Exclusive: Estonia’s Outgoing Military Spymaster on Russia’s War

It was the afternoon of February 24, 2022. Around 10 hours had passed since Russian President Vladimir Putin announced a “special military operation” against Ukraine, but the fighting was already inching dangerously close to Kyiv. Russian forces were trying to take control of Hostomel Airport at the north-western outskirts of Ukraine’s capital. Columns of tanks and other heavy equipment were pouring in from Belarus, one of Russia’s staging grounds, 80 miles away.

Roughly 500 miles to the north of Hostomel, at Kresty Airbase in Pskov, Russia, 18 Il-76 transport planes started their engines and headed towards the takeoff track. The planes were full of perhaps Russia’s most elite airborne troops from the 76th Guards Air Assault Division. The one thousand elite troops loaded onto the planes were highly trained, many of them seasoned fighters who’d fought in the First and Second Chechen Wars. Their objective was to fly to Kyiv and take control of the Ukrainian government.

The Il-76s were already halfway towards Hostomel Airport when Christo Grozev, The Insider investigative journalist and editor who has unmasked Russian assassins and saboteurs across Europe, first drew attention to them. “The only plausible goal would be to capture and subordinate Kyiv (and install a puppet government) today,” Grozev tweeted. “While the world is watching and doing almost nothing.”

In fact, one country’s intelligence service was watching and doing something.

Two sources confirmed to The Insider that Estonia’s military intelligence agency, officially known as the Military Intelligence Centre of Estonian Defence Forces, had sent an advance warning to their Ukrainian colleagues even before the 76th Guards boarded the airlifters.

Pausing before answering, Estonia’s military intelligence chief, Col. Margo Grosberg, said, “I cannot confirm or deny this,” when asked about it by The Insider. But Grosberg acknowledged that the Hostomel battle might well have been the most crucial event in the whole course of Russia’s full-scale invasion.

“If the ILs had landed at Hostomel, we might be today in a totally different situation than what he have,” he said.

Ukraine poured every resource it had around Kyiv to keep the planes from landing. It showered the airfield with artillery fire making the landing strip unusable. One of Russia’s Ka-52 “Alligator” attack helicopters was shot down and crashed on the runway making it virtually impossible for the Il-76s to land. After circling in the Ukrainian sky for some time, they flew back to Pskov.

On September 12, Grosberg turned 50. Lean and athletic, with close-cropped hair and an occasional grin so slight it could be drawn with a pencil, Grosberg was also celebrating his last day at the Estonian Defence Forces, a position he’s held for the last five years. The job was a fitting coda to three decades of service in Estonia’s military and now, Grosberg felt, it was time to have a “life outside of uniform.” Perhaps considering it his valedictory, he agreed to talk to The Insider. Although his public video updates about the situation on the ground have become routine and rendered him arguably the best known intelligence officer in the country, it is only Grosberg’s third ever sit-down interview.

Russia’s failure in building up their force presence before the war is one of the reasons the war has lasted more than one and a half years, Grosberg said. “The foundations of how Russia planned for the war were clearly wrong. It is the classic phenomena of dictatorships: the dictator is only served the information that people expect him to want to hear. He is not given the truth.” The problem persists still, according to Grosberg, as indicated by the firing of Gen. Ivan Popov, the chief of Russia’s 58th Army, who had given an unvarnished and unflattering appraisal of Russia’s defensive capability in southern Ukraine during the summer.

The Defense Forces Intelligence Center had started picking up alarming signals about Russia’s intentions in the Spring of 2021. Some of Russia’s military units were mysteriously relocating close to Ukraine’s borders. The movements struck Grosberg as small in number but still highly unusual. Then, in September 2021, Russia held its Zapad (“West”) military drill in Western Russia and Belarus. But after the large-scale exercise many units from the 41st Combined Arms Army of the Central Military District didn’t return home.

One of the Defense Forces Intelligence Center’s greatest successes was picking up early on Russia’s intention to annex Ukraine’s Crimean peninsula in 2014. “We saw it ahead long enough to make the alarm bells ring both in Estonia and NATO,” Grosberg told The Insider. But at the time, no one at the political level listened.

“When we take a look at the international reaction to the [annexation] of Crimea, it is clear that we weren’t listened to. Crimea led to Donbas,” Grosberg said, referring to the Russian-orchestrated launch of a “separatist” campaign to break parts of eastern Ukraine off from the rest of the country. “The result of Donbass is today’s Ukraine.”

