Trump’s Pattern of Betrayal Pt 1: Why Ukraine Must Prepare for the Worst
Years of Trump's pathology are on display for easy reminder of what comes next
(Kyiv apartment building destroyed in July 31, 2025 attack. Photo by Chris Sampson)
(Dear Reader, Since January 2022, I’ve been documenting Ukraine’s war independently, filming and photographing across the entire country to bring you an unfiltered view of events as they happen. Your paid subscription keeps this work independent and sustainable, free from editorial constraints. It also helps us build out our NatSecMedia bureau to be more responsive to the stories you need to see. Thank you for supporting independent journalism from Ukraine—and please reach out if you’d like to collaborate or help expand our coverage.)
I’ve spent years documenting a disturbing pattern in Donald Trump’s relationship with Ukraine and Russia. The evidence isn’t speculative—it’s meticulous, documented, and repetitive. Trump will betray Ukraine again because he already has, multiple times, and nothing in his psychology or behavior suggests this will change. In fact, it will get worse because other vultures surround him with their own ambitions that are far more suited for Russia’s corruption model, than Ukraine’s ambition to rise out of the Soviet rusted experience.
Trump has a record on Ukraine from his first term: he didn’t help them to the point of being impeached for it, and instead spent his presidency kissing up to Putin. This isn’t speculation about future behavior—it’s documented history we must not ignore.
The Research Behind the Warning
Since launching NatSecMedia from Kyiv in 2022, where I’ve been based throughout Russia’s full-scale invasion, I’ve maintained a front-row seat to the consequences of the very policies I’d spent decades documenting. I have also met many of the people at the center of the history we’ll explore in the subsequent posts.
In context, my work in news began in 2001 at KPFT 90.1 FM in Houston, then evolved through CheneyWatch—an accountability project tracking the crimes of the Bush administration—and later expanded to document the Trump presidency’s systematic dismantling of democratic norms and national security protocols.
The years investigating Cheney through CheneyWatch provided another education: the absence of accountability mechanisms for executive branch abuses. The pattern repeated consistently—public outrage would emerge around torture, rendition, war profiteering, and constitutional violations. Politicians would mobilize that outrage to secure votes, then return to standard operations once elected. The news cycle moved forward. New anchors replaced the old. Current events displaced historical crimes. The systematic abuses documented in extensive public records simply faded from the discourse, unaddressed and unpunished.
Over the years, I’ve served as chief of research on four books examining asymmetric threats to democratic institutions through Trump’s ambitions, authored Hacking ISIS, and wrote the foreword to Putin’s Asymmetric Assault on Democracy in Russia and Europe: Implications for U.S. National Security (Skyhorse Publishing). That foreword to the Senate report that examined how the Kremlin weaponizes information, corruption, and political influence to destabilize the West—patterns I’d been tracking across multiple public databases, articles, and dedicated websites that chronicle the components of these operations.
The research wasn’t abstract theorizing. It involved building comprehensive archives of primary sources, maintaining public records of financial transactions, cataloging disinformation campaigns, and documenting influence operations as they occurred. Further, it relied on too many resources that were not in the umbrella of ‘government narratives’ including Trump’s own words.
When Trump’s relationship with Russia emerged as a critical issue during the 2016 election, I documented how the Russian hacker campaigns evolved before the DNC hack and then how he benefited from Russian hacking operations. The subsequent work explored Putin’s hybrid warfare tactics against Europe and America—the sophisticated blend of military force, disinformation, cyberattacks, economic coercion, and political subversion that Russia deploys to undermine democracies without triggering conventional war. This included deep dives into each country being targeted and each separatist group being nurtured by Russia.
But it was while researching the details of Trump’s first impeachment that the full scope became unavoidable. The investigation revealed something more sinister than a policy dispute. It exposed a president who viewed Ukraine not as a strategic ally in a critical geopolitical struggle, but as a tool—something to be leveraged, extorted, and discarded when it no longer served his immediate needs. This transactional worldview, combined with his documented affinity for Putin, created a dangerous reality for Ukraine.
Being in Kyiv now, watching Ukrainians defend their democracy against the very authoritarianism I’d been documenting for years, the research stopped being just data points and websites. It became lived reality. The patterns I’d traced through financial records, diplomatic cables, and public statements were playing out in air raid sirens, in the faces of refugees, in the determination of a nation refusing to be erased.
The work of documentation continues—not as an academic exercise, but as a witness to what happens when democratic institutions fail to heed the warnings written in their own public record.
