A Philosophical and Investigative Essay On the Lamentable Necessity of Making Maximum Utility of Dirty Tricks in Contemporary US Politics

Part I: Dirty tricks are immoral and illegal, but fun and effective as well. The Harris campaign's failure to build a unit of veteran smear artists may return Trump to the White House, sources say.

Roger Stone, Trump’s crony and former unofficial advisor to his 2016 campaign, during an earlier stage of his illustrious career. Screenshot of cover of a 1996 issue of The Star.

Last Monday, Charlotte Clymer, a well known trangender activist and communications strategist posted an article at her Substack publication, Charlotte's Web Thoughts, that sharply criticized the Washington Post’s for its decision not to endorse a candidate in the 2024 presidential election, writing that the newspaper had an obligation to endorse Kamala Harris because Donald Trump’s “flagrant disregard for the Constitution and the rule of law” made him unfit to hold office. Clymer’s timing proved to be unfortunate because later that same day, the Philadelphia Inquirer reported that AllVote – a murky political group she works for that doesn’t reveal who its donors are and whose goal is to “mobilize progressive voters” – had been behind a covert voter suppression texting scam aimed at decreasing GOP turnout in Pennsylvania, a key swing state where the outcome could determine who wins the White House.

There’s been no evidence that ties Harris’s campaign to the scam, but Clymer is a diehard Democrat and affiliated with a political organization called “Women for Harris-Walz.” Assuming the Inquirer’s story was accurate, and there’s nothing that indicates it wasn’t, Clymer’s work with AllVote was expressly intended to undermine the integrity of the US electoral system and this year’s presidential race. 

That’s bad and utterly indefensible, from an ethical perspective anyway. But let’s put that aside for a moment and evaluate the situation from the purely utilitarian standpoint of a Harris campaign official or an ordinary citizen who’s rooting for her to defeat Trump. 

To be clear, I loathe both and this is a simple abstract philosophical exercise that explores the pros and cons of dirty tricks, but if viewed from the practical rather than moral side of things, is what Clymer did less wrong than it may appear at first glance? Upon further reflection, might her work even have been right, particularly if AllVote had gotten away with the plot and its handiwork delivered the votes Harris needed to win Pennsylvania and, ergo, the presidency?

A strong case can be made to support that position, which I’m about to lay out, and it doesn’t only cover corner-cutting or flat-out law-breaking Democratic consultants could – and should in my opinion – have put into play to steal this year’s election no matter what the voters want, but also exonerates whatever hypothetical, morally repugnant skullduggery Republican operatives have dreamed up and implemented in hopes of doing the same. I used the word “hypothetical” advisedly as I have no proof Trump’s official and unofficial 2024 strategists have used underhanded let alone illegal methods during this year’s campaign.

However, if I were to hazard a guess based on history, common sense, and the GOP’s full bullpen of available henchmen – to name only a few, Roger Stone, one of the most legendary dark arts specialists ever unleashed in American politics; Ric Grennell, Trump’s devoted, ruthless former Acting Director of National Intelligence who the RNC and a pro-Trump Super PAC have paid substantial sums of money for unknown purposes; and the promising relative up-and-comer Arthur Schwartz, who one source I spoke with compared unfavorable to Stone, saying the latter “is cartoon evil but Schwartz is the real thing” – I’d propose that the possibility Trump’s campaign hasn’t launched secret plots aimed at destroying destroy Harris, and may very well be implementing one at this very moment, certainly can’t be ruled out. 

Indeed, that very possibility, remote or not, is at the heart of my argument, because black ops have been employed in US politics since the nation’s founding, and for a very good reason: they work. “Voters say they don’t like negativity, but then they’re drawn to negative ads,” longtime Democratic strategist Rodell Mollineau, a former advisor to the pro-Biden Super PAC Unite the Country, told The Hill earlier this year. “So if getting down in the mud a little is going to better demonstrate to voters what’s at stake, then so be it.”

As Mollineau’s remarks suggest, secretly managing a dirty tricks operation is as integral to political consulting as orchestrating a gangland hit is to a mob bossdom, so if one side hasn’t incorporated the tactic into the campaign playbook, it’s handed the other side a huge advantage. When your opponent is Trump, who understands this full well and acts accordingly, failing to assemble a trusted team of remorseless sociopaths who don’t question orders or ever ponder whether their actions are right or wrong because they don’t know the difference, is tantamount to unilateral disarmament. 

Yet that’s exactly what Harris has done, sources from both parties have told me. That her campaign has the necessary financial and human resources required to conduct anti-Trump sabotage operations but has failed to so – and not because of some silly, misguided, high-minded moral calculation or fear of criminal prosecution, but a simple lack of imagination and planning – makes the vice president’s failure all the more unconscionable.

