Chapter 10: Autocrats United

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Chapter 10: Autocrats United

Tyranny, like hell, is not easily conquered; yet we have this
consolation with us, that the harder the conflict, the more
glorious the triumph. —Thomas Paine

In the stark offices of Kyiv’s Center for Civil Liberties, Oleksandra Matviichuk and her team meticulously document war crimes committed during Russia’s invasion of Ukraine. By early 2025, they’ve documented over 68,000 cases since Russia’s 2022 full-scale invasion.1 This Nobel Peace Prize–winning organization has tracked Russia’s crimes against Ukrainian civilians since the 2014 annexation of Crimea.²

I remember watching Louise’s face as we saw news reports of mass graves in Bucha: the shock, horror, and tears. “This is Putin’s work,” she whispered. “But Trump helped make it possible.”

She was right. The bombs falling on Ukrainian cities have many authors, Putin chief among them. But they’re also the indirect result of American acquiescence to autocratic power by Donald Trump, whose presidency marked the first major retreat from democratic values in modern American history.

The Autocrat’s Apprentice

To understand Trump’s deference to dictators, we must return to that mansion in Queens where Fred Trump taught his son that kindness was weakness, and the world was divided into “killers” and losers. These weren’t casual encouragements but imperatives in a household where success meant dominance, not happiness or community contribution.

This foundation was reinforced by Roy Cohn’s scorched-earth tactics, detailed in Chapter 2, which taught Trump that appearance trumped reality, attack was always preferable to defense, and admitting error was tantamount to surrender.

As explored in Chapter 3, Trump’s lifelong commitment to creating the illusion of success found its perfect political expression in his admiration for autocrats. Dictators are masters of façade, projecting strength while their countries crumble, building monuments while their people suffer. Their gold-plated palaces and carefully orchestrated displays of adulation represent the ultimate version of Trump’s own gold-plated brand: power as performance, strength as spectacle.3

The Putin-Trump Partnership Deepens

It was February 12, 2025, when Trump held his first direct call—at least one that we knew about—with Vladimir Putin since Russia’s 2022 invasion of Ukraine. Louise and I watched the news when the story broke, both of us shaking our heads in disbelief.

I thought to myself, this is also how democracies die, not with tanks in the streets, but with phone calls between a real dictator mentoring a man who desperately wants to become one.

Since that ninety-minute conversation, Trump’s rhetoric on Ukraine has increasingly mirrored Putin’s.4 By April, Trump was publicly declaring that “Crimea will stay with Russia” and claiming “Zelenskyy understands that,” functionally legitimizing Russia’s criminal annexation of that territory in clear violation of international law.5

The consequences were immediate. Trump’s envoy Steve Witkoff—a diplomatically naïve billionaire real estate developer with zero diplomatic experience—has now met repeatedly with Putin in Moscow without an American translator or experts from the State Department or intelligence agencies. He’s been pushing a peace plan that would force Ukraine to surrender significant territory while apparently also (according to press reports) laying plans for a Trump Tower Moscow.6

It’s a pattern we’ve all seen repeatedly since Trump first stepped onto the nation’s political/electoral stage in 2015: autocrats praising Trump’s ego while he surrenders America’s principles. This isn’t diplomacy: it’s capitulation to a foreign power disguised as some sort of bizarre deal-­­­making.

Corporate America’s Autocracy Dividend

And make no mistake: autocracy pays, at least for the autocrats and their oligarch supporters. That’s one aspect of the dirty little secret behind Trump’s affinity for dictators; his corporate backers love how the autocrats he wants to become like crush labor unions, eliminate environmental regulations, and slash corporate taxes while giving them immunity from investigation or prosecution so long as they suck up to and continue to fund the “big man.”

