Rebecca Bennett: From Navy Test Pilot to Congress

Bennett discussed her path from military service to healthcare and ultimately to public office. Motivated by the September 11 attacks, she joined the Navy, deployed to the Middle East aboard the USS Nimitz in support of the Afghanistan war, and went on to become an experimental test pilot, helping develop and safely evaluate aircraft technology for the United States and its partners. After leaving active duty, she earned an MBA from Wharton and worked in healthcare, including oncology, gastrointestinal care, and women’s health.

Now running in one of the country’s most competitive congressional districts, Bennett emphasized the importance of putting country over party, confronting corruption, banning congressional stock trading, and getting dark money out of politics. She also discussed her campaign’s grassroots support, including more than 1,400 volunteers and 1.4 million voter contacts.

If elected, Bennett wants to focus on infrastructure and national security. She highlighted the Gateway Tunnel project, which is critical to commuters traveling between New Jersey and New York, and called for greater congressional oversight of the military and a more effective approach to defense acquisition. Drawing on her experience as a test pilot, she argued that the United States needs to rethink how it develops and fields military technology to meet 21st-century security challenges. She also stressed the need to protect women serving in the military and invest more seriously in women’s health.

Please donate to Rebecca’s congressional campaign, here. https://secure.actblue.com/donate/rebecca-bennett-1?refcode=avrb

Congressman Eugene Vindman: Ukraine, American Leadership, and Accountability

In the second half, Congressman Eugene Vindman joined us to discuss the growing pressure on Ukraine and the consequences of the Trump administration’s approach to the war. He described President Volodymyr Zelensky’s appeal to bipartisan members of Congress for continued American support, restored Starlink access, and additional air defense to protect Ukrainian civilians.

We discussed the damage that abandoning Ukraine could inflict on American credibility, our relationships with NATO allies and European partners, and U.S. national interests. The conversation also explored the dangers of allowing powerful private actors to influence decisions with profound consequences for people around the world. When American technology and services can be withdrawn at the whim of political leaders, other countries have reason to question whether the United States remains a reliable partner.

We then turned to the midterm elections and the need to hold the administration accountable. Eugene described the election as a referendum on a presidency characterized by what he calls the three Cs: chaos, cruelty, and corruption. He argued that rising costs, including grocery and fuel prices, have compounded the consequences of the administration’s policies and that voters deserve both accountability and a positive agenda to make life more affordable.

We closed on a principle that applies well beyond any one election: restoring public trust requires confronting corruption and restoring integrity to government. As Eugene put it, “You can’t have reconciliation without accountability.”

Watch the full conversation for a discussion of the next generati

on of veteran leaders, the fight to defend democracy at home and abroad, and what is at stake in the coming elections.

Please donate to Eugene’s congressional campaign, here. https://secure.actblue.com/donavsubstackate/

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Dear Readers,

I will be broadcasting live on Substack TODAY at 1:30pm ET with Rebecca Bennett and Representative Eugene Vindman. Our conversation will cover the issues voters care about this midterm season and the challenges facing the United States on a national scale. You won’t want to miss this!

Be sure to download the Substack mobile app and click here to view the broadcast.

Rebecca Bennett is the Democratic candidate for New Jersey’s 7th congressional district. She is a former Navy helicopter pilot, a mother of two, and has been endorsed by Emily’s List.

Eugene has represented Virginia’s 7th district since 2024. He is my (younger) twin brother and served in the Army. His service included years in the Army Judge Advocate Generals (JAG) Corps, where he served as an international law advisor in Iraq and later deputy legal advisor on the National Security Council.

According to recent reporting from the Wall Street Journal, the Russian government has proposed a trilateral meeting between Putin, Trump, and Xi Jinping to discuss the resolution of the war in Ukraine. Putin reportedly first raised the idea during an October 9th phone call with Trump, the same call that preceded the diesel deal and the subsequent shut-off of American intelligence sharing with Ukraine. The meeting would likely take place on the sidelines of the APEC summit in Shenzhen, China on November 18–19. Kremlin spokesman Dmitri Peskov has confirmed that discussions are underway, and a senior U.S. official said Trump has not agreed to attend but could be receptive. Ukraine would not be at the table. Ukrainian Foreign Minister Andrii Sybiha has stated that the proposed summit would only lead to more aggression from Moscow. When considering the decisions that the administration has made in recent weeks regarding American support for Ukraine and US-Russia rapprochement, it’s clear that Trump is both interested in this trilateral format and predisposed to deliver for Russia and China at the expense of Ukraine and almost certainly Europe and the United States.

I have long been a critic of the transactional approach taken by this administration and the numerous short-sighted decisions that have crippled Ukraine’s defense and needlessly torched American-European relations. This summit might very well augur something even more serious. It is completely plausible to describe the potential Putin-Trump-Xi meeting as the negotiated end to the post–World War II order and the definitive end of the American century. At Yalta in 1945, three leaders carved up postwar Europe, deciding Poland’s future without Poland at the table. But Yalta came paired with the founding of the United Nations and the institutions that would restrain great-power appetites for decades. A Putin-Trump-Xi summit would be Yalta in reverse: the same carving of spheres and the same absent victim, but this time dismantling the institutions rather than building them. Just as Yalta shaped the Cold War, the trilateral Putin-Trump-Xi conference will shape the inevitable conflicts of the near future.

