In one of your interviews you said that you visit Ukraine three times a year and spend a few weeks there. What exactly do you do here?
I work for the American think tank Foundation for Defense of Democracies. We support democracies under pressure, such as Taiwan, South Korea, Ukraine, Israel — countries that oppose Russia, China, North Korea, Iran, that is, the axis of evil.
I run a couple programs. One of them is the Russia program, where we push back against Russian authoritarianism. As part of this program, we cooperate with the Ukraine Freedom Fund and conduct courses for the Ukrainian military on combat planning. These courses are approved by the Ukrainian General Staff. This initiative was launched at the end of 2022 by Marine Corps General Bill Mullin.
And when did you first come to Ukraine?
I first came here in 2023 as part of this program. But I was actually here as a boy. My father was stationed in Moscow at the embassy. So I lived. I came to Kyiv two or three times, like pre Chornobyl. So 1983, 84, 82, 83 timeframe.
When I was with the US European Command, I came four or five more times. And Senator McCain sent me here twice to help with cyber issues. So Iʼve probably been here 15 or 20 times in total.
Montgomery is invited to various venues in Ukraine to talk about national security. In particular, to the National University of Kyiv Polytechnic Institute for a talk with scientists, professors, military commanders, and representatives of the General Staff of the Armed Forces of Ukraine.
You have been observing the Ukrainian army for a very long time and can you tell how it has changed since 2022. Are these changes positive or negative?
The Ukrainian army has shown very good results. Are there things that can be improved? Absolutely. On the other hand, the Ukrainian army does things that no one else in the world does, except, perhaps, the Russian army. We see rapid adaptation to new defense technologies and processes in war.
In particular, this applies to drones, but not only. The new generations of drone technology every two, three, four months. These are fantastical things that would not have happened in the United had not happened in the United States. However, the big challenge is the resilience of the armed military and the resilience of the society.
Letʼs talk about how to become better. During the first year of the full-scale invasion, the Ukrainian army showed very good results: we knocked out the Russians from the Kyiv, Chernihiv, and Sumy regions, and returned some territories in the Kharkiv and Kherson regions. But then the Ukrainian army lost the initiative, and many experts believe that this happened after the counteroffensive. Recently, former commander-in-chief Valerii Zaluzhnyy stated that the counteroffensive failed because several brigades that were supposed to operate in the Kherson region were taken to another front line. Could three brigades have changed the situation and why, in your opinion, did the counteroffensive fail?
The initial successes in 2022-2023 were partly the result of good Ukrainian planning, and partly of Russian blunders. When the counteroffensive began, the Russian army was much better prepared. Then they revised their approaches, involved a lot of people. They started to massively involve prisoners, Prigozhinʼs PMC "Wagner" fought effectively.
You know, I would almost always say that if an offensive had high end, ready to go, brigades ready, could it be more successful? Yes. But I canʼt tell you what the collateral damage of that decision is by pulling them from someplace else.
Whatʼs that impact? Is someplace else so vulnerable that thereʼs a counterattack by the Russians there? I donʼt know. So itʼs very, we call that in America “Monday morning quarterbacking”. You know, looking at Sundayʼs game and saying, hereʼs what I would have done different.
But analysis is important to avoid repeating mistakes in the future.
Yes. And it is also necessary to study the successes and problems of the Kursk operation. I would say historically I am not aware that the Soviet system did that sort of self analysis. And therefore the militaries that grew up in a Soviet system are not predisposed to do effective lessons learned.
So a big lesson of, you know, working with the United States in general is the idea of kind of brutal assessments of what happened. But even despite this system of analysis, the American army still made serious mistakes. That is, it does not protect against failure, but it increases the chances of success.
Speaking of the Ukrainian army, in your opinion, does the military command have clearly defined war goals and a strategy for achieving them? And how do you assess the current strategy — its advantages and disadvantages?
Yes, there is a strategic approach. But no strategy will look guaranteed to be successful when the enemy is much stronger and larger, and resources are unpredictable due to the US position on the supply of spare parts, ammunition, or intelligence support.
Therefore, Ukrainian military strategists must be very careful. They cannot guarantee all the expected resources. Under such conditions, the strategy will likely be more conservative, less risky than one would like. And from the outside, this may look like an overly passive or defensive approach.
And speaking of the mistakes made by the command, can you name them?
Iʼm not sure that these are mistakes. So listen, I would probably things I would do different. So first of all, this has to be framed by an assessment that the Ukrainian army is doing a very good job and their commanders are doing a good job.
If we talk about changes at the nuance level, one of them is how aggressively we use the air component, the air force. We call the word “apportionment”. Itʼs the what percentage of their effort is offense.