The First Term: A Chronological Record of Betrayal
Did Trump Go on the Offensive for Ukraine During His First Term (2017–2021)?
No. The Trump administration did not go on the offensive for Ukraine in any significant military, strategic, or rhetorical sense during his first term. The revisionist claim that Trump “gave Ukraine lethal weapons” serves as deliberate misdirection from a four-year record of systematic undermining, political manipulation, and outright sabotage of Ukrainian sovereignty—all while Ukrainian soldiers continued dying in a war that Trump’s allies and operatives helped enable.
Pre-Presidency: The Manafort Connection
Before Trump even took office, his campaign chairman Paul Manafort personified everything corrupt about the Trump-Ukraine relationship. Manafort wasn’t just any political operative—he was the American consultant who spent years whitewashing Viktor Yanukovych, the Kremlin-backed Ukrainian president who fled to Russia after the Euromaidan Revolution in 2014. Manafort earned millions lobbying for Yanukovych’s Party of Regions, helping legitimize a regime that systemically looted Ukraine, suppressed democratic movements, and steered the country toward Putin’s orbit.
When Yanukovych’s security forces massacred over 100 protesters during the Revolution of Dignity in February 2014, it was the culmination of the authoritarian project Manafort had helped build. After Yanukovych fled, Ukrainian investigators uncovered ledgers documenting $12.7 million in undisclosed cash payments to Manafort—money that came from the same corrupt networks now supporting Russian-backed separatists in Donbas.
Trump hired this man to run his presidential campaign. Not despite his work for Yanukovych—but likely because of the very connections and tactics that made him successful in Ukraine’s oligarchic underworld. Manafort brought Kremlin-friendly operatives, messaging strategies, and political instincts directly into Trump’s inner circle. His presence sent an unmistakable signal: Trump’s campaign, and later his administration, would be friendly to the very forces Ukraine was fighting against.
Manafort’s August 2016 departure from the campaign—forced by revelations about his Ukraine lobbying—did nothing to change Trump’s orientation toward Russia and Ukraine. The damage was done. The connections were established. And Trump’s affinity for Putin, combined with his hiring of Putin’s preferred consultant, revealed where his loyalties actually lay.
July 2016: The RNC Platform Sabotage
Even before Trump took office, his campaign actively worked to weaken American support for Ukraine at a critical moment. At the 2016 Republican National Convention, Trump campaign advisor JD Gordon led efforts to water down the GOP platform’s language on Ukraine. The original platform called for providing “lethal defensive weapons” to help Ukraine defend itself against Russian aggression. Gordon, acting on behalf of Trump’s campaign, successfully changed this to the much weaker “appropriate assistance.”
This wasn’t a minor semantic adjustment—it was a policy signal. At a time when Ukrainian soldiers were dying daily fighting Russian-backed forces in Donbas, Trump’s team was ensuring the Republican Party wouldn’t commit to meaningful military support. Gordon later confirmed he acted based on Trump’s pro-Russia views, telling investigators that Trump didn’t want to escalate tensions with Moscow. Delegates who supported the stronger Ukraine language were overruled, setting the tone for Trump’s transactional, Kremlin-accommodating approach to Ukrainian sovereignty.
The RNC platform fight revealed something crucial: Trump and his advisors viewed robust Ukraine support not as a moral imperative or strategic necessity, but as an inconvenient obstacle to Trump’s desired rapprochement with Putin. Ukrainian blood was an acceptable price for Trump’s geopolitical fantasy.
December 2017–2019: The Javelin Sales
In December 2017, the Trump administration approved the first sale of FGM-148 Javelin anti-tank missiles to Ukraine—a paid foreign military sale, not a donation. The $47 million package included 210 missiles and 37 launchers, accompanied by strict storage and usage requirements. The missiles were to be kept in western Ukraine, far from the front lines in Donetsk and Luhansk.
Heather Nauert, State Department Spokesperson (Dec 2017): “U.S. assistance is entirely defensive in nature, and as we have always said, Ukraine is a sovereign country and has a right to defend itself... [The U.S. provides] enhanced defensive capabilities to help Ukraine build its military long-term, defend its sovereignty, and deter further aggression.”
The sale’s political framing emphasized deterrence, not operational deployment. The Defense Security Cooperation Agency repeated this line in its March 2018 delivery statement: “This proposed sale will help Ukraine build its long-term defense capacity to defend its sovereignty and territorial integrity.”