Let’s consider what this meeting would mean for each of the proposed guests. For Putin, a trilateral meeting with Trump and Xi would be a clear PR victory that would affirm Russia’s desire to be viewed as a superpower. With Trump already literally rolling out a red carpet for Putin during the Alaska Summit, this meeting would be seen as another instance of the United States compromising its own efforts to isolate Russia in exchange for meaningless pledges from Putin. Additionally, the trilateral summit may deliver to Putin through diplomacy what Russia has failed to achieve militarily: the full capture of Donetsk Oblast and the capitulation of the Ukrainian government. It’s possible that the three heads of state come to the conclusion that a lasting peace can only be secured if Ukraine surrenders the Fortress Belt and surrounding territory. Any protest from Kyiv against this proposal may result in a combination of continued Russian military activity alongside new sanctions from the United States and China. No matter the outcome, Russia benefits from this trilateral meeting. I would also note that surrendering the Fortress Belt now, even for a truce, would compromise Ukraine’s security and leave Kyiv and the entirety of Ukraine vulnerable to the next attack from Moscow.

For China, Putin’s proposed trilateral gathering presents a unique opportunity. The United States and China have navigated their increasingly contentious relationship by viewing one another as peers with no equals (as the world’s two largest economies, together accounting for more than 40 percent of global output). Deep economic interconnectivity has prevented both states from unilaterally escalating tensions and both Beijing and Washington have a mutual interest in preserving international trade. The presence of Russia, a country that barely trades with the United States and is considerably more confrontational with Washington than Beijing, means that China will have an outlet for the political demands that would be otherwise smothered by the need to preserve economic ties. Xi could even present China’s demands as being a moderate middle-ground between Russia’s maximalist positioning and the United States’ historic approach towards Ukraine and European security. There’s also the reality that this summit would be a 2-vs-1 match between a hapless Donald Trump and two crafty adversarial countries that have individually shown themselves to be capable of manipulating him. Proper coordination between the Chinese and the Russians could lead to unthinkable unilateral concessions from the United States.

Finally, there’s the question of what this meeting would mean for the United States. The second year of Trump’s second term has been defined by his decision to launch a needless, thoughtless, and dangerous war with Iran and his administration’s struggle to handle the ongoing political fall-out from this decision. A trilateral summit would provide a short-lived public relations win for the Trump administration (even if the summit is actively protested against by members of his own party, the intelligence community, and broader American public), at the expense of a whole series of long-term interests. In the best case scenario, Putin and Xi will promise to help Trump exit the Iran war with a whole slew of concessions. Trump will likely surrender America’s positions on Ukraine security aid and NATO’s model of collective security in exchange for a face-saving exit from Iran: reopened shipping through the Strait of Hormuz, perhaps on terms that leave Tehran with leverage over it, paid for with American concessions of its own, including unfrozen Iranian assets and a U.S.-backed fund to rebuild Iran. Telegraphing these possible developments over the next two weeks could provide a cheap diplomatic win before the midterms. This is especially true if the meeting is predicated on a meaningless guarantee from Putin and Xi that Trump will accept at face value and repeat at home - like how China and Russia will ensure that Iran will never get a nuclear weapon or that a new deal has been reached to lower gas prices. The actual agreement that Trump would present to the American people would once again be meaningless and on some level, Russia and China are likely aware of this too. However, we are risking the possibility that cornerstone elements of the post-war order are used by the United States as bargaining chips for empty promises ahead of a disastrous midterm election.

The danger is an understanding between Putin, Trump, and Xi that the world will be partitioned into three distinct spheres. Russia will have direct dominion over Ukraine and de facto control over continental Europe. China will control the Asia-Pacific with Russia ceding influence over Central Asia and America softening its security commitments towards Taiwan, Japan, and Australia. The United States will have de facto control over the Western Hemisphere, having exchanged its place at the forefront of the post-war international order for a militarized sphere of influence over neighboring countries that would otherwise be allies. The final results of this trilateral summit - and the resistance to the vision presented by these three autocrats - may shape the coming conflicts of the 21st century.

That resistance has to start now, before Shenzhen. Congress should demand to know in advance and in public what the administration intends to put on the table and make it clear that commitments to Ukraine, NATO, and our Pacific allies are not Trump’s to trade away in a side meeting. Europe, Japan, and Australia should coordinate before November rather than learn the terms afterward. And no one should accept a settlement on Ukraine negotiated without Ukraine. Yalta taught us what happens when great powers decide the fate of smaller nations behind closed doors. We should not need to learn that lesson twice.