When Trump praises Putin, sides with Saudi Crown Prince Mohammed bin Salman after journalist Jamal Khashoggi’s murder, or lauds China’s Xi Jinping for making himself “president for life,” he’s simply voicing what America’s corporate elite view as the natural order of things: hierarchy and money over democracy. (It’s worth noting that the only democratic institutions in a corporation are the unions; everything else resembles an ancient kingdom with CEOs as kings and senior executives and board members as lords and ladies.)7 American corporations have poured trillions into China (in addition to moving much of our manufacturing base there) despite its authoritarianism, profit daily from Saudi Arabia’s repressive regime, and many continued operating in Russia even after its illegal annexation of Crimea in 2014.8

Take ExxonMobil under Rex Tillerson, for example, who had Putin’s Order of Friendship pinned on his chest in Moscow before becoming Trump’s secretary of state during his first term. His company lobbied the Obama administration aggressively against Russia sanctions following the Crimea invasion; those sanctions would have blocked a potential $500 billion oil deal.9 During Trump’s first term, the new president pushed to immediately lift those very sanctions.

This wasn’t just a twisted, anti-American-values foreign policy; it’s a naked business strategy. Trump’s administrations—particularly this second one—represent the ultimate fusion of corporate and autocratic interests characteristic of nations undergoing the transition out of democracy and into kleptocratic autocracy.

The Helsinki Surrender

I also remember watching that shocking Helsinki press conference in 2018. Louise and I were as stunned as the rest of the world was while Trump stood beside Putin and chose the word of a former KGB spymaster and psychological warfare expert over America’s own intelligence agencies. That wasn’t just a diplomatic blunder: it was groveling submission that humiliated America on the world stage. The same man from Queens who revels in bullying leaders from smaller democratic allies like France or Ukraine folded like a cheap suit in Putin’s presence.10

Standing beside the Russian dictator, Trump sided with Putin over America’s own intelligence agencies—the world’s best—on Russian interference in the 2016 election. It was a public display of fealty by the supposed leader of the free world, bowing to kiss the ass of an autocrat who had explicitly attacked American democracy.11

Trump’s relationship with Putin (and other autocrats) continues to worry international and domestic observers. In March 2025, Trump and Putin began laying groundwork for a ceasefire in Ukraine, with international observers and democracy advocates both worrying and warning that Trump may accept a deal finalizing Russia’s illegal invasion and forcing territorial concessions from Ukraine.12

What our corporate media consistently fails to report is how Putin’s approach to governance—state capture by oligarchs, attacks on independent media, intimidation of the legislative and judicial branches, persecution of political opponents—has become the clear template for Trump’s vision of America.

It’s not just that Trump simply admires Putin; he wants to become Putin.

The Saudi Connection: Arms and Influence

Trump’s embrace of Saudi Crown Prince Mohammed bin Salman (MBS) reveals his willingness to trade the interests of America for personal profit. When Washington Post journalist Jamal Khashoggi was murdered inside the Saudi consulate in Istanbul, the CIA concluded with high confidence that MBS personally ordered the assassination.13

Trump’s response? He vetoed congressional efforts to block arms sales to Saudi Arabia and ignored legal requirements to determine MBS’s responsibility. “I saved his ass,” Trump later boasted to journalist Bob Woodward. “I was able to get Congress to leave him alone.”14

Trump’s relationship with MBS has reached disturbing new heights in 2025. In January, MBS pledged to invest $600 billion in the United States, which Trump immediately demanded be “rounded up” to $1 trillion, saying, “I think they’ll do that because we’ve been very good to them.”15

The quid pro quo became clear in April 2025, when reports emerged that Trump plans to offer Saudi Arabia an arms package worth over $100 billion during his May visit.16 This comes despite MBS’s continued human rights abuses and the kingdom’s refusal to hold anyone accountable for Khashoggi’s murder.17

More troubling still is how Saudi Arabia has become central to Trump’s foreign policy, hosting talks between US and Russian officials and mediating international negotiations.18 It’s a perfect illustration of how autocracy’s influence has metastasized under Trump: the country responsible for Khashoggi’s brutal murder now sits at the center of American diplomacy.

The corporate media’s coverage was tepid, presenting it as merely “unconventional diplomacy” rather than complicity in murder to protect weapons contracts worth billions to American defense contractors. The same pattern plays out with Trump’s embrace of Egypt’s el-Sisi, Turkey’s Erdoğan, and other authoritarians, putting corporate profits above human rights and democracy.