Even inside the Pentagon, officials treated the Javelins as a strategic signal to Moscow, not a tool to change the battlefield. Training took place in secure storage facilities. No missiles were cleared for front-line use.
Wess Mitchell, Assistant Secretary of State for European and Eurasian Affairs (testimony, 2018): “The Javelins and other lethal weapons are designed not for first use but to deter Moscow from encroaching on Ukrainian territory.”
A second, smaller sale followed in 2019: 150 missiles and two launchers for $39 million, with identical conditions. There were no long-range weapons, no air defenses, and no offensive systems. In essence, Washington had paid for deterrence theater—”lethal aid” without lethality.
(Russian tank decimated by Ukrainian forces on the western side of Kyiv, April 2022, Photo by Chris Sampson)
The message was clear: Ukraine could defend itself just enough to avoid total collapse, but not enough to win. Just enough to keep dying slowly while Trump played footsie with Putin on the world stage.
August 2017: The Sanctions Charade
In August 2017 Trump signed CAATSA (Countering America’s Adversaries Through Sanctions Act), the legislation that imposed sweeping new sanctions on Russia’s defence and intelligence sectors, and gave Congress review rights over any presidential easing. However, the way he signed it was telling. In a signing-statement, Trump said: “While I favour tough measures to punish and deter aggressive and destabilizing behavior by Iran, North Korea, and Russia, this legislation is significantly flawed.” He further added that the bill “encroaches on the Executive Branch’s authority to negotiate.” He signed the law without ceremony, behind closed doors, voicing strong objections—signaling reluctance even as he signed.
On August 2, 2017, he called the Russia sanctions bill “significantly flawed.” Years later, he described a new sanctions bill as “totally at my option,” adding that he could “terminate totally at my option.” In essence, he treated sanctions as personal leverage rather than consistent elements of national strategy.
The administration delayed implementation of key provisions under CAATSA, creating uncertainty among allies. Trump’s public statements—calling NATO “obsolete,” suggesting Russia be readmitted to the G8, and siding with Putin in Helsinki—undercut the credibility of U.S. deterrence. These were not mere “mixed signals” but consistent indications that he saw sanctions as optional and primarily political.
For Ukraine, the implications were profound. Sanctions and allied unity form a critical part of deterrence against Russian aggression. When the U.S. president publicly questioned why the U.S. should care about Ukraine while its soldiers died in trenches, it weakened confidence in the coalition supporting them. The enforcement of sanctions became a hollow performance—strong on paper, weak in conviction.
Yes, the Trump administration technically enforced sanctions, but the enforcement lacked conviction. He treated sanctions as negotiation tools, not policy. Standing beside Putin in Helsinki, questioning NATO, and expressing irritation at CAATSA’s limits all signaled that the U.S. could not be relied upon to maintain pressure on Moscow. For adversaries like Russia, such inconsistency was encouragement.
Sanctions work when allies act in coordination and the target believes enforcement is certain. Trump’s ambivalence undermined both. Though thousands of sanctions were technically imposed during his term, his public stance made clear they were a reluctant measure. For Russia, the message was: wait it out. For Ukraine, it was another betrayal—this time by rhetoric as much as by policy.
2017–2021: The Giuliani-Parnas Shadow Operation
While official U.S. policy nominally supported Ukraine, Trump’s personal attorney Rudy Giuliani and his associate Lev Parnas ran a shadow foreign policy operation designed to manipulate Ukrainian politics for Trump’s benefit. This wasn’t diplomatic engagement—it was a pressure campaign that treated Ukraine’s government as a tool for manufacturing dirt on Trump’s political opponents.
Giuliani and Parnas worked to:
Remove U.S. Ambassador Marie Yovanovitch, a career diplomat and anti-corruption advocate, because she was seen as an obstacle to their schemes
Pressure Ukrainian officials to announce investigations into Joe Biden and Hunter Biden, regardless of evidence or merit
Spread conspiracy theories about Ukrainian interference in the 2016 election, echoing Kremlin disinformation designed to deflect from Russia’s documented cyberattacks
Undermine legitimate anti-corruption efforts in Ukraine by conflating them with Trump’s political vendettas
Parnas’s text messages and documents, released during the impeachment investigation, revealed the staggering scope of this operation. Giuliani wasn’t conducting diplomacy—he was conducting extortion, threatening to withhold U.S. support unless Ukraine publicly damaged Trump’s likely 2020 opponent. Ukrainian officials, desperate for American backing against Russian aggression, found themselves caught between defending their sovereignty and appeasing Trump’s political demands.