On October 14, Ukraine faced another night of Russian ballistic missile attacks without the reliable advance warning it had come to expect from the United States. Around the same time, Ukrainian forces discovered that their Starlink and Starshield connections had been restricted. Drones lost connectivity, missions were disrupted, and Ukraine is left more exposed to future air attacks.

Elon Musk offered an explanation that should concern every American ally and any American trading partner dependent on U.S. technology and industrial products. Decisions about the use of Starshield, he wrote, are made by the U.S. military and, ultimately, the president. The White House characterized the disruption as a glitch, while Ukrainian officials questioned whether it was deliberate. Recent reporting has Musk proposing to Trump restrictions on Starshield services. While the precise chain of responsibility remains disputed, the strategic implications could end up being disastrous.

Governments around the world are seeing a demonstration of what happens when a government and a critical technology provider collude to restrict critical service to a country. Trump’s and Musk’s petulance, vindictiveness, and transactional ego-driven self-service will have real economic and geo-political consequences.

On the National Security Council, I saw this problem from the other side.

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The warning we gave Europe about Huawei

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He blames the victim, inflates the bill, and invents the polls.

Trump’s approach towards Russia and Ukraine during his first term set the stage for the 2022 invasion. His decision to prioritize his own political interests over national security undermined American democracy, turned security aid to Ukraine in a political scandal, and ultimately encouraged the full-scale war.

Trump’s rant deserves a line-by-line answer because nearly every sentence in it is false. His narrative builds a story Moscow that would gladly sign: that Ukraine started a war it can’t win, swindled America into paying for it, and is run by an unpopular dictator. Each piece fails on the facts.

Here’s the record,

Dear readers,

Tomorrow I will be broadcasting on Substack Live at 2pm ET with Representative Pat Ryan (NY-18) and candidate Cait Conley (NY-17). With the final weeks of the midterms upon us, I’ll be looking forward to two great conversations about the issues that New York voters care about.

Be sure to subscribe and tune in via the Substack app at 2pm ET - you won’t want to miss this!

Recent reporting suggests that the U.S. government has potentially suspended sharing intelligence with Ukraine. This development comes in the wake of an ongoing diplomatic row triggered by Donald Trump’s demand that Kyiv cease targeting Russian refineries and energy infrastructure. U.S. officials stationed in Kyiv and European capitals worked the phones through the weekend, warning our allies that Washington would cut-off intelligence and block usage of the “PURL” mechanism (a legal agreement that allows European states to purchase weapons from the United States for Ukraine) unless Kyiv stopped striking Russian refineries. The United States has not confirmed a suspension of intel sharing and the European Commission reports that there is no known disruption of American intelligence sharing with Ukraine. Zelenskyy claims that Ukraine did not receive routine early warning notifications of a recent Russian missile attack on Kyiv that left 600,000 without power overnight. Furthermore, there are reports that Starlink connections were limited for Ukrainian systems operating in excess of 100 mph - a limitation which has already compromised missions and movements in Eastern Ukraine.

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After receiving pushback from Ukrainian President Zelenskyy, Trump stated that “it’s time for Ukraine to get a new president.” Musk joined in the president’s rhetoric and called for a new Ukrainian president. Next, the White House announced a truce between Ukraine and Russia covering refineries and energy infrastructure - only for neither side to acknowledge the existence of this agreement. Russia struck a Ukrainian power plant just hours after Trump’s supposed truce was announced.

This is a mess. The chaos of the Trump administration’s Russia-Ukraine policy only advances the interest of our enemies. However, beyond the bluster and spectacle of the diesel agreement over past 48 hours, the Trump administration has quietly handed a significant win to the Russians by failing to act on the arrest of Mikhail Zvinchuk, operator of the “Rybar” misinformation network, in Montenegro. Zvinchuk previously faced a $10 million bounty by the State Department for his role in election interference. A major player in Russia’s misinformation operations was arrested in a NATO country just days before the midterm elections - yet the Trump administration failed to take any meaningful actions before he was expelled and sent back to Russia. Alarmingly, a post from the Rybar network prior to Zvinchuk’s arrest suggests that America’s competitive Senate races may be targeted by misinformation operations in the coming midterms.

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Today, President Trump announced on Truth Social that following a “highly successful” call with Vladimir Putin, Russia would supply hundreds of thousands of tons of diesel immediately with additional shipments to follow. Trump promised that prices would come down “in record numbers, and fast.” This announcement raises a more important question than whether or not prices will fall: what is the United States giving up to make this happen?

Let’s start with the Strait of Hormuz. Trump claims the United States has “TOTAL CONTROL” of the strait yet he is turning to Putin for energy relief. If the strait is secure and energy can move freely, why is Russian diesel necessary? If disruptions are serious enough to require Russian supplies, then the administration’s claims of success deserve scrutiny. Either way, a deal with Moscow is no substitute for a coherent energy strategy.

