This is a story about corruption — a destructive force that held back a campaign that Muscovite Tsar Ivan Vasilyevich, the Terrible, planned in 1567 against the Grand Duchy of Lithuania over the Livonian heritage.

Almost 500 years later, the same force slapped a Russian leader in the face — a leader who, feeling overconfident, launched his Ukraine campaign over the Soviet legacy.

The Principality of Muscovy in the 16th century was not yet Russia. That would come later: Peter the Great thought it would be a good idea to rename his newly forged empire in order to claim the lands of Kyivan Rus. But Muscovy in Ivan’s time already flexed its muscles and showed its teeth to its neighbors.

Ivan Vasilyevich’s objective was to advance westward and capture Slavic towns and fortresses, opening a path to the Baltic Sea. His first target was the fortress of Velikiye Luki — a strategic gateway to the Lithuanian heartland. Success required siege artillery: heavy cannons, the kind that had shattered the walls of Kazan and Polotsk.

16th century portrait of Ivan by Hans Weigel. Wikipedia

Unlike Western Europe, which had made some advances in building stone roads, the tsar didn’t bother with constructing transportation veins. Since the lands were still in boyar (noble) hands, they were responsible for infrastructure and maintenance.

In the event of the tsar’s needs, the boyars were obliged to facilitate the passage of troops, weapons, and supplies through their domains. If necessary, their men had to mobilize serfs — literally cheap labor — for the sovereign’s traction, shipping, or whatever project the tsar had in mind. On their own expense, of course.

Like any ruler, in important matters Ivan Vasilievich relied on a cohort of literate and smart men who acted swiftly and decisively in the tsar’s name. Let me introduce you to Russia’s first public service officials — dyakons, or dyaks [djak]. These could be boyar sons, military, junior clergy and even merchant class men.

During wartime — and those times never ended in the 16th century — military logistics was part of their job. In the absence of roads as we understand them, moving all the artillery from Moscow, Tver, and Novgorod to the staging grounds near the western border was a hell of a task. Each barrel weighed around one ton. The journey covered more than 400 kilometers and lay through the domains of Ivan’s aristocratic subjects.

The man in charge

Historical sources are contradictory about who exactly was in charge of transporting heavy cannons to the battlefield. Most documents, however, point to a dyakon named Ivan Mikhailovich Viskovaty, a real historical figure executed in 1570 or 1571 for alleged treason. Viskovaty was literate, meticulous, and ambitious. He had served in the Posolsky Prikaz (Muscovy’s foreign office) and had handled logistics for earlier campaigns.

Getty Images

Viskovaty’s task was not just hard but nearly impossible: move 50 heavy cannons, each requiring thirty oxen or two hundred men to haul, through terrain that turned to calf-deep mud after a single rain. His only authority was the Tsar’s seal — and the threat of disgrace. As if that were not enough, he also had to persuade every boyar along the route to provide labor for traction. No reimbursement was offered.

The planned route passed directly through the ancestral lands of several powerful boyar families: the Sheremetevs, the Obolenskys, and the Vorotynskys. These lands were dotted with villages whose peasants owed labor obligations to their lords. If the artillery train passed through, the boyars would be required to provide hundreds of peasants for corvée labor — clearing roads, hauling ropes, dragging cannons out of mud.

This would devastate the harvest. It would also expose the boyars’ estates to the chaos of a passing army: theft, destruction, and the ever-present risk of being blamed for any mishap.

Under these circumstances, speaking about when exactly the barrels were due to arrive was a pure joke. “The sooner the better” or “when God willing desires” was a normal estimate — the 16th-century equivalent of saying “probably this or next month” today.

The tsar realized the hardship his entrusted dyakon was facing and left him to handle the situation alone, marching ahead with his streltsy — infantry troops armed with arquebuses, axes and sabers.

Bargaining the passage

Dyakon Viskovaty, too, was aware of his time constraints. Choosing the itinerary was at his sole discretion. So why not combine the long journey with financial gain? Making money with a state seal was easy: its holder could command the best accommodation, the best meals, the strongest laborers, and the most beautiful women. And, naturally, gifts and cash to improve his mood.

The boyars whose lands lay along the original route of Viskovaty’s artillery train soon learned of their predicament. They were not fools. They understood that a dyakon with the power to choose the itinerary and means had more power than themselves. He could literally take everything from them.

(It was the default system setting in the early medieval Muscovy, borrowed from the Mongols, successfully adopted, and thriving in today’s Russia.)

According to Muscovite chronicles — which are likely biased in favor of the powerful — the dyakon in charge of artillery transportation demanded money from landlords to avoid their territories.