Although Grosberg’s agency picked up early indications of the 2022 Russian invasion, too, this time they fell short of assessing the start of the war. “When you looked at the composition and concentration of Russia’s forces [along the Ukrainian borders], the answer was that they wouldn’t be able to do it. As it became clear, they really can make very stupid decisions and conduct the operation with only a third of the required forces,” he said.

However, Grosberg doesn’t belong to the school of thought that holds that Russia carries on making all the same mistakes and hasn’t learned anything in 19 months of a faltering campaign . “They are definitely not stupid. Or unable to learn.”

He believes it took Russia at least until the beginning of this year to cope with the errors that originated from the failed invasion plan. As proof of Russia’s adaptability, Grosberg asked when the last mention of a big Ukrainian HIMARS strike occurred, referring to the mobile artillery platform provided last year by the United States, which made an enormous difference on the battlefield, facilitating both the Kharkiv and Kherson counteroffensives. Grosberg answers his own question: It was New Year’s Eve, when Ukraine hit a large gathering of mobilized Russian troops at Mariinka, in the eastern Donetsk region.

“This indicates that Russia was able to learn and they adapted their logistics chains to stay out of reach of HIMARS,” Grosberg said. “The same goes for their decisions to pull out of northern Ukraine and Kherson. They understood that if they’d stayed, their situation could get really embarrassing.”

When the war began, Grosberg gave two commands to his subordinates. First, they should not count the dead and wounded because doing so would eat up too many resources. Second, they should not gather intelligence about Ukraine for fear that these could lead to leaks to the press.

He admits that these decisions have complicated his agency’s main task of understanding how Russian units are fighting, difficult enough to parse through the fog of war. Do they follow their tactical and doctrinal plans or are there discrepancies? If so, is it because of lack of personnel or for other reasons? All this knowledge is intended to help the Estonian Defence Forces be better prepared and equipped in the event of Estonia and NATO’s own war with Russia.

Grosberg has visited Kyiv only once during the war, shortly after Russia retreated from the capital region in April 2022. He explains he doesn’t want to be a bother to people who are actively in a war to defend their country.

Still, Grosberg maintains close connections with his Ukrainian counterpart, Lt. Gen. Kyrylo Budanov, the head of Ukraine’s increasingly high-profile military intelligence service, known by its acronym HUR.

Given Estonia’s history of occupation and illegal absorption by the Soviet Union and geographical location as a NATO ally on the Russian border, Grosberg’s job has almost singularly focused on the revanchist neighbor to the east. Similarly, The Poles, Finns, Latvians, Lithuanians and Ukrainians have for years paid very close attention to every aspect of the Russian military’s true capabilities, which were grossly overestimated by analysts in Western Europe and North America. Though he didn't say so during the course of the interview, Estonian military specialists were more prescient about what Russia could do versus what it wanted to do. Grosberg’s own biography speaks to his acute reading of the adversary.

As a teenager in the 1980s, he joined the Seamen’s School in Tallinn, Estonia’s capital, where all but two subjects were taught solely in Russian, and never by native Estonian instructors. Almost all of his classmates spoke Russian. Grosberg aimed to become a long-distance seaman because at the time it seemed the only feasible way to experience life outside the Soviet Union. He didn’t graduate because the Russian-language mathematics requirement proved an “insurmountable obstacle.”

On one of his visits to Kyiv before the war, Budanov gifted him an old Dnepr sidecar motorcycle (Grosberg is an avid collector of old motorbikes). But Estonia’s strict anti-corruption regime prevented Grosberg from accepting it. After the Russian assault on Kyiv, Grosberg asked Budanov for a more precious bauble: a Russian unmanned aerial vehicle, which Ukraine had downed in good condition. (The Insider was asked not to disclose the model UAV for reasons of operational security.) Budanov obliged and the Defense Forces Intelligence Center was able to study the weapon at its headquarters, giving Estonia technical insights into how best to defend against it. Grosberg has since returned the drone to Ukraine.

So where does the war stand as of now, in the midst of Ukraine’s sluggish but progressing counteroffensive to sever Russia’s land-bridge to Crimea in the south?

Grosberg estimates that Putin has enough resources to continue waging the war against Ukraine “at least as long as it has already been ongoing.” But this depends on several factors outside of Moscow’s and Kyiv’s control. “It depends on if the sanctions hold and how well we can implement them. It largely depends on how well we as the West can endure and how well we recognize that it is not just a piece of land. Ukraine is fighting over the same values that we respect and protect. As long as we understand this, the situation is satisfactory – far from good, but satisfactory.”