The White Christian Nationalist Connection

There’s another pattern in Trump’s favored autocrats: they almost all use white Christian nationalism as a rallying cry against multiculturalism, immigration, and religious diversity.

Hungary’s Viktor Orbán has become the poster child for this approach, dismantling democratic institutions while claiming to defend “Christian civilization.” After Trump’s 2016 victory, Orbán jubilantly declared: “We have received permission from the highest position in the world to put ourselves in first place.”19

This white Christian nationalist agenda serves as perfect cover for the economic agenda of autocrats, concentrating wealth in the hands of loyal oligarchs while convincing average citizens that immigrants, minorities, and (Jewish) “globalists” cause their economic struggles, not corruption and crony capitalism.20 By wrapping authoritarianism in Christian religious virtue, leaders like Orbán dismantle democracy while claiming to defend traditional values.

Trump also deploys this same playbook in America, using racist and Christian nationalist rhetoric to energize his base while implementing economic policies benefiting the ultra-wealthy corporate elite who fund his campaigns.

Kim Jong Un: The Nuclear “Friend”

Trump’s bizarre fixation on North Korea’s dictator continues unabated. In January 2025, he promised to “reach out to him again,” despite their previous summits yielding no actual denuclearization. By March, Trump was publicly referring to North Korea as a “nuclear power,” effectively abandoning decades of US policy by accepting Kim’s nuclear arsenal as legitimate.21

What Trump doesn’t mention is that North Korea has dramatically changed its posture since their last meeting, sending thousands of troops to support Russia’s war against Ukraine and strengthening ties with China. Kim is certainly watching Trump’s Ukraine diplomacy with keen interest, calculating how many concessions he might extract from a president desperate for theatrical “wins.”

The Republican Autocrat Tradition

Trump didn’t invent the Republican Party’s fondness for dictators. Nixon embraced Latin American dictatorships, Reagan supported apartheid South Africa and set up strongman governments in Central America, and Bush rehabilitated Uzbekistan’s murderous regime after 9/11.22

What Trump did was drop the pretense that these alliances had anything to do with “national security” or “strategic interests.” He openly admires these regimes because of their authoritarianism, not despite it.

Republican leaders increasingly celebrate this shift. At the 2021 Conservative Political Action Conference (CPAC), they displayed a golden statue of Trump, that being a perfect symbol of the party’s transition from a conservative political organization to a personality cult modeled on authoritarian movements worldwide.23 That golden idol was no joke; it represented a party abandoning political principles for devotion to a single man.

The Autocrat Strategy: A Dangerous Pattern

These aren’t isolated incidents: they represent a coherent strategy that prioritizes relationships with dictators over democratic allies. Trump’s approach to foreign policy is fundamentally transactional, viewing international relations through the same lens as his real estate deals: whoever offers the biggest financial package gets the best treatment, regardless of their human rights record.

The pattern is consistent:

· Praise the dictator personally while ignoring their abuses.
· Focus on financial transactions over democratic values.
· Bypass professional diplomats in favor of inexperienced loyalists.
· Capitalize on American retreat to pursue personal business interests.

As one expert noted regarding Trump’s relationship with Arab autocrats: “There’s no policy process, there’s no interagency process. You have the cell phone number of someone. . . . You can either make a call or WhatsApp and get stuff done, and that’s basically the way they do business.”24 That’s precisely the problem; democratic governance depends on process, transparency, and institutional guardrails that Trump consistently undermines.

Media Normalization of the Unthinkable

“Putin is a killer,” Bill O’Reilly said to Trump in a 2017 interview.

“There are a lot of killers,” Trump shot back. “You think our country’s so innocent?”25

In a functioning democracy with responsible media, this statement alone—a sitting president equating America with Putin’s murderous regime—would have dominated headlines for months and ended a presidency. Can you imagine if Clinton, Obama, or Biden had said such a thing?

Instead, within days the news cycle had moved on, the incident becoming just another “Trump being Trump” moment in an endless stream of normalized abnormality.

