Why Trump’s Legal Issues are Finally Serious

Former President Trump is currently mired in several messes. There’s the investigation into election meddling during his infamous call to the Georgia Secretary of State, lawsuits preventing his banks from sharing his financial information over tax evasion, his organization being found guilty of tax evasion, and a half dozen lawsuits around allegations of sexual impropriety. For a transparently unethical man who has made a career out of working the system, the number of Trump’s legal issues is truly staggering.

While Trump has been the political and legal version of Jason Vorhees with seemingly nothing able to really hurt him, the Mar-a-Largo documents, recent courtroom losses, and the apparent shifting public perception of the former President amongst Republicans have potential to end his nigh-unbelievable streak of Houdini-esque escapes.

For prosecutors and opposing counsel, Trump has bobbed and weaved himself into a corner. Now they can unload, as attorneys are rightfully scared off from being retained by what I — as an attorney who has dealt with all types — would describe as a “nightmare client.” He famously stiffed Giuliani on legal fees and notoriously breaks the first rule of being in legal trouble: keep your damn mouth shut. Therefore, undercutting his ability to draw top-tier legal talent undermines him in court.

The Historic Defense to Trump’s Legal Issues

For anyone familiar with Donald Trump’s business or legal history (or read Maggie Haberman’s book), his typical opening strategy for any problem is familiar: attack, attack, and attack. Should this fail or appear to be the wrong move for him, he will (allegedly) try to charm prosecutors or regulators, occasionally offering them incentives to go easy on him like professional opportunities. Or, he might have ethically-ambiguous attorneys that can best be described as “fixers” (like Roy Cohen or Michael Cohen) who handle a matter informally. All the while, attorneys still willing to represent him will file any motion they can think of, i.e., the request for the special master to review the Mar-a-Largo documents that were only recently (but soundly) rejected on appeal.

This, in addition to hosting unrecorded meetings and going so far as tearing up the notes of attorneys at said meetings; (allegedly) demanding employees make sketchy transactions yet never putting anything down in writing; and demanding complete loyalty from the people he employs, Trump was rightfully described as a creature similar to a “mafia boss” by former FBI Director James Comey.

The mafia boss game worked fine in New York real estate for decades (just Google Sanford Solny). Still, the disorganized horrorshow that is the NYC real estate industry where you can say “sue me” after not paying your subcontractors does not prepare one to play in the big leagues. For example, Donald was taken aback by the fact that, unlike local leaders in NYC, the federal and Supreme Court judges face incredible public scrutiny and are more invested in their long-term careers. This makes them far less likely to help him with an illegal or unethical favor than the typical corrupt New Yorker looking for a way to cash out.

Granted, the former President has escaped consequences time and time again: the Mueller investigation into connections between Trump and Russian election interference; the first impeachment for abuse of power and obstruction of Congress over Trump’s interference with funding for Ukraine; investigations into hush money paid to porn stars, one of which was made out of campaign funds… However, this was all done with high-ranking Republicans running a full-court interference that actively discouraged prosecution.

Previously, Trump was able to ragdoll the Republican Party, i.e., getting Rep. Kevin McCarthy to show up at Mar-a-Largo to kiss the ring after criticizing Trump publicly for his role in the Jan. 6th insurrection. Or (my favorite) pushing a sweaty, uncomfortable Sen. Ted Cruz into phone banking for him after publicly insulting his wife’s appearance.

The Shifting Sands of Trump’s Influence

Unfortunately for Donald, MAGA no longer carries the political currency that it once had. To be sure, politicians like Ted Cruz and Kevin McCarthy (as well as their Democrat equivalents) would likely cannibalize their own mothers for a position of power – how else can you explain that Mike Pence, a former right-hand-man of Trump for whom gallows were erected with Trump’s encouragement, would continue to support him (or, at the very least, continue to withhold his criticism)? However, these guys will point in whichever direction the political winds blow.

In analyzing these political winds, Trump’s political rise isn’t surprising. The GOP has encouraged the less rational amongst their numbers with copious amounts of red meat, base-affirming politics, and culture wars until they no longer care what the traditional Chamber of Commerce Republicans have to say. Then, having so thoroughly encouraged and developed the political infrastructure and power for organizations like the Tea Party or Freedom Caucus, they force-fed the MAGA Mogoi like a foie gras duck after midnight. Now they’re shocked that a bunch of Gremlins in red hats have taken over their party so extensively that they can’t keep the crazies that alienate more rational Republicans off the ballot.

In making every enemy on his way up, screwing people over while on top, and sacrificing others to save his own skin on the way out, Trump didn’t have a single friend in Washington that was not forced into compliance by a rabid MAGA base. However, the midterm elections have revealed glaring weaknesses.

(Photo Credit: Michael M. Santiago/Getty Images)

Trump’s Slackening Hold on the GOP

Modern midterm elections, with the notable exception of George Bush Jr. coasting on 9/11 momentum, always go against the current President as nearly every problem the country faces at the time is considered his fault. In the recent midterms, although Republicans won in general, they did so by a much smaller margin than was predicted by long-running historical trends. On top of that, MAGA candidates did disproportionately worse (i.e., Trump’s pick for Georgia, Herschel Walker, losing a very-winnable Senate seat), while non-MAGA candidates were at least able to approach expectations much more often — objective proof of the political wind generated by Trump being on a strong decline.

Previously, prominent conservative figures have offered Trump a bewildering amount of support and cover, i.e., Tucker Carlson making Ted Cruz his bitch on live television for offering even mild criticism of the former President’s worst actions.

Now, the New York Post summarized the current Republican establishment’s sentiment towards Trump in their page 26 writeup of his candidacy announcement, “Florida Man Makes Announcement.” The former President’s previous defenders that could help him cry “witch-hunt” are now making their 2024 primary calculations and trying to figure out when their party will hit an anti-Trump tipping point. As we inch closer to the optimal time for the candidacy announcement, this pressure will only ratchet up, and sooner or later, the candidates will fight for the position of who turned on Trump first.

The Reality of Trump’s Legal Issues

With the political interference outside of the court waning and his cases building up evidence, pressure, and synergy as documents made public in one case may inform and be offered in another, it’s difficult to see how Trump can continue to escape consequences.

The fact that those who were scared for their lives in the Capitol building now look to twist a knife into him when he’s too wounded to destroy their careers permanently is not helping him. Nor is the fact that any attorney who prizes their license, reputation, or freedom will avoid him as defending him legally has cost attorneys all three. One day, he may check under his bed and find Liz Cheney sharpening her knives with a broad, unnerving grin, and there won’t be a Giuliani, McCarthy, or MAGA mob to throw at her.

This is the part of the horror movie where the Crystal Lake teenagers have done an ungodly amount of damage, and I think he’ll eventually go down for the count. Still, I’d be surprised if he doesn’t play whatever desperate move he believes he can pull off for one last jump-scare.

Think of it like our country’s sweeps week, led by a tired, grotesque reality star desperately clinging to enough political relevance to give his prosecutors a migraine.