“Kamala’s inner circle is filled with relatively straightlaced, conventional political consultants but what she needs most in a race this close are dirtbag fixers, and Trump has both types but the ones who have his ear are the dirtbag fixers,” an experienced strategist who’s worked for several presidential candidates told me. “It’s costing her.”

Portrait of FBI Special Agent G. Gordon Liddy, one of his government jobs before being hired to work for the Nixon administration’s Plumbers "special investigations unit" and was later tasked to organize the burglary of DNC headquarters at the Watergate building. While working for Nixon’s 1972 reelection campaign, Liddy also proposed kidnapping anti-war protest organizers and luring Democratic officials to a house boat in Miami stocked with prostitutes in order to take secret photographs that could be used to blackmail them. Photo via Wikimedia Commons/Public Domain.

As I’ve just demonstrated, there’s no reasonable moral objection to a presidential candidate or any other seeker of elected office to cheating, lying, and stealing his or her way into political office. The only possible drawback associated with making extensive use of scumbaggery on the campaign trail is that employing a staff top-heavy with sociopaths makes perfect sense when all that matters is winning by any means necessary no matter how many people get hurt, but that’s not necessarily the best approach to governing, yet victorious candidates will invariably feel compelled to bring the staffers who helped them win public office into government with them, which can create all sorts of problems.

But that’s one of those bridges in life that can be crossed later, so for now let’s turn to defining what dirty tricks are, what they can achieve when handled by skilled professionals, and what steps need to be taken by candidates before black bag operations commence to ensure no one goes to prison other than possibly innocent underlings the conspirators skillfully framed without their knowledge ahead of time as a precautionary measure in the event things go south and will have no hope of proving their innocence.

To start then, dirty tricks are sometimes conflated with opposition research, but the two fields are entirely different. Casual political observers tend to have a romantic idea about the second of the two, and imagine it involves the use of sophisticated methods and spy devices that net previously unknown, highly damning information that is leaked to the media and forces opponents to end their campaign. 

The reality is far more banal. The standard end product of opposition research is typically a large collection of newspaper clippings and documents, virtually all that can be found with a Google search, that’s supplemented in some of the better packages I’ve perused, with items easily obtained by using Lexis or another online news and public records service. 

That was seen in the recent oppo package on JD Vance that was allegedly stolen by foreign hackers and mainstream media outlets declined to publish, but was disclosed by Ken Klippenstein. I’m glad he did it and would have done the same had I gotten it first, but the contents didn’t contain anything notably surprising or detrimental to the Trump-Vance campaign.

Dirty tricks are essentially what most people think opposition research is and is far likelier, if done properly, to bring about a devastating political impact. Traditional tactics include stealing information that reveals opposing candidates’ campaign strategies or can be used to defame them, discredit the enemy by planting phony stories in the media about then or ginning up whisper campaigns, preventing or discouraging the other side’s voters from going to the polls, as AllVote was seeking to do, and rigging the election result by hacking electronic voting machines or stealing paper ballots.

In days past, high-grade material was frequently procured by private detectives and low-grade grifters with criminal histories who bribed disgruntled ex-spouses, bartenders, hotel maids, political staffers, reporters, and any other source with access to the requisite goods. Nowadays, though, high-end political warfare has become a predominantly white collar profession, with a lot of the work contracted out to established political consultants and operatives, though ones who are less risk-averse than the industry norm. A growing share has also been farmed out to lawyers at blue chip firms, who can cite attorney-client confidentiality, or extremely expensive high end corporate intelligence firms. 

A major advantage of hiring this more recent breed of practitioners is that they’re much more reluctant to rat out their clients than the earlier low-end elements from the earlier generation. They also usually possess sufficient political clout and financial resources that they’re able to refuse to answer queries from law enforcement or comply with subpoenas issued by grand juries, or at least stall for so long that by the time they do it no longer genuinely matters because it’s too late to reverse the election outcome and the client-candidate who hired them was inaugurated to office long ago. 

To minimize the risk of exposure, any reasonably savvy political candidate or political operative would know not to put anything on paper that could sink them and outsource operational management to an experienced professional who isn’t on payroll or have any official connection to the candidate, and the designee in turn would employ individuals of the same sort. If proper steps are taken to make sure there are at least six degrees of separation between the candidate and the crime, the FBI or local police may be completely certain President A or Congressman B is a lying, cheating filthy scoundrel and apprehended the manager and crew who performed the actual grunt work, but without any hard evidence that can be traced back to the conspirators guilty parties, the authorities won’t be able to do anything about it.