The United States Air Force it is historically when theyʼre fighting in a joint environment. Myself as a joint commander, I would tell the Air Force, your apportionment is much more aggressive — 70% offense, 30% defense, maybe 80, 20. Now thatʼs not appropriate for the Ukrainian.
lryna Vlasiuk / «Бабель»
Yes, because we donʼt have enough planes that could do it...
Such exactly, but it would still be like 20% offense or 10% offense, 80% defense, 90% defense. I think itʼs even less now. So I would allocate a little more to offense.
But that requires the right weapons systems — and some of them are available, like the GBU-39. You need enough of the right aircraft — and some weapons are coming, like the ERAM. These assets can be used to attack and push the Russians further away — increase the zone of impact from 90-100 kilometers to 400 kilometers.
Now the Russians will struggle, but you have to have sufficient number of weapons so the United States has to deliver them, Europe has to buy them, Ukraine has to use them, and then you have to have a commander that apportions forces properly.
Now another part is that the army has to work with the air Force. I would say while the Ukrainian army is impressive and the Ukrainian navy and air force have done their job, I donʼt see the same kind of like joint integration that I would see in the United States or say United Kingdom operation. But thatʼs because we spent most of our, you know, weʼve spent 70 years building that.
So, you know, Ukraine is very quickly trying to get there, but I hope they get there soon.
Speaking of weapons, will the US sell them?
The weapons I mentioned have already been sold. Iʼve seen public information about over 1 100 units. They will arrive over the next year, but then maybe buy more and more.
Ukraine has been asking for “Tomahawks” for a long time, because these missiles hit even further.
I love “Tomahawks” and have launched them a lot. The enemy didn’t like them. They are very good weapons, but the number of these missiles is limited. Just like the number of ground-based launchers.
And I’m not 100% sure whether the “Tomahawks” that Ukraine will receive will have all the survivability characteristics that allow American Tomahawks to reach their targets. Maybe it will, maybe it wonʼt. And they are expensive compared to other means of destruction. The President [Trump] said “maybe”, but that was a long time ago, and I haven’t seen any concrete steps.
I certainly defer to President Zelensky. You know, itʼs his right to say what is his favorite weapon or most desired weapon, and thatʼs okay. But I would probably insist on doubling the number of ERAMs. The most important thing is that the US supplies offensive munitions, and which ones — Tomahawk, ATACMS, ERAM — is not so important.
We want you to win.
Do you think the Trump administration wants us to win?
Well, I want you to win. Iʼm disappointed in President Trumpʼs approach. Very disappointed in Steve Witkoff. He is completely unqualified to do this job, and and he demonstrates it every meeting with Putin. We continue to treat Putin as if he is not a war criminal who killed, who jailed and then executed his opposition Alexander Navalny.
Well, he has also started aggression against another country.
Yes, he started the war. And when Witkoff says this is silly, that we canʼt get peace. Itʼs not silly for Ukraine. Ukraine was attacked. Itʼs as if Witkoff is unaware how the war started. I think he might be unaware just how the war started. And a complete misreading of how Putin responds. He does not respond to weakness. He only bends his knee to strength. Heʼll never. He doesnʼt look for consensus. He looks to win. So we need to act.
The United States needs to be a better arbitrage. We probably need someone different than Steve Witkoff. And while President Zelensky is not allowed to say that I am and Witkoff is doing. Heʼs not doing America. Heʼs not doing Ukraine justice. Heʼs not doing America justice with his negotiating.
But we have strayed a bit from the topic of long-range strikes. You shouldnʼt focus only on the “Tomahawk”. Your “Flamingos” already fly as far as the “Tomahawk”.
Moreover, your “Flamingos” have a larger warhead, they are more powerful, but less survivable. The “Tomahawk” has a better chance of breaking through. There was a big “Flamingo” strike recently.
Arrival of the “Flamingo” missile in Russian Udmurtia.
Are there any other errors or tips?
I don’t give advice based on mistakes. Our training is based on how the US prepares headquarters for maneuver warfare. We work with corps and brigades. Some headquarters are brilliant, others have little experience.
And interestingly, the quality of the headquarters does not depend on whether the officer served before 2014. New officers who came to the army after 2014 are just as effective, and sometimes better.
At the beginning of the Ukrainian armyʼs transition to the corps system, you praised this decision. But now the units that make up the corps are scattered across the front lines in the lanes of other corps. In addition, we often see manual control, sometimes commanders from Kyiv give orders directly to brigades or battalions, destroying the structure. And soldiers are sometimes afraid to immediately report a withdrawal from positions, which complicates maneuver.