Forensic facial reconstruction of Ivan IV by Mikhail Gerasimov, 1963. Wikipedia

Some sources say it was Viskovaty’s initiative to levy bribes from landowners; others claim the aristocrats had volunteered to compensate the zealous public servant. Whether the dyakon ventured into blackmail or accepted kickbacks remains unclear. However, it is documented that he chose to circumvent lands of owners who refused to cooperate regarding the money-for-going-stray scheme.

Each time a deal was struck, the itinerary changed. Delays prolonged. Resources wasted. Victory postponed.

The tsar’s fury

There isn’t a single documented date from the chronicles specifying exactly how many days or weeks the cannons were stuck in the mud. However, based on the logistics of the Livonian War and the distances involved, the delay was likely in the range of four to six weeks.

Heavy bronze guns often required hundreds of men or dozens of oxen to move a few kilometers a day. Usually, this took weeks in good weather. When wheels sank to the axles at specifically difficult fords — where the water was deep, the bottom was muddy, and the surrounding terrain was unwalkable — crews often had to build corduroy roads (logs laid crosswise) or wait for the ground to freeze, which adds 1–2 weeks for a single crossing.

Now add the frequent itinerary changes that complicate the calculus.

The campaign was planned for late summer or early autumn. Since the journey was over 400 kilometers on dirt tracks, a delay of a few weeks was enough to turn dry roads into “bottomless” swamps, effectively ending the campaign season.

Ivan the Terrible was at the staging ground, waiting. When he saw the artillery arrive — more than a month late, with two cannons abandoned in the mud and a third cracked from improper handling — his face turned the color of curdled milk.

And the tsar’s mood shifted from frustration to storm and lighting. The nickname “Terrible” came not because he was simply bad, he was literally a terrible person.

“Treason”! That word was always his first and final explanation for any failure. Usually, the execution followed minutes or hours after the accusation, with little or no investigation. This time was different.

Ivan ordered an investigation. The man he chose to lead the inquiry was another dyakon: Vasily Shchelkalov (also a real figure) — a ruthless, efficient, and deeply loyal servant of the tsar. He had a clerk’s love for documents and a torturer’s gift for extracting confessions.

Shchelkalov began with the obvious question: who had ordered the route change? The answer led to Viskovaty. Under questioning — and the threat of the knout — Viskovaty broke. He named the boyars who had paid him. He produced a ledger, carefully annotated, listing every bribe.

The investigator presented his findings to the Tsar. But he did not stop there. As he interrogated the boyars, a more alarming pattern emerged. The bribes had not been merely about sparing lands. Several of the boyars — the Vorotynskys in particular — confessed to a desire to see their monarch fail and being replaced with “someone more fit.”

The air was getting filled with the smell of human barbeque. The line about greed and negligence got pushed aside and the line about treason gained momentum. The tsar demanded a name. He heard it: Prince Vladimir Staritsky, the tsar’s first cousin, was a quiet candidate profiled by opposition nobility as “the natural heir” and “a better man for the throne.”

One of the Sheremetev retainers, under torture, even revealed a plan: if the campaign failed, the tsar would be weakened. The boyars would demand Staritsky be made co-ruler — or perhaps the sole ruler.

The artillery delay was not merely corruption, if seen from this new angle. It could have been cleverly orchestrated sabotage on behalf of a pretender. Whether dyakov Viskovaty was a participant in the plot or simply acted as a useful idiot, we’ll never know.

For the paranoid Ivan the Terrible, however, this was the nightmare he had feared since the dynastic crisis of 1553. He ordered Staritsky arrested and brought to Alexandrovskaya Sloboda, the oprichnina headquarters. There, Ivan accused him personally of plotting to overthrow him.

The conviction of the Staritsky family. Generated with AI.

Staritsky defended his innocence and denied knowledge about the corrupt dyakon’s zig-zagging with guns — which his ruling cousin did not believe, though he had no direct evidence of the former’s guilt. Suspicion was reinforced by Staritsky’s mother, Princess Efrosinya, who had been heard — years earlier — boasting that her son would rule.

For Ivan, that was enough to convict the supposed rival.

In October 1569, Ivan the Terrible forced Vladimir Staritsky, his wife, and his young daughter to drink poison. Princess Efrosinya was called to the palace for explanations but was murdered by guards on the road to Moscow. The boyars named in the bribery scheme were executed or exiled.

What about dyakon Ivan Viskovaty? He was publicly disgraced and beheaded in 1570 or 1571.

The tsar never acknowledged that his dyakon’s greed was the starting point of a long thread that led to the discovery of a possible plot against him — saving literally his crown and life, even by accident. Nor did he sanction bribery or incompetence. Since he was the biggest recipient of bribes in all forms across his vast principality — for which he was “entitled” as the supreme leader — he only punished disloyalty.

The lessons learned

The campaign against Lithuania failed that year. The fortress of Velikiye Luki would not fall until the following decade, under different commanders and at terrible cost.