This shadow operation bypassed the State Department, the National Security Council, and every institutional safeguard designed to prevent foreign policy from becoming a vehicle for personal enrichment and electoral advantage. It reduced Ukraine—a country fighting for survival against Russian imperialism—to a pawn in Trump’s reelection strategy.
2017–2021: No Offensive Vision, Only Managed Stalemate
Throughout Trump’s presidency, there were no U.S.-backed Ukrainian offensives, no strategic vision for victory, no serious diplomatic initiatives to reclaim Crimea or end the Donbas conflict. Trump’s approach amounted to managed stalemate: keep Ukraine alive enough that Republicans could claim they supported an ally, but not strong enough to actually defeat Russian aggression or reclaim territory.
Trump never visited Ukraine. He never delivered speeches championing Ukrainian sovereignty or democratic resistance. He never rallied NATO allies around a coordinated strategy to push back Russian expansionism. Instead, he promoted the debunked conspiracy theory that Ukraine—not Russia—interfered in the 2016 election, and that a Democratic National Committee server was somehow hidden in Kyiv.
This wasn’t just ignorant—it was actively harmful, lending presidential credibility to Russian disinformation designed to deflect from Moscow’s documented cyberattacks. Trump’s rhetoric consistently echoed Kremlin narratives, treating Ukraine as corrupt, untrustworthy, and unworthy of American support. Meanwhile, Ukrainian soldiers kept dying. Between 2017 and 2021, the war in Donbas continued, grinding through lives while the American president publicly questioned whether their fight mattered.
Trump also resisted deeper NATO commitments for Ukraine, viewing the alliance itself with suspicion and contempt. His transactional approach to collective defense—demanding European allies “pay up” while threatening to abandon Article 5 commitments—sent a chilling message to Kyiv: American support was conditional, unreliable, and dependent on Trump’s mood.
July 2019: The Extortion Scheme
In the starkest indictment of Trump’s Ukraine policy, he froze $391 million in congressionally approved security aid in mid-2019 to coerce President Volodymyr Zelenskyy into investigating Joe Biden and his son Hunter. This wasn’t a policy disagreement or bureaucratic delay—it was extortion. Trump leveraged desperately needed military assistance, approved by Congress with bipartisan support, to force a vulnerable ally to manufacture dirt on his domestic political opponent.
The details, revealed through the impeachment investigation, are damning:
July 25, 2019 phone call: Trump explicitly asked Zelenskyy to “do us a favor though” immediately after Zelenskyy mentioned wanting to purchase more Javelins, linking U.S. military support to investigations benefiting Trump’s reelection campaign
Shadow diplomacy: Giuliani ran a parallel foreign policy operation pressuring Ukrainian officials to announce Biden investigations
Aid freeze: Trump personally ordered the hold on security assistance through the Office of Management and Budget, overriding Pentagon and State Department objections
Public admission: Acting Chief of Staff Mick Mulvaney admitted in a press conference that aid was conditioned on investigations, then told reporters to “get over it”
Whistleblower exposure: The aid was released only after a whistleblower report surfaced and congressional pressure became overwhelming—not because Trump had a change of heart, but because he got caught
Testimony from career diplomats, National Security Council officials, and Pentagon leaders painted a consistent picture: Trump didn’t care about Ukraine’s security, NATO’s credibility, or Russian aggression. He cared about using Ukraine as leverage against Biden.
For Ukraine, the message was brutal: American military aid—the difference between holding the line against Russian aggression and territorial collapse—could be withheld on a whim if it served Trump’s interests. Ukrainian soldiers’ lives were bargaining chips in Trump’s domestic political schemes.
The impeachment revealed not just a constitutional crisis, but a blueprint for understanding Trump’s transactional view of Ukraine: not as a democratic ally defending itself against authoritarian invasion, but as a tool he could exploit for personal advantage. This wasn’t support. It was manipulation.
November 2019: Javelin Talking Point Becomes Political Shield
The phrase “We gave them Javelins” entered the American lexicon during Trump’s first impeachment, when he was accused of freezing $391 million in security aid—including Javelins—to pressure President Volodymyr Zelenskyy for political favors. To defend him, congressional allies framed the missile sale as proof of unwavering support for Ukraine.