Thatʼs a fair question. So what I would say is, and I still am very supportive of the core of the reorganization of the core structures, the reorganization of the operational groups. I think, theyʼre generally organizing themselves properly.
I might use different names for things that the cores look more like divisions to me. But that doesnʼt matter.
But itʼs a fair assessment to say well itʼs not working perfectly everywhere or itʼs not working well everywhere. And thatʼs to be expected. This was not a piece of, you know, magic beans and you put them out and you didnʼt imply that. But you know, you have to. You know, General David Petraeus (famous American general) would say itʼs very hard to build the plane while youʼre flying it. And I think thatʼs whatʼs going on.
Youʼre reorganizing the military in the middle of the largest, most aggressive ground conflict in Europe since World War II. Thereʼs going to be insufficient progress in some areas.
There will be uneven progress. Some corps will become stellar, others will lag behind. And the new structure will not solve the problems, it will not become a magic pill. It is a question of leadership, and it takes time. But the new structure provides better opportunities.
There is also the problem of communication between corps or units within corps.
So look, this is the hardest part of any military organization is how do you maintain you have a chain of command, but you also have to have. Which gives you vertical flow of information. But just have or horizontal flow across the battlefield.
That is PhD war fighting. Thatʼs the highest level of war fighting, is when you could fight horizontally, vertically and joint. If you could do that, youʼre in great shape.
And you were right. People do not want to give bad news to their leaders. But this is not an organizational problem, but a problem of personal interaction. There is something to improve here. And even more difficult is to integrate the plans of the Air Force with the defensive and offensive plans of the ground forces.
That means it needs to be improved.
Thatʼs an area to be improved. And I would say if thereʼs 193 militaries in the world that needs to be improved in like 190, including the Russian.
You said that Ukraine was able to control the Black Sea without a traditional fleet. How do you think the fleet should be developed?
I also said that this was the most successful year for the fleet in the last 20 years, and not a single ship went to sea. In the current situation, when the enemy is equipped with cruise, ballistic, hypersonic missiles and is ready to use them against ships in port, it will be very difficult for Ukraine to maintain medium or large surface ships.
Therefore, I think the best fleet that the Ukrainians could have are a rich mixture of anti ship cruise missiles, whether theyʼre “Neptunes”, “Harpoons”, undersea vessels, I mean unmanned surface vessels, unmanned undersea vessels, you know, across that and then Unmanned aerial vessels, air systems across those.
That is, all those types of weapons that can be launched from land at sea, and all types of reconnaissance to know where your enemy is. And some small ships that can go out and cause damage to the enemy.
The operation of the “Magura” surface drone.
Головне управління розвідки МО України / Telegram
Are you talking about the “Mosquito” fleet?
The “Mosquito” fleet is a very specific system, it is still difficult for me to imagine that such ships would survive a naval battle for more than an hour now. But thanks to the actions of the Ukrainians, Russia can no longer control the sea off the coast of Ukraine, neither in the Black Sea nor in the Azov Sea. Ukraine cannot establish its own control, but it can deprive Russia of control. This is a great victory.
So I think first, continue to win, right? Continue. Continue to know that you are the superior army fighting against just war, against a, you know, authoritarian regime.
So some of itʼs spiritual, emotional, but then, you know, you have to get the right weapon systems. Always be assessing what do I need. Some of them are many. Many of the weapon systems that the Ukrainian army needs today are made by Ukraine. Every year a higher percentage, maybe more than 50%.
This is the main idea — not to depend on other countries.
Then you donʼt have to rely on other people. Clearly identify what you do need. The air defense systems, 155mm ammunition, Patriot, NASAMS, long-range weapons that I mentioned, and intelligence support.
So, number one, be strong. Number two, build as many of your own weapon systems. Number three, have a clear prioritization list, you know, for Europe to buy from the United States to bring to Ukraine and then finally continue to innovate.
So Iʼve talked a little bit about innovation using the Air Force, but thereʼs a lot of innovation that involves your own. The army using its own unmanned, its own drones better, which every three months or come back, I see better tactics, better technology, better operators. Theyʼre amazing. But you have to continue that and it develops. I say a generation is three months. And you have to stay two generations ahead of the Russians.
The fact that you fell behind the Russians in fiber optic drones hit hard. It shouldnʼt be like this.
Itʼs simple to say “stay two generations ahead”. But how to do it?
Well, first have an open chain of command that allows people to come up with ideas. Right. You had that invest in the teams, you know, in the brigade and battalion level organizations. Encourage the technologists, you know, Ukrainian technologists to continue to do defense tech and bring good ideas to the military. Listen to the operators.