The bigger problem is what this means for Russia. Energy exports help sustain the Russian economy and finance Putin’s war against Ukraine. At a time when Washington should be increasing pressure on Moscow, Trump is presenting a new commercial arrangement with Putin as an American victory. Three weeks ago Trump signed the Lindsey Graham Russia Sanctions bill as a testament to Graham’s commitment to stopping Putin’s war-machine, and now Trump is announcing we’re importing fuel from Russia. The administration has shown itself to be scattered and uncoordinated in its own priorities and has created opportunities for our adversaries to exploit.

Consider the double standard. Ukrainian strikes have damaged Russian refineries, degrading infrastructure that supports the Kremlin’s war effort. The administration has pressed Kyiv to limit attacks on Russia’s energy sector. Yet Russia continues to strike Ukraine’s power plants and energy infrastructure, leaving civilians vulnerable to the cold and the dark. Ukraine is being asked to constrain its ability to strike back while Russia stands to benefit from new opportunities to sell its fuel. Additionally, this development creates a double standard for the United States’ relationship with Europe: Washington spent years pushing for Europe to pivot away from Russian energy imports and managed to coordinate a continent-wide reduction in Russian energy consumption, only to unilaterally cut a deal with Putin for diesel.

This is a failure to understand leverage. Sanctions, high interest rates, labor shortages, and Ukrainian strikes have all put real pressure on Russia’s economy. That pressure should be used to secure meaningful concessions and an end to the war. Instead, Trump appears prepared to ease that pressure without securing a ceasefire, a Russian withdrawal, or a halt to attacks on Ukraine’s energy infrastructure. What, exactly, has Putin conceded in return? Trump’s statement included the phrase “it must be understood that Iran will never have a nuclear weapon” - is Russia the guarantor of this? Are we turning to intermediaries like Moscow after failing to win the war in Iran?

Americans deserve relief from high fuel prices. Farmers, ranchers and truckers are facing real costs, and the administration has a responsibility to address them. But energy policy cannot be judged by a headline or a promise. We must also consider the strategic cost.

Putin is making no concessions regarding the Ukraine war, but Russia is getting economic relief, and the United States gets merely a promise of lower prices. That is a poor exchange. This also creates a situation where further Ukrainian attacks on Russian energy infrastructure could create a hard break in relations between Kyiv and Washington, a once-unthinkable development considering the United States’ historic support for Ukraine following the 2022 invasion. America should use its economic and diplomatic leverage to end Russia’s war, not give Putin another opportunity to benefit from it. Lower energy prices are a legitimate goal. Helping sustain the economy that finances Russia’s war is not the way to achieve it.

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The Ukrainian military is in the midst of an ongoing counteroffensive known as “Operation Vivaldi” in Donetsk Oblast. At the time of writing, the Ukrainian military reports that Vivaldi has led to the reclamation of at least 176 square kilometers (~68 square miles) of territory. While this figure may seem limited compared to the vast geography of Ukraine and the length of the line of contact between Russian and Ukrainian forces, it should be noted that this reclaimed territory is located within a region known as the “fortress belt.” This section of Donetsk is home to a dense string of industrial sites and cities (most of which are now depopulated) that have seen some of the most intense fighting since the start of the 2022 invasion. Every mile of ground gained through Vivaldi is another degree of relief from Russia’s multi-year siege of the fortress belt.

Given that this is an ongoing operation, we can expect that Vivaldi may yield additional gains for the Ukrainian military in the coming weeks - Russian forces may be pushed even further back or another Ukrainian salient may appear elsewhere along the line of contact. Nonetheless, I wanted to provide my reflection on the tactical and strategic aspects of Vivaldi and what role this operation plays in Ukrainian Victory

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Readers,

It’s been about a month since I relaunched my Substack and I hope you are enjoying it as much as I am! There is certainly no shortage of national security and geopolitical news to discuss.

Russia is once again at the center of some of the most consequential stories in the world. The war in Ukraine is entering another dangerous phase as winter approaches. Russia is intensifying its attacks on Ukrainian cities and critical infrastructure. At the same time, Ukraine has been striking deeper into Russia and putting increasing pressure on its energy sector - so much so, in fact, that Trump administration officials have attempted to blame Ukraine for the high fuel prices around the world. Putin is once again rattling the nuclear saber and there are reports that Gen. Sergei Surovikin, the ‘General Armageddon’ who ran Russia’s first winter campaign against Ukraine’s power grid, may be coming back from exile.

That being said, my most immediate concern is a bizarre and potentially serious story developing in Siberia, where an employee of an anti-plague research institute died after developing a rapidly progressing pneumonia of unknown origin. Russian authorities say testing has not identified plague, but quarantines and other precautions have been put in place. The bottom line upfront with Russia is that Moscow has a long record of concealing incidents like this, from Sverdlovsk to Chernobyl. This history gives us a reason for real skepticism about the official account. It’s pretty clear something is going on, but we don’t know what.

