change the law in the state of New York to extend the statute of limitations for the bringing a CIVIL complaint of battery. Carroll was prominent in the campaign to change the law and on the very day after the amended law came into effect in 2022, Carroll filed a civil battery suit in the notoriously left-wing Manhattan Municipal Court where she knew she’d have a left-wing jury and a Democrat appointed judge sympathetic to her cause. She also sued Trump for defamation claiming his strenuous and aggressive denials damaged her reputation by impugning her honesty.

The trial was conducted over April and May 2023 when the sympathetic jury did indeed find Trump civilly liable for battery but specifically noted that the verdict DID NOT make a finding of guilt of rape and awarded defamation damages in the order of $83 million.

Trump has denied any wrongdoing and has appealed the verdict. What are the chances of him getting the verdict overturned on appeal, if not at the New York Appellate and Supreme Court but more likely at Federal Appellate Courts? Based on the following that occurred or did not occur during the trial, Trump has copious and strong grounds for a reversal of the decision on appeal:

  • In any defamation defense, the truth is always the best defense and Trump has truth on his side.
  • The undisclosed conflict of interest between Judge Lewis Kaplan and Carroll’s attorney Roberta Kaplan (no relation) in that Lewis was Roberta’s mentor when they both worked the same Manhattan law firm.
  • Carroll’s allegation bears a striking resemblance to an almost identical plot line of an episode of Law and Order: SVU, a popular US police drama set in NYC which NBC screened in 2012 some 7 years before her first public allegation.
  • Perhaps the most egregious miscarriages of justice in the trial were the various times the judge ruled as inadmissible various critical pieces of evidence that proved that Carroll was sex obsessed, had stalked other high-profile businessmen and had made multiple prior false claims of rape. Some of these are shocking:

* One of the few bits of evidence allowed was a 2017 Facebook post of Carroll’s where she rhetorically asked “Would you have sex with Donald Trump for $17,000? Even if you could a) give the money to charity? b) close your eyes? And he’s not allowed to speak.”

* In a 2019 interview with Anderson Cooper on CNN after the allegations were made public, Carroll said that “most people think of rape as being sexy” and so bizarre was her conduct in the interview that Cooper immediately cut to an ad break.

* Carroll had falsely accused multiple other men of raping her including: a babysitter’s boyfriend, a dentist, a camp counselor, an unnamed college date, an unnamed boss and most significantly, Les Moonves former CEO of CBS News.

* She said on CNN in an interview “I do not know if the President ejaculated” – a most extraordinary statement for a supposed rape victim to say (see 2′ 40″)

* Carroll has tweeted a number of sexually charged Tweets that were bordering on inappropriate

Trump was allowed 3 minutes on the stand and could answer only a few selected and curated Yes No questions. Neither he nor his attorney were able to bring up any of this damning evidence as to the track record and mind set of Trump’s alleged accuser. On the fact alone that his right to proper self-defense was arbitrarily abrogated by the capricious decisions of a highly partisan Trump hating judge, this verdict will be easily overturned.

(ii) New York Attorney General fraud suit

The very definition of a politically motivated prosecution is demonstrated in the $250 million civil fraud case brought by New York State Attorney General Leticia James against Donald Trump, his sons Don Junior and Eric Trump and the Trump Organization. Letitia James literally campaigned for the AG’s office on a platform to “get Trump” and any cursory search of social media will unearth clips of James frequently bragging before mostly sympathetic Democratic audiences of her intention.

AG James alleged that Trump overvalued his assets to obtain loans from banks and to get more favourable insurance contracts that he later went on to profit from. The case was heard by Manhattan Supreme Court Judge Arthur Engoron, a jurisdiction known to be very left leaning and hostile to Trump. In addition, Engoron’s wife posted a series of nasty anti-Trump memes on social media and when Trump made appearances in court, Engoron was visibly hostile to Trump and ended up fining him twice for contempt of court after Trump breached gagging orders from speaking publicly about the case.