Theyʼre doing all these things that many armies do not do. And that way you fold the lessons learned. You know, the operators tell you the lessons learned to the battalion and brigade that makes the weapons and tomorrowʼs weapons better. No other military does that.
lryna Vlasiuk / «Бабель»
Another question about technology. They are currently testing lasers for air defense systems. Do you believe that this will eventually work? Because I understand that it takes a lot of energy, these are massive systems.
These systems have generators. Will it work? Yes. Will the laser work against a ballistic missile in a year or two? No. Against a fast cruise missile? Probably not. Against a hypersonic one — no. But against “Shahed” drones, or “Geran-2” — yes. Against “Geran-3” — maybe. Against “Geran-5” — no.
But the laser that you have two years from now, maybe it is good against them and some of the cruise missiles. And then five years from now it could be good against the ballistic missiles, the cruise missiles. This things are moving faster in Ukraine than anywhere else in the world. So I would not say that for the American navy or American army.
We are five or six years away from a good laser I that could directed energy or four or five years away. Ukraine is one or two. Will you take more risk? Itʼs okay to fail all these things that we donʼt. Our acquisition program is broken. It is being exposed by the war in Ukraine to be broken so we have a chance to fix it.
I want to talk a little bit about the Russian army. How has it changed since 2022?
Some of its weaknesses remain. They, like Ukraine, are not fully integrated and coherent. They have a much larger Air Force than Ukraine, but they are unable to use it effectively.
They still have problems with large-scale maneuvers and logistics. And they have problems with personnel — from the national minorities they used in the war, they have now moved on to prisoners — people from the lower social classes who are effectively forced to go to war. The oligarchs do not send their children there.
But their technology is evolving. What Rubicon is doing in the drone space is in line with what Ukraine is doing. Their people, systems, and processes are getting better, and there are more of them. But they are still led by officers who are not ready to take the initiative and are tied to an outdated training philosophy. The Ukrainian officer corps is better. Not perfect, but better.
There is a belief that the one who has the best technology wins the war. Do you agree?
Partly. I would say that you are more likely to win a war with new technology. But even with the best technology you can lose. The US has lost wars. But without better technology you definitely wonʼt win.
You said that Russia can only be defeated economically, when its economy starts to collapse. The US Congress has been developing a sanctions bill for a year now. That’s a long time. And even if it is passed, it will still be Trump who will decide whether to impose sanctions and what they will be. Is the US capable of imposing really tough sanctions?
So I hold two uncomfortable facts in my head. Or two uncomfortable beliefs, number one, that this war wonʼt end without strong economic pressure against Russia. But number two, Donald Trump is not the person to do that.
So weʼll have to somehow hold out for another two years?
Another two years, three years, maybe. But also, we could be wrong about Russia. It could break on its own through other things. But I do think the number one cost imposition to itʼs economic.
Itʼs the prevention of shadow fleet deliveries to India and China, but also pipeline deliveries to Hungary. Right. And both to Turkey. You know, some fleet, some pipeline. These countries, the primary receivers of Russian oil, are enabling the Russian war machine. Those sales provide the funds that pay for government operations in Russia. And 42 or 44% of government spending is on defense. That is the war effort, and itʼs got to be stopped.
That is how you break, in my mind, that is the way you pressure Putin into a better, into a consensual basis. I still wouldnʼt trust them. I still wouldnʼt be comfortable with the deal.
So it seems we just have to somehow get through these three years...
Itʼs doable. You have to. Ukraine is the strongest societal resilience in the world. Its people are more stubborn and dedicated to doing the right thing than anywhere else in the world. The society is very responsive to the attack.
You mentioned the shadow navy. Why do you think Trump suddenly decided to fight it, despite pandering to Putin in everything?
There is no excuse anymore. Thereʼs nothing he can say, oh, I need a little more time for this. I need to assess that. Thatʼs bullshit. We know who they are. We know which companies take the fuel and make them and flip it and make the money.
Thereʼs no cover, thereʼs no excuse. You know, everything you need to know. The Shadow fleet is real. It is funding the war machine. It needs to be cut off.
Is the way Trump is currently fighting the shadow fleet effective?
No. How are they intercepting now? France a little bit, sometimes the US intercepts some ships. We are making minor changes on the periphery. We are not creating serious economic pressure.
The deal that President Trump just made with India, in which India promised to stop accepting shadow tankers, could help in theory. But my experience with US trade deals is that they are not very consistent or sustainable, there is no enforcement. And my experience with India is that they are not very reliable.