The tsar learned one lesson: no one could be trusted.

The dyakons learned in turn another: the Tsar’s favor was a sword that cut both ways.

And the boyars learned the oldest lesson of all: the price of cutting a bargain behind the tsar’s back is sometimes paid not in rubles, but in blood.

The interrogation of Viskovaty. Generated with AI.

The modern Russian state has, to a large extent, inherited the features that Ivan the Terrible had embedded into his rule. Vladimir Putin — another paranoid ruler — has also surrounded himself with loyalists rather than competent professionals. He, too, has killed his political competitors and crushed the opposition.

The regime in Moscow relies today — as it did almost 500 years ago — on repression, bullying, and conquest. And Putin is one of the most corrupt statesman in modern history beyond any doubt.

And it’s hard not to notice how the Russian army — which Putin never stopped bragging about — got stuck in Ukraine precisely because of the same reason the mad Muscovite monarch failed in Lithuania.

Tanks abandoned for lack of fuel. Significant manpower annihilated due to poor training. No reliable equipment. Not enough weapons or ammunition. The entire world has seen the corrupt logistics and the true might of Putinist Russia.

Where had all that stuff vanished? The answer is simple: Stolen. This is what a kleptocratic regime does for a living.

Mr. Putin may feel like an academician when he lectures about history — one of his favorite occupations — but he is actually a poor learner.

***

p.s. A clarification is necessary. While this is a true story from the reign of Ivan the Terrible, there may be factual inaccuracies and I sincerely apologize for them. It is difficult to find reliable sources about Russia, because this country has been rewriting history books for years and because it is a major source of disinformation in the world today.

You are invited to contribute factual improvements and suggest reliable sources. I have done my best with the available materials. If better sources exist, I welcome them. Be constructive and polite.

I sensed parallels between the Lithuanian campaign of 1567 and the Ukrainian campaign of 2022, which initially failed for the same reason: corruption. This was my ultimate goal.

***

References and sources:

Pavlov, Andrei & Perrie, Maureen Ivan the Terrible https://www.taylorfrancis.com/chapters/mono/10.4324/9781315844374-9/culmination-terror-andrei-pavlov-maureen-perrie

Kleimola, Ann “Mistakes were made”: text and image in the Litsevoi Letopisnyi Svod account of the Staritskii rebellion https://journals.openedition.org/res/944?lang=en

Volkau, Mikola Zamki i drogi na białoruskim Podźwiniu w czasie wojny inflanckiej (1558–1583) / Castles and Transportation Networks in Podvine, Belarus, during the Livonian War (1558–1583) https://bibliotekanauki.pl/articles/32388132.pdf

Gawron, Przemysław Udział hetmanów litewskich w przygotowaniu kampanii wojennej na przykładzie zmagań ze Szwecją w roku 1625 https://bibliotekanauki.pl/articles/690163.pdf

Wikipedia contributors Vasily and Andrey Shchelkalov https://en.wikipedia.org/wiki/Vasily_and_Andrey_Shchelkalov

Wikipedia contributors (archived version) Vasily and Andrey Shchelkalov (2008 archive) https://wayback.archive-it.org/all/20080627051122/http://en.wikipedia.org/wiki/Vasily_and_Andrey_Shchelkalov

Wikipedia (Russian) Щелкалов, Андрей Яковлевич (Andrey Yakovlevich Shchelkalov) https://ru.wikipedia.org/wiki/%D0%A9%D0%B5%D0%BB%D0%BA%D0%B0%D0%BB%D0%BE%D0%B2%2C_%D0%90%D0%BD%D0%B4%D1%80%D0%B5%D0%B9_%D0%AF%D0%BA%D0%BE%D0%B2%D0%BB%D0%B5%D0%B2%D0%B8%D1%87

Wikipedia contributors Livonian War https://en.wikipedia.org/wiki/Livonian_War

The Free Dictionary (via The Great Soviet Encyclopedia, 1979) Shchelkalov, Andrei and Vasilii Iakovlevich (corrected working link) https://encyclopedia2.thefreedictionary.com/Shchelkalov%2c+Andrei+and+Vasilii+Iakovlevich

Belokurov, Sergey Alekseevich О посольском приказе (On the Posolsky Prikaz) — Chapter on the Shchelkalov brothers https://azbyka.ru/otechnik/Sergej_Belokurov/o-posolskom-prikaze/10

Taylor & Francis Group The Posolski Prikaz (from Russian Embassies to the Georgian Kings) https://www.taylorfrancis.com/chapters/mono/10.4324/9781315607313-88/posolski-prikaz-allen

The Free Dictionary Minister of Foreign Affairs (Russia) — includes Ivan Viskovatyi and Andrey Shchelkalov https://wwwencyclopedia.thefreedictionary.com/Minister+of+Foreign+Affairs+(Russia)