This is a time when expertise matters and, unfortunately, we have very few subject matter experts left in government service. One of the reasons I started Why It Matters was because I wanted a place where we could do more than react to headlines. As you know, I spent more than two decades working on national security, much of it focused on Russia and the former Soviet Union. One of the things I have found most rewarding since leaving government is helping people understand not only what is happening, why it matters, what to watch next, and how events fit into the larger picture. This requires deliberate conversations as opposed to five minute media hits.

This week, we’re going to do a lot of that live.

I’ll be continuing my series of Substack live election events with conversations with Brigadier General (Ret.) Leela Gray, who is running for Congress here in Florida, and Congressman Jason Crow of Colorado this Thursday, October 8th at 3pm ET.

There will also be an event with yet another Vindman!

My sister-in-law, Dr. Cindy Vindman, is a microbiologist with expertise in biosecurity, and she will join me for a special live conversation tomorrow, October 6th at 4pm about what’s happening in Siberia. What do we actually know? What don’t we know? What would scientists and public-health officials be looking for right now? How should we think about information coming from Russia, particularly when an incident involves a facility that works with dangerous pathogens?

This is exactly what I want Why It Matters to be: serious conversations with experts who know what they’re talking about, without requiring you to have a graduate degree in a specific field in order to follow along. I want to inform, not sensationalize.

And because this is going to be such a big week, I want to open the doors a little wider to grow our community. For the next 48 hours—through Wednesday night—paid subscriptions are $6 a month or $60 a year, down from $7 and $70.

Use this link to access this special discount pricing. This link for discounted membership is only available through this post, so be sure to join!

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Paid subscriptions support the work I’m doing here and give me the ability to spend more time digging into these issues, bringing in knowledgeable guests, and having conversations that go deeper than the television-news version of events. There is an enormous amount of noise in our information environment. Understanding Why it Matters is even more important.

I hope you’ll join us this week.

Over the past few weeks several significant developments have unfolded in the War in Ukraine. The Ukrainian military launched “Operation Vivaldi,” a counteroffensive which has successfully pushed Russia’s forces back from the string of cities known as the “fortress belt” along the line of contact in Donetsk. Vivaldi is the kind of a well-planned and well-resourced operation that Ukraine needs to be able to execute in order to overcome the Russian military’s posturing and liberate territory in Eastern Ukraine. Parallel to this, Russia has initiated its winter bombing campaign aimed at civilian infrastructure targets in Ukraine. In the midst of Russia’s losses on the battlefield and increasing attacks on civilian targets, the Trump administration has proposed to ease sanctions on Russia - a surreal development amidst a potential turning point in Ukraine’s defense.

Two other events in the past weeks have received less attention but further illuminate Putin’s Russia for what it really is: elections in Russia’s Duma (parliamentary/legislative branch of government) and a plague outbreak in Irkutsk, Central Siberia - a city I stepped foot in back in 2009.

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The Iraq war will always be deeply personal to me. During my deployment I lost friends, was wounded by an IED, and watched a generation of our military live through a war in the Middle East that brought neither peace nor stability. This past memorial day I delivered a campaign speech in Tampa to hundreds of attendees, remembering and celebrating those that gave their last measure of devotion in service to our nation.

The United States officially withdrew its remaining personnel from Iraq this past week. This marks the second time that we’ve exited the country (our first absence lasted just a few short years before forces were redeployed to fight ISIL in 2015). What should have been seen as the closing of a chapter of our military’s history didn’t register with Americans or the national security community. This is because our withdrawal comes as our military is overextended in another war with Iran. It hurts to see our country repeat the same mistakes year after year, administration after administration.

As I noted in my September 11th reflection, 9/11 pierced the veil of America’s invulnerability. We no longer saw ourselves as insulated from war and distant conflict by two oceans. A terrorist attack at the heart of American society demanded a response and our mission to Afghanistan was a just cause to drive out and punish Al Qaeda. Iraq was an entirely different story.

The 2003 invasion of Iraq was a war of choice. A generous read on the decision-making at the time was that we were preventing a rogue state from acquiring WMDs - our intel was shaky but we were acting on the urgency of keeping devastating weapons out of the hands of a belligerent tyrant. The less-charitable reality was that the decision to invade was in pursuit of a combination of objectives, including the need to punish Saddam by finishing the war that Bush-senior had started. That war triggered decades of regional conflict, including empowering Iran by removing the threat of another Iran-Iraq war. We’ve spent decades attempting to control the fallout from our actions.

The Iran War is another needless, costly war of choice. The Trump administration’s justification for this conflict - that Iran was on the verge of obtaining a nuclear weapon - is even more shaky than the WMD pretext for Iraq. In the case of Iraq, the wounds of 9/11 were fresh, the insecurity real, and the legal basis (an act of Congress providing the basis for U.S. military action) was extant. Iran was not on the cusp of nuclear breakout because Operation Midnight Hammer severely degraded Iran’s nuclear program - even if the exact claims of damage were exaggerated by the Trump administration.