On January 7, 2026, the US seized the “Marinera” tanker, which was part of Russiaʼs shadow fleet and was transporting oil. All crew members were arrested, but Trump later released two Russians.
Getty Images / «Babel'»
What needs to be done to better combat the Shadow Fleet?
Oh, the way you do it is you two pronged attack. One, you seize the Shadow fleet ships, seize the oil in them and sell it for profit. But two is you sanction the specific Chinese and Indian companies receiving it.
So, should the US and its allies do this too?
Yes. Theyʼll join if we go first and we do. India first, China second.
Do you believe Trump will do this?
I mean, Iʼm being honest with you. Do I wish he would do it? Yes. Do I know he would do it? I donʼt know what heʼll do, but I donʼt think he will.
Recently, we see that Russia is betting on ballistic missiles, and drones are mostly a distraction. The protection of Ukrainian cities and Ukrainian infrastructure depends heavily on American “Patriot” missiles. Their stock in Europe has run out, and the US is constantly delaying the transfer of missiles that Ukraine and European countries buy, not ask for for free. What is the reason for such delays?
So the “Patriot” missile batteries, inventories throughout Europe are very low. And Ukraine, itʼs insufficient. But they do get some in either from European countries who give a few more or from the United States when production comes through and some come over.
Look, I think over time, the “Patriot” missiles will defend fewer and fewer targets. You know, it must have a priority and defend the most important, then the next and the next. If “Patriot” inventory was growing, you would defend more. If itʼs shrinking, youʼll defend less.
So temporarily it may be less, but over time, there are many “Patriots” on back-order to come to Ukraine, and then it will get better again with newer missiles, more capable missiles. Actually, I do think it will get worse.
We say in America, it will get worse before it gets better.
And when will it get better?
Years, not months.
Sure, itʼs disappointing...
Iʼm still coming here. Yes, I believe itʼs safe.
In one of your interviews, you explained that the US will reduce its presence in Europe precisely at the expense of units located in Germany and Poland and performing logistical and training functions, in particular, assisting Ukraine...
There are three types of forces in Europe. The permanent live here, what are called Ford Station forces. And those are really critical to NATOʼs war fight, logistics, targeting, ISR, lift, some other things, but, you know, command centers, things like that. Thatʼs 57 000. Then there was about 15 000 to 20 000 in temporary, what are called rotational assignments. Big in Poland, the Baltic States, Romania. Then there was about another 10 to 15 000.
That was even higher before training as part of the training mission for Ukraine. Thatʼs already being drawn down as that training mission is picked up by NATO. So those numbers are already going down.
You said that NATO is taking over the training mission. But recently the media published information about NATO training in Estonia, which showed that 10 Ukrainian drones are capable of destroying two NATO battalions in a day. So maybe the US is losing because none of the armies, except the Ukrainian one, has fresh combat experience?
The “Hedgehog” exercises were very valuable and important. Itʼs very valuable, very important. Lessons learned. One thing Iʼve learned is war is never like the exercise. So air power will be different than it is here.
Thereʼll be other differences, but donʼt let that distract you. This was a significant learning event for NATO. They need to learn how to fight like the Ukrainians fight against Russia, because Russia is learning how to fight in their fight with Ukraine.
So we cannot fall behind on the lessons learned curve. So even if you say, you know, we say donʼt fight the game, you know, I mean, donʼt fight the scenario. It isnʼt perfect, but let it play out. And I think we learned a lot and we learned a lot about how effective Ukrainian drone operators are.
We learned that some of our units have not learned the basic lessons from Ukraine. But I try not to over learn. You know what I mean? Those are good things to learn and we should get those into our training track immediately. But it does not mean NATOʼs over or, you know, they canʼt defeat Russia. It just means they had a learning opportunity and they took advantage of it.
Video from NATO exercises, in which Ukrainian military defeated two battalions in one day.
412 бригада СБС Nemesis
However, perhaps it is time for Ukraine to teach others?
. I think NATO will constantly be coming to Ukraine to learn, and Ukraine will be offered the opportunity to train European countries. I think thatʼll be easier after a real ceasefire, not some fake Wyckoff ceasefire or the current condition of no ceasefire.
But it is worth mentioning here that the United States is the largest army in NATO.
Thereʼs challenges here, but also Iʼm very proud to work with the Ukrainian people and the Ukrainian Freedom Fund and Ukrainian armed forces, because I think this is where authoritarian empires come to die.
This attack was wrong. It was rife with war crimes. The attacks on religion in Ukraine, the attacks on the children on Ukraine, and the attacks on the critical infrastructure are all unacceptable.