Engoran found, without any jury trial (extremely rare for a case so large), that the Trumps had indeed committed fraud and so the trial was held merely to decide on the amount of the fine. It is clear from the penalty handed down ($355 million) that Engoron had already made up his mind to do the bidding of AG James by attempting to destroy the Trump’s New York base of business with not just punitive fines but a 3 year ban on doing business in the state of New York and applying for loans in the state.

Trump has commenced the appeal process, in and of itself financially onerous because the court will impose a 10% interest loading taking the total penalty to be allowed on appeal to $450 million. Whilst Trump is wealthy enough to pay this, it would drain his cash reserves and likely require the fire sale of assets. The most likely pathway he will take is to use a court Bond to cover the fine plus interest where normally he only has to find 10% of the amount being bonded or $45 million. That still hurts but is more doable for Trump.

What is the likelihood of this punitive award and the onerous restrictions surviving an appeal? Not high because of the unusual features of this case, setting aside the obvious political bias. These include:

* the fact that all New York based real estate developers to some extent exaggerate their net worth when applying for loans. It is actually a global practice. It is why banks and lenders rely on their own estimates of property values and it’s why properties used as security for large commercial loans are independently valued and the banks make a decision on the amount to advance and terms based on such independent valuations. All of the loans that Trump obtained were issued on that basis.

* This case is probably the world’s first fraud case where there is no defrauded party. Indeed, every single loan and insurance product that Trump obtained using his Statements of Position were repaid on time and in full with never even so much as a missed or late payment and not a single financial institution suffering any loss at all. The notion of fraud is a victim who is out of pocket due to alleged fraudulent activity. To the contrary, various senior bank staff testified at the trial that not only was the Trump account flawless and blemish free from a banking perspective, but that Trump was considered an enormously valuable (so-called ‘whale’) client whose loan business was sought after by banks. A number of business commentators have noted this absence of any fraud loss as a major flaw in the AG’s case.

* This prosecution is utterly unique in New York legal history. Despite there being literally hundreds of high-end property developers who have built thousands of properties in the state over many decades, almost all of whom engaged in similar loan application conduct as Trump, not a single case of fraud of this nature has ever been brought. A number of financial commentators have remarked that this verdict will have an enormously chilling effect on the property development market in the state as developers will move their sights, funding and projects to states less hostile to entrepreneurial development activity.

* Judge Engoron ruled that Trump’s Statements of Position were fraudulent. Trump’s lawyers brought to the stand Eli Bartov, a renowned accounting professor of the Stern Business School at NYU who said of Trump’s financial statements submitted to get loans, “I’ve never seen a statement that provides so much detail and is so transparent. The footnotes provide an awesome amount of information.”

* Perhaps the single most staggeringly biased and ill-judged decision in this whole case, and on which perhaps alone would be ground for appeal, was the decision of Engoron to value Trump’s flagship property in Palm Beach, Florida (Mar-a-Largo) at a miniscule $18 million basing this off the Palm Beach County property tax valuation as an exhibit of the type of over valuation ‘fraud’ that he claimed Trump engaged in.

In order to understand the sheer ineptitude and blatant bias of this valuation, some knowledge of Palm Beach and its unique real estate is important.  First off, as in NZ, local government property tax valuations (like the ratable value used by QV in NZ for what was commonly called the GV or Government Valuation and used for basing local council rates) are almost always well below market value, sometimes massively so.

Palm Beach is one of the most prestigious addresses in all of the US and of the highest value are properties in the southern and most narrow part of the long thin island that comprises Palm Beach that are large enough to straddle the width of the island and thus have a frontage on the Atlantic Ocean beach and the Lake Worth Lagoon between Palm Beach and West Palm Beach on the mainland. Indeed, the name of Trump’s property Mar-a-Largo means “sea to lake” in Spanish. Mar-a Largo is one of a handful of properties with this unique feature.