Every US President since at least Nixon has attempted to stabilize the Middle East and failed. Were any lessons learned over the past 20 years on wars of choice? Not only have we failed to define objectives and mission scope, we’ve managed to burn bridges with allies and create a self-induced global energy crisis.

Time will show the final cost of our war in Iran.

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Dear Readers,

Tomorrow I will be broadcasting on Substack Live with Senator Tammy Duckworth and Democratic Candidate Jessica Killin (CO-05). Senator Duckworth is a veteran of the United States National Guard and has represented Illinois in the Senate since 2017. Jessica Killin is an Army veteran and Democratic nominee for Colorado’s 5th congressional district.

With the midterms just weeks away, I’m looking forward to having a discussion with these two veterans on the issues their constituents care about and the national security challenges facing the United States. Tune in to Substack Live via the Substack App and donate to Jessica Killin’s campaign via ActBlue here:

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-Alex Vindman

Why It Matters publishes guest essays providing thoughtful analysis of critical issues. Justin Tomczyk is a former Eastern Europe Subject Matter Expert at the event detection firm Dataminr. He worked as my research assistant for “The Folly of Realism”, Policy and Operations Lead for my campaign, and is currently my Chief of Staff.

In her proposal for a new “Alliance of the Future”, EU President Ursula von der Leyen outlined a vision for “a common prosperity and economic security space” between Canada and the European Union. This proposal would include Canada becoming an “Associate Member” of the EU. Canadian Prime Minister Mark Carney welcomed this proposal and called for closer cooperation between Canada and the European Union while referencing the challenges of the ongoing “Geopolitical Rupture” in the world. President Trump called the plan “laughable” and threatened additional tariffs on Europe.

I’ve spent several years studying the expansion of the European Union and the legal process of European integration (including reading the European Federalist Papers many summers ago…). Considering that this field is grounded in analyzing treaty text and legal processes, things tend to move at a glacial pace and major developments are broadcasted well in advance. This makes the announcement of Canada’s potential “Associate Membership” a unique surprise.

First and foremost, this proposal would represent the first westward expansion of the EU. EU membership forecasts are mostly focused on the Western Balkans, the South Caucasus, and countries like Ukraine and Moldova that are located along the eastern periphery of the union - I don’t think Canada was on anyone’s bingo card for “next member of the European Union”.

Additionally, enlargement of the European Union often involves the political transformation of a prospective member. In the 1990s many former communist countries used the goal of future membership in the European Union as a vehicle for implementing free market and democratization reforms. In recent years, emerging democracies like Ukraine and Armenia have tied EU membership aspirations to anti-corruption efforts. As an already democratic society with a free market economy, it’s unclear what political changes would come with Canada’s new partnership with the European Union.

There’s also the question of what exactly President von der Leyen meant when she described Canada as a potential “Associate Member”. The European Union has three labels used for partner countries: “member states” , “candidates”, and “associates”. Member states are part of the “Single Common Market”, a continent-wide free trade area and shared customs code that is designed to facilitate the free movement of goods, people, labor, and services between members (essentially a European analog to the United States’ Commerce Clause). Member states also participate in the union’s political decision making processes and adhere to all laws, standards, and regulations set by supranational authorities like the European Commission.

“Candidate” countries have been officially recognized by the EU as potential future members. They are expected to comply with all the rules and regulations of the EU but do not participate in any of the EU’s decision-making processes. Candidacy is not a guarantee of membership and the accession process is a long, complicated process that takes years (if not decades) to complete. Membership prospects can be frozen due to political considerations, derailed by democratic backsliding, or outright vetoed by a single EU member during a diplomatic row with a candidate country.

“Associate” of the European Union is a tricky label. Officially, any country that holds an “association agreement” is an associate of the European. Association agreements typically include partial integration with the Single Common Market and some form of alignment with the EU’s political systems. However, unlike candidate countries, EU Associates are not expected to continuously integrate themselves into the political and economic systems of the European Union. For instance, Norway and Iceland are two associates of the European Union that are politically aligned with the EU and nearly fully integrated into the Single Common Market. However, both countries have avoided full membership in the EU in order to preserve national control over critical industries (fishing for Iceland and energy extraction for Norway). For these two states, the economic benefit of retaining national control over these industries outweighs the lack of inclusion in the EU’s political decision making process.

With all this in mind, we must turn our attention back to Canada: what exactly can we expect from an “Associate Member”? There’s nothing stopping Canada and the European Union from allowing the free movement of people, goods, and services between one-another - although the literal ocean between both parties raises the question of just how practical this sort of agreement would be. Participation in the Single Common Market is technically possible, however this would likely be an elaboration of already existing free trade agreements between Canada and the EU.

I would argue that the most important element of Canada’s “Associate Membership” with the European Union relates to security and defense.

More specifically, we should recognize that Associate Membership opens the door for Canada’s inclusion in the EU’s collective security framework. The European Union has two collective defense clauses that are similar to NATO’s Article 5. Article 42.7 of the Treaty of Lisbon, known as the “Mutual Defense Clause”, calls for members of the European Union to come to the aid of another member in the event of an armed attack. Additionally, Article 222 of the Treaty of the Functioning of the European Union requires EU members to jointly coordinate their responses to events like a terror attack or natural disaster.