This is also how democracies die: gradually, to paraphrase Hemingway, then suddenly. The corporate media’s failure to maintain any sort of prolonged focus on Trump’s autocratic behavior and admiration for dictators stems from a profit-driven corporate media and social media system where outrage drives revenue, but sustained critique threatens access and advertising dollars.26

I see it on my radio show with a depressing regularity. Listeners call in stunned by Trump’s latest embrace of one or another dictator, but within twenty-­four hours, some new outrage pushes it from the headlines. This dangerous psychological numbing has set in even among those who recognize the threat.

American Implementation of the Autocrat’s Playbook

Trump’s embrace of foreign autocrats and their ways of governing their nations has become official US policy through:

Information Control: Following Putin’s (and Hitler’s, Stalin’s, Orbán’s, and Mussolini’s) playbook, Trump calls critical reporting “fake news” and labels journalists as “enemies of the people,” rhetoric that leads directly to death threats against reporters.27

Loyalty Tests: Just as autocrats demand personal loyalty above duty to the nation, Trump purges officials who show more loyalty to the Constitution than to him personally.

Weaponizing Law Enforcement: Following the autocratic principle that law exists to serve power rather than constrain it, Trump repeatedly—and publicly—pressures his Justice Department and FBI to investigate opponents and protect allies.28

This isn’t just rhetoric; it’s the methodical installation of autocratic governance, enabled by Republican leaders who’ve abandoned principled conservatism for proximity to wealth and power.

The Grassroots Resistance

Despite this grim picture, there’s hope. Americans across the political spectrum are increasingly recognizing Trump’s threat and are mobilizing to protect our democracy.

Civil servants risk careers to blow the whistle on abuses. Judges—including many Republican appointees—uphold the rule of law against unprecedented pressure. Journalists persist in reporting truth despite threats. And millions of ordinary citizens defend democratic values at the ballot box and in their communities.

Oleksandra Matviichuk reminds us that our democracy isn’t just a system of government; it’s a mindset, a commitment to human dignity that must be actively defended. “Because it is not NATO that Putin fears, it is democracy. Dictators fear the idea of freedom.”29

Why It Matters

When Matviichuk documents Russia’s war crimes in Ukraine, she’s representing a global community that is struggling across the world against rising authoritarianism on four continents.

Donald Trump didn’t invent autocracy but he embraces it, legitimizes it, normalizes it, and has been aggressively importing its methods into our government. His embrace of corrupt dictators aren’t simply diplomatic failures; they are, in fact, existential threats to democracy itself across the planet.

What kept tyrants in check over this past century was American leadership: the example of a nation committed to the foundational principles of democracy articulated by our Founders, fought and died for by generations of American patriots, with the awesome economic and military power we’ve built over the centuries to back them up. Trump has systematically undermined each of these democratic bulwarks, thus helping empower a global authoritarian resurgence that threatens to reverse a century of worldwide democratic progress.30

It’s almost impossible to overstate the danger. When the world’s most powerful democracy openly sucks up to or does corrupt business with dictators like Putin, Orbán, and MBS, it doesn’t just damage America’s standing: it emboldens autocrats and wannabe autocrats globally to crush dissent and loot their own nations, knowing they’ll face no meaningful consequences from America.

The damage to our nation and the rule of law will outlast Trump’s presidency. Democracies eroded, alliances frayed, and norms shattered can’t be instantly restored by an election or even the impeachment of Trump. History tells us that the global balance of power, once tipped away from democratic governance and redirected toward authoritarian models, requires enormous effort to rebalance.

Fred Trump taught his son that the world is divided into killers and prey. Roy Cohn taught him that appearance matters more than reality. Trump’s business career taught him that you can fail repeatedly and still claim victory. Putin taught him that lies and the corruption of business elites can work. And now, as president again, Trump is teaching the rest of the world’s autocrats and wannabe dictators a deadly lesson: America is no longer democracy’s defender. Instead, we’ve become autocracy’s enabler.

This isn’t just politics. It’s a war for democracy’s soul. And we’re all on the front lines.