Another factor explaining why Russia hasn't been strategically defeated yet is the West’s initial reluctance to arm Ukraine before that abortive airbridge to Hostomel was even attempted. “Now, 550-plus days into the war, we have agreed to supply Ukraine with weapons and equipment that Zelensky asked for on Day 1,” Grosberg said. “If these had been granted right then and had we not delivered heavy equipment a few pieces at a time, the situation could be much different.”

F-16 fighter jets and ATACMS, Grosberg insists, will bring Ukraine “one more step closer to victory” but won’t be “silver bullets” that will decide the war. “Russia is not sitting idly and waiting for the F-16s to arrive. They are taking measures to adapt against them and they have nine months to do so.”

Grosberg isn’t much persuaded by the argument that providing these weapons systems will somehow cross Russia’s “red lines” for escalation, including the use of nuclear weapons.

“As the West didn’t have any red lines in the Syrian civil war,” he said, referring to President Barack Obama’s claim that the use of chemical weapons would precipitate a U.S. military intervention in that conflict, “Putin similarly doesn’t have any specific red lines in Ukraine. I don’t see the threat of tactical nuclear weapons as significantly high.”

How long will it take Russia to restore its military capabilities after the war? Russia still has roughly 6,000 tanks and between 8,000 and 9,000 armored vehicles in its inventory, Grosberg said. If it needs to “cannibalize” two vehicles in order to get one that actually works, it could still mobilize 2,000 tanks and 3,000 armored vehicles.

“Putin has declared that Russia’s aim is to modernize up to 500 tanks a year. According to this calculation they’d be ready to attack a neighbor again in four years.”

A lot depends on when and how the war will end.

“Let’s take a scenario where the war ends today. Sanctions will be upheld and Russia’s economy will continue to stagnate. [Russian Defence Minister Sergei] Shoigu’s plan is to increase Russia’s army to 1.5 million. When the economy is down and jobs are scarce, it will be easy to recruit for the army. The cycle of training a petty officer is four years. Senior officers will come from the troops with battle experience. It is down to mathematics.”

At the same time, Grosberg is wary of assessing the progress of Ukraine’s counteroffensive. Russian defenses can collapse in a day but as well may not before the onset of winter. “The hope or expectation for Ukraine to reach the Azov Sea… I wouldn’t dare to say it will happen before the winter.”

The balance of forces is largely equal and now the fight is not over territory but about which side can force their will on the other, Grosberg explained. It’s also about constantly keeping pressure that can eventually cause a breakthrough.

“The reason why the Russian lines broke a year ago in Kharkiv was that troops from one Russian unit witnessed how another unit was retreating. They didn’t know but the decision for the first unit to retreat was tactical and justified. It wasn’t panic. But it caused panic among the lines of the unit seeing it and that led onto the total collapse. It was all about holding constant pressure on Russian forces. Simple as that.”

If Ukraine doesn’t achieve a breakthrough before the winter, a lot will hinge on the weather. Should the season be mild and the ground remain unfrozen, the result will likely be an artillery battle as was the case last year. If it’s a harsh winter, we could see large maneuvers on both sides.

“It is very probable that Russia will take the time to dig in even more, to build new fortifications and prepare for the spring,” Grosberg said.

Grosberg leaves his post as Estonia’s military spymaster relatively pleased with what he and his service have accomplished. He recounts what Gen. Martin Herem told him when Herem assumed office of Commander of the Estonian Defence Forces, equivalent to the U.S. Chairman of the Joint Chiefs of Staff, in December 2018. Grosberg had been chief of the Defense Forces Intelligence Center for only a few months.

“Failure is written into your job description,” Herem said before painting a dire scenario. Imagine that Estonian military intelligence raises an alarm that the war with Russia is about to start. The Estonian Defense Forces would immediately pivot to a wartime formation, mobilize and conscript thousands of men from their everyday lives, draining the nation's economy. This posture would be maintained for several months. Now imagine the war never came.

“We’d never know why. Was it because the Russians never intended to attack us or was it because we were prepared and scared them off? But it’d be close to impossible for the commander of the Defense Forces to ask the government to repeat the process for a second time. That’d be a failure. On the other hand, if I didn’t raise the alarm and ask the government to announce mobilization, we’d also lose.”

That Grosberg was never confronted with such a Hobson’s choice was a lucky break. It’s also the reason his “house” was kept in order for the past half-decade, even as the largest and most devastating land war in Europe since World War II was launched fewer than a thousand miles away from Tallinn.

“The best accomplishment is that our adversary has not been able to develop ahead of us, such that they could surprise us. For all that, it really is a constant struggle.”

Cover photo: Kiur Kaasik / Delfi Estonia