The European Union’s defense policy portfolio includes much more than just mutual security clauses. The Common Security and Defence Policy (CSDP) is a collection of defense projects, multinational deployments, and union-wide defense plans that include the operation of rapid-response EU Battlegroups and the coordination of weapons manufacturing and procurement. Canada has already seen success working with the EU’s CSDP through its participation in the European Union Monitoring Mission in Armenia - it’s entirely possible that Canadian personnel join an EU peacekeeping mission or deployment to Ukraine or Taiwan.

A Divided Atlantic?

NATO and the EU have historically been considered complimentary pillars of the Transatlantic alliance. However, with the second Trump administration’s adversarial approach towards relations with the European Union and expansionist rhetoric towards Canada and Greenland, many allies are reexamining whether or not the United States will actually uphold NATO’s security guarantees in a crisis. Denmark, a NATO member and ally of the United States, has already directed counterintelligence operations towards American citizens in Greenland suspected of conducting influence operations.

Canada’s participation in the EU’s “Alliance for the Future” may signal the first major divide in the Transatlantic partnership. In the short term, Brussels and Ottawa may act as a united front against the Trump administration’s erratic tariff policies and coordinate retaliatory economic measures. With the dysfunction seen in the Five Eyes intelligence sharing alliance under FBI Director Kash Patel, Canada may view Europe as a preferred partner for threat forecasting and counterterrorism coordination. In the long-run, Canada’s alignment with the European Union may present larger, structural challenges for the United States. Canadian adoption of EU regulations for food safety may limit the United States’ ability to negotiate bilateral trade agreements with Canada (historically, disparities between American and European health standards have been a major hurdle to EU-US trade deals - disagreement over “Chlorinated Chicken” is a well known example). Canada may join Europe’s strategy for digital autonomy and move critical systems away from American networks. Additionally, Canadian-European defense alignment presents the possibility that Canada chooses European arms and aircraft as an alternative to American defense tech. The economic and political impacts of above are heightened when we consider that this would be a needless, self-induced schism with one of two countries directly bordering the United States.

There are several retaliatory measures that Trump administration could deploy in response to this proposed alliance. Having already levied tariffs against Canadian and European goods, the second Trump administration could raise tariff rates even further or declare a full ban on imports from either Canada or the EU. Trump could also unilaterally suspend defense cooperation with Canada or limit the ability of American and Canadian citizens to travel to either country as a punitive measure. There’s also the possibility that the Trump administration sabotages the ratification of Canada’s “Associate Membership” by either securing a veto vote from a single EU member or mobilizing Quebec’s autonomous government against the ratification process (recent reporting suggests that the Trump administration has already attempted to use Quebecois separatism against Carney’s government).

Looking beyond the Trump administration’s potential reactions to this treaty, we must also consider how this alliance could benefit the United States in a future administration. If Brussels and Ottawa are successful in securing Canada’s Associate Membership and the “Alliance of the Future” delivers on the vision for common prosperity and economic security, this new union may become a true successor to NATO. By fusing political, economic, and security cooperation into one structure, the Alliance of the Future would supersede NATO’s original focus and command enough military and economic weight to match the rising challenge of China. By signing a bilateral treaty with this alliance, the United States may open new avenues of cooperation in emerging industries that were not available through previous trade agreements. The treaty structure used for Canada’s Associate Membership could be recreated for a future agreement between Ukraine and the EU - or Ukraine could be included as the third member of the alliance. Membership in the Alliance of the Future could even be extended to strategic partners like Japan, Taiwan, and Australia that fall outside the geographic area associated with NATO and the EU.

Time will show as to what becomes of Canada’s proposed EU Associate Membership and if the “Alliance of the Future” materializes as an actual political union. What is clear, however, is that the United States’ inward retreat from the global stage has created a power vacuum that our enemies and allies are desperate to fill. In a time of rising authoritarian powers, the Alliance of the Future may emerge as a counterweight that is centered on defending democracy across the globe.

We see the world with the same eyes: from AI to climate change, from the Arctic to geopolitics. And we have stood together: on Ukraine, on defence, on raw materials and on supply chains. But above all, dear Mark, Europe and Canada believe in democracy. We believe that power does not belong to the strongest, the richest or the loudest – but to all of us. That democracies have the freedom to choose with whom to work.

-EU President Ursula von der Leyen

Why It Matters publishes guest essays providing thoughtful analysis of critical issues. Casey Michel is the author of “United States of Oligarchy”

It’s hardly surprising that Donald Trump and his family are considered the most corrupt occupants the White House has ever seen. Perhaps the only surprise remaining is that, especially for those of us who cover and analyze corruption for a living, there are still moments that can shock us.