Rep. Jim Jordan (House Intelligence hearings, Nov 2019): “President Trump is the one who provided lethal aid—Javelins—to Ukraine. The Obama administration refused.”
Lt. Col. Alexander Vindman, NSC Director for Ukraine (testimony, Nov 2019): “While the Javelins were provided, they were subject to storage requirements and never deployed to the front.”
The rhetorical inversion was complete: a commercial sale under restriction became the centerpiece of a “tough on Russia” narrative—used to obscure an aid freeze that directly endangered Ukraine’s security.
2022: Biden’s Policy Shift Changes Everything
When Russia launched its full-scale invasion in February 2022, U.S. policy changed overnight. The Biden administration lifted restrictions, transferring thousands of Javelins—not dozens—to Ukraine under emergency drawdown authority. These weapons became iconic in the early months of the defense of Kyiv.
Yet apologists retroactively credited Trump’s earlier sale for the battlefield success. What they omitted:
Trump’s Javelins remained in storage throughout his term
Ukraine paid for those weapons
The Biden administration delivered over 8,500 Javelins in the first six months of the war, a thirtyfold increase in scale
Lloyd Austin, Secretary of Defense (March 2022): “We have provided thousands of Javelin anti-armor systems, which have proven devastatingly effective against Russian tanks.”
Trump’s earlier “symbolic sale” had finally become tangible—but only after his exit from office and a total overhaul of U.S. policy.
2023–2025: The Resurrection of a Myth
By mid-2023, as domestic support for Ukraine became a partisan wedge, the “We gave Javelins” line resurfaced as a political weapon. Trump invoked it repeatedly in rallies and interviews to contrast his “smart, limited aid” with Biden’s “blank checks.” In July 2024 and again after his return to office in early 2025, he repeated the line to President Zelenskyy himself:
“Biden gave sheets; we gave Javelins.”
Right-wing commentators amplified the refrain to justify cuts to future military aid, portraying the 2017 sale as the pinnacle of prudent foreign policy. By October 2025, the phrase was deployed as historical revisionism, a way to claim credit for Ukraine’s defense while excusing disengagement.
First Term Conclusion: A Blueprint for Betrayal
Trump’s first-term Ukraine policy wasn’t support interrupted by scandal—it was systematic betrayal occasionally punctuated by symbolic gestures. From hiring Manafort to weakening the RNC platform, from running shadow diplomacy operations to withholding military aid for political extortion, Trump consistently prioritized his personal interests and Putin accommodation over Ukrainian sovereignty and security.
The “lethal weapons” narrative is a lie of omission, erasing context to manufacture a false equivalence. Trump didn’t champion Ukraine—he exploited it. He didn’t confront Russian aggression—he enabled it through weakness, mixed signals, and active undermining of American policy.
The claim that Trump “supported Ukraine more than Obama” by providing lethal weapons is a deliberate distortion designed to obscure years of systematic betrayal. Yes, Trump approved Javelin sales. But this cherry-picked fact ignores:
Hiring Yanukovych’s American consultant as campaign chairman
Weakening the 2016 GOP platform to avoid committing to meaningful Ukraine support
Delaying and undermining congressionally mandated Russia sanctions
Running a shadow foreign policy operation to pressure Ukraine for political dirt
Withholding $391 million in security aid to extort investigations into Biden
Promoting Kremlin conspiracy theories about Ukrainian election interference
Providing no strategic vision for Ukrainian victory or territorial restoration
Never visiting Ukraine or championing its cause in any meaningful way
Attacking NATO and questioning why America should support Ukraine
Consistently deferring to Putin in rhetoric and policy
Between 2017 and 2021, Ukrainian soldiers continued dying in Donbas—more than 2,000 additional casualties during Trump’s term. Trump gave no speeches mourning these losses. He announced no initiatives to end the war. He offered no strategic vision beyond keeping Ukraine weak enough not to provoke Putin, but alive enough to avoid political embarrassment.
The “We gave Javelins” narrative distills the essence of Trump-era foreign policy: performative toughness masking strategic paralysis. It is the story of weapons as props, deterrence as theater, and diplomacy as a branding exercise. And it reminds us how easily a paid sale of stored missiles can be spun into legend—so long as the soundbite fits the campaign trail.
When Trump defenders claim he “supported Ukraine better than Obama,” they’re counting on historical amnesia. The record tells a different story: one of corruption, manipulation, and betrayal, written in Ukrainian blood while Trump played geopolitical games with an adversary he consistently refused to challenge.
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