Trump paid $7 million for the property in 1985, admittedly in a distressed sale situation, and added a 20,000 sq ft (2,000m²) ballroom to the 17-acre (almost 7 ha) site making the total size of the buildings 62,500 sq ft (6,250 m²). It has extensive facilities as befitting a large luxury country club with pools, tennis courts and private access to the beach and lagoon. In 2018 Forbes magazine estimated the value at $350 million and upped that estimate to $500 million in 2022.

As an example of the massive prices being asked for properties in this part of Palm Beach, a property 2 miles (3 kms) south of Mar-a-Largo on Ocean Boulevard is on the market for $174 million for a house size of only 18,000 sq ft (1,800 m²) and on a section about ¼ the size of Mar-a-Largo. Famous prominent top end Palm Beach real estate agent Lawrence Moens is said to have told Trump he’d list MAL for $750 million.  Letitia James charged Trump with fraud saying he spruiked the value by $250 million and that was her fraud claim above Judge Engoron’s claimed value of $18 million. For $18 million you might be able to buy the garden shed of one the houses in this area!

Aside from the massively chilling impact a verdict like this will have on New York property development, expert legal and real estate opinion on the verdict has been scathing:

* MSNBC (a left wing cable network implacably opposed to Trump) Legal Analyst Lisa Rubin quoted an Associated Press analysis of all historical fraud cases brought in the state of New York going back 75 years and found not a single precedent for Engoron’s penalty given there was no proven or even victim claimed fraud loss..

* A prominent Palm Beach real state broker told the NY Post “It’s utterly delusional to think that property is only worth $18 million.”

* Esteemed legal commentator Jonathon Turley, Professor of Public Interest Law at George Washington University, wrote an excoriating assessment of Engoron’s penalties in “The Hill” where he stated, “The damages in my view are excessive and absurd after the court acknowledged that no one lost a dime in these exchanges. Indeed, the “victims” wanted to do more business with Trump and made handsome profits,” and later on he opines on the fate of this verdict, “The size of the damages is grotesque and should shock the conscience of any judge on appeal. Even if the Democrat-appointed judges on the New York Court of Appeals were to ignore the obvious inequity and unfairness, the United States Supreme Court could intervene.”

* Acclaimed Constitutional Historian Victor Davis Hansen agreed with Trump that the massive fine likely violates the 8th Amendment against excessive fines.

* Professor Steven Calabresi of the Northwestern Pritzker School of Law commented in Reason magazine: “Ms. James and Judge Engeron have essentially turned a vaguely worded New York State law into a modern day Bill of Attainder targeted at Donald Trump both for political gain and because they despise his political views and desperately want to call his truthfulness into question as he runs for President of the United States in 2024. In doing this, they have violated Trump’s First Amendment right to freedom of speech and of the press; his Fifth Amendment right not to be deprived of liberty or property without due process of law; his Fifth Amendment right not to have property taken away from him except for a public use with just compensation being paid; his Eighth Amendment right not to be made to pay an excessive fine; his Article IV, Section 2 right as a citizen of Florida to do, make, and enforce contracts in New York on the same terms as are other New Yorkers; and his Fourteenth Amendment right to be free to pursue an occupation without unnecessary and burdensome regulation.”

I’ll end this analysis with two great ironies:

1 – Facing a hostile backlash from New York business owners and property magnates, New York Governor Kathy Hochul said the quiet part out loud. In trying to reassure this skeptical audience that NY had not become a hostile place to do business, she claimed that no one ought to fear this verdict because it was unique against Trump further sealing the fact that this was a political witch hunt.

2 – Lest any Trump supporters among you fear that Trump may yet lose appeals and be stripped of $500 million of his worth, in the same week of the verdict, the SEC cleared the path for Trump’s popular social media platform Truth Social from previous market capital raising restrictions thus catapulting, with the stroke of a pen, the value of Trump’s holding in Truth Social to around $6.5 billion

These civil fraud cases are particular darlings of the left and the Never Trump RINOs but they will never amount to a hill of beans in their ability to stop Trump from running for the Presidency.

In Part 2 I will cover the four criminal indictments.

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