That’s historically been the outcome of 99 out of 100 political corruption investigations, which end with all parties skating unless they did something incredibly reckless or stupid. That’s what doomed President Richard Nixon, who implicated himself by recording damning conversations with White House staff, and whose most trusted advisors employed reckless morons like former FBI agent G. Gordon Liddy and ex-CIA officer E. Howard Hunt to lead the White House Plumbers "special investigations unit" that tried to identify leakers in the administration and then tasked them to organize the burglary at DNC headquarters in the Watergate building – and even Nixon didn’t do prison time but merely had to resign in disgrace in 1974, but then live another two decades have the pleasure of watching the entire political and media establishments fully restore him to a place of honor in polite society. 

Since then, powerful elected officials have gained so many layers of protection from facing charges for authorizing sleazy dirty tricks operations – or corruption schemes or any other type of criminal activity – via laws they passed themselves or Supreme Court rulings, that the risk of being charged for participating in an illegal scheme, as an organizer or beneficiary, is so negligible that there’s no decent excuse for not giving it a go. I’ll flesh that out in the second part of this series when I review the history of dirty tricks in modern US political history, and detail the brazenly criminal and   hideously degenerate capers of Republican and Democratic dirty tricks specialists whose exploits reaped them fortune and fame, including induction into the American Association of Political Consultants Hall of Fame for a few. 

Meanwhile,in a few rare cases, lower-level operatives that were more vulnerable and disposable were indicted and prosecuted. To take an example from the 2020, consider the case of Russian-born Florida businessmen Lev Parnas and Igor Fruman who were intermediaries between the laughable grifter Rudy Giuliani and a corrupt Ukrainian gas tycoon during a failed effort to dig up dirt on Democratic nominee Joe Biden for the Trump campaign’s use. 

The two businessmen had another initiative underway at the same time that was unconnected to the quest for exploitable material on Biden, but Giuliani, who was working as Trump’s personal attorney at the time, or someone in Trump campaign circles should have been at least partly aware of, Parnas and Fruman were funneling illegal campaign donations from foreign sources to about a dozen Republican members of congress in an apparent quid pro quo for their votes on bills of interests to those behind the scheme. Parnas and Fruman were eventually indicted and sentenced to 20 months and a year in the can, respectively; no one else was ever charged as part of either dirty op, including the elected officials, against the fervent wishes of FBI counterintelligence agents who investigated the bribery cases. 

Sidney Blumenthal at event at New America Foundation think tank in 2008, during his years of faithful service as as hatchet man and smear artist for Bill and Hillary Clinton. Photo via Wikimedia Commons/Public Domain.

An case that dates to an earlier era involves Sidney Blumenthal, a hatchet man for Bill and Hillary Clinton who smeared Monica Lewinsky for the former and Barack Obama for the latter when she faced off against him in the 2008 Democratic presidential primaries. Blumenthal didn’t commit any evident criminal conduct like Parnas and Furman, but was guilty of appalling ethical conduct that didn’t lead to long term reputational damage, but instead to career and financial rewards.

The upshot here is that Harris and her top advisors could have perfectly well gambled on a stratagem to inflict significant pain on Trump with near zero fear of exposure. Had they had the imagination and ambition her team could have rolled the dice on a more daring but nevertheless low-reward, high-risk schemes – let’s say operations where the miscreants retained by the Harris campaign’s designated cutout to carry out the operation had no way to obscure all signs of their wrongdoing, so it was probable someone would calls the cops – that could have killed the GOP nominee’s hopes in one fell swoop. 

Entirely doable options that immediately spring to mind, which are offered only for illustrative purposes, range from staging a break-in at a small town highschool in order to steal the personal records of Donald Trump Jr’s teen mistress who the campaign had reason to believe was pregnant, or it became necessary to murder Jeffrey Epstein’s former chief pilot because he doubled the initial price for a treasure trove of XXX-rated photos of the former president and the late-pedophile joyfully masturbating each other aboard the “Lolita Express,” and Harris and her advisors had concluded after running multiple simulations that the hired guns who’d be paid to  do the dirty work wouldn’t have enough time to slay the victim, dismember his corpse with a chainsaw so the parts could be carried out in garbage bags, and scrub clean the blood off the floors and walls of the basement so the crime might go undetected, because his wife never left him alone at home for more than 15 minutes, hence his remains would regrettably have to be left in the bathtub.

All of which begs the questions posed earlier, namely, why did Harris dilly-dally for so long in taking the low road when so many alternatives as simple as the high school burglary and basement slay operation were at hand, especially when it was all but certain the Trump gang was brainstorming proposals round the clock for the best underhanded tricks to destroy her politically and personally? And now that it’s too late to act, how will Trump’s overwhelming superiority on the campaign battlefield of dirty ticks play out next Tuesday? 

Coming Monday in Part II: The Golden Age of Dirty Tricks, Historic and Active Exemplars of the Tradecraft, and the Specialists in Trump’s Campaign Arsenal Who May Come to Power With Him if He Wins Back the White House