Such was the case last week, when ProPublica revealed that a Kremlin-linked figure named Umar Kremlov secretly paid for much of Donald Trump Jr.’s wedding weekend earlier this year. As ProPublica discovered, Kremlov provided Trump Jr. and his wife with a “gift” of hundreds of thousands of dollars, all to help celebrate their nuptials. It was, as Trump Jr.’s wife described it, an offer from a “dear friend,” and one they simply couldn’t turn down.

If only that were so. As those who follow the world of both corruption and Russian malign influence know, Kremlov is hardly an apolitical actor. He is instead a Russian businessman who is remarkably close to the Kremlin. Indeed, describing him as a businessman is perhaps too generous. Not only was Kremlov previously convicted of multiple crimes, ranging from extortion to battery, but he has been specifically sanctioned by the Ukrainian government for his relationship Vladimir Putin. Kremlev owes much (if not all) of his wealth to remaining in the Kremlin’s good graces, and to retaining his relationship with Russia’s leadership – a fact that the Kremlin knows well, and is eager to take advantage of.

“Kremlev is a very well-known figure – and a particularly vivid representative of a new generation of Putin-era oligarchs,” Russian journalist Mikhail Zygar noted. “He is a product of one of the most important transformations of Putin’s Russia: the emergence of businessmen whose wealth depends not primarily on privatization, natural resources or entrepreneurial talent, but on access to the security services and, ultimately, to Putin himself.” In other words, Kremlov is no anodyne businessman. He is, instead, something closer to a gangster who has ascended the ranks of the Kremlin’s power structures – and who now acts as a proxy for Russian interests, including the cultivation of members of the Trump family.

It’s unclear how much Trump Jr. or his wife knew about Kremlev’s background, his relationship with Putin, or what he and the Kremlin ultimately wanted. But the reality is now inescapable: a Russian gangster and Kremlin proxy successfully gave a six-figure gift to the son of the sitting US president – all of which would have remained secret had it not been for pioneering journalists at ProPublica.

There are still a raft of questions swirling the entire affair. How much did the rest of the Trump family know about the payment? (Both the president and Eric Trump have denied any knowledge of Kremlov or the payment, effectively throwing Trump Jr. under the bus.) Will Trump Jr. actually return the payment, as his father said? And was the payment about more than simply leverage? Were Kremlev and his associates happy to simply have Trump Jr. indebted to them, or did they gain any compromising material at the wedding itself?

These are all questions we won’t have answers to as long as Republicans control both the presidency and Congress. But should Democrats regain the House (and potentially the Senate), they now have that much more reason to set up a select committee to specifically investigate all the corruption drowning the Trump family – and to finally unearth what the Kremlin was trying to do in cultivating Trump Jr. and others at the wedding.

After all, the entire affair hardly exists in a vacuum. This is but the latest in a long litany of corrupt or questionable actions involving the Trump family, both before and during Trump’s presidency. Many of those involve Trump Jr. himself, from his work at the crypto firm World Liberty Financial, which secretly counted the foreign regime in the United Arab Emirates as one of its primary backers. But others within the family have been more than happy to profiteer from the presidency, including Eric Trump’s role in both crypto payment schemes and favorable defense contracts. And there is, of course, Jared Kushner and myriad foreign clients, all of whom have plowed billions of dollars into Kushner’s firm – and all while the Kremlin continues to dangle contracts supposedly worth trillions of dollars to Kushner and his contacts.

It is all far beyond anything we’ve ever seen prior, and points directly to how all of these kinds of links – clandestine payments, secret investments, pay-to-play access from foreign regimes around the world – distorts American foreign policy, and even sells American national security to the highest bidder. A Russian gangster secretly paying for the son of a sitting president may be the most bizarre, but it fits a pattern we’ve seen emerge in recent years, especially involving the Trump family.

There’s a name for all of this: “strategic corruption.” First popularized in 2020, this describes a kind of covert payment scheme or structure that goes beyond traditional corruption. Instead, this is a generally state-led effort to use corruption – including bribes, crypto payments, and, yes, gifts – to obtain the kinds of policy outcomes that states want. Nor do these kinds of corrupt payments have to necessarily involve a government official. Instead, they can often involve proxies and connections for the regimes in question, from oligarchs to gangsters to family members. All of it is generally hidden in backroom deals, and generally concealed by anonymous or under-the-table payments. But it all results in policy decision being sold to the highest bidder, wherever they are.

It’s unclear what the primary policy outcome Kremlev and his handlers in the Kremlin wanted. Maybe it was sanctions relief. Maybe it was the further pullback of American support for Ukraine. Maybe it was something else entirely. But the specific ask is almost beside the point. The reality is that, because of an apparent combination of both ignorance and bottomless greed, Trump Jr. and his wife opened their wedding to a man who is little more than a foot-soldier for the Kremlin – and opened up American policy-making that much more to a regime who wants to destabilize the US, destroy American interests, and roll back American influence. The Kremlin, and corrupt actors around the world, couldn’t have asked for more.