The Longest and Worst Sieges in history
The Longest and Worst Sieges in history

The Longest and Worst Sieges in history

Larry Holzwarth - July 30, 2020

The Longest and Worst Sieges in history
The Siege of Vicksburg required coordinated operations between the Union Army and Navy. Wikimedia

12. Siege of Vicksburg. 1863

In May, 1863, Union forces under Ulysses S. Grant approached the Confederate stronghold at Vicksburg, an important rail and river junction which controlled access to the Mississippi. Despite outnumbering the Confederate defenders by about two to one, Grant’s probing of the formidable defenses led to his decision to capture the city by siege. The Confederate fortifications included rifle and cannon pits, redoubts, artillery placed so as to generate wide fields of fire, mortars and heavy guns, raised fortresses, and interconnecting trenches. The railroads leading into the city were well protected, allowing the Confederates to resupply both food and ammunition.

Grant probed the defenses in late May, accomplishing little other than casualties, before opening siege operations. Union troops dug trenches, moving them steadily closer to the Confederate positions during the month of June. Confederate troops underwent nightly heavy bombardment from Grant’s artillery and from naval gunships in the Mississippi River. The Navy alone fired well over twenty thousand shells into Vicksburg’s defenses and the city itself over the course of the siege. By the end of the month of June, about ten thousand of Vicksburg’s defenders – more than half – were unfit for duty due to sickness.

The Longest and Worst Sieges in history
Civilians attempted to escape the shelling by living underground. National Park Service

13. Civilians at Vicksburg lived under ground

To escape the ferocity of the combined Union bombardment, civilians within the Vicksburg perimeter abandoned their homes and moved underground. A long ridge ran along the Confederate lines, with the side facing the central portion of the city shielded from Union fire. Citizens dug caves in the side of the ridge, and some were furnished with items from their homes, including rugs, chairs, tables, and beds. As food supplies in the city dwindled, others remained in their homes, sheltered in cellars, in order to guard their vegetable gardens from starving Confederate troops. The Union troops concentrated their fire at Confederate defensive positions, though inevitably stray shells struck private homes and businesses.

The underground caves numbered over 500 during the month of June, and were easily seen by troops from many positions along the Union lines. Union soldiers called the ridge the Prairie Dog Village, its occupants by extension were called Prairie Dogs. Despite the ferocity of the bombardment few civilians fell to Union fire, though deaths from malnutrition and disease were high. Vicksburg fell to the Union on July 4, 1863. It was the same day Robert E. Lee’s Army of Northern Virginia began its retreat from Gettysburg, marking that Independence Day as the turning point of the American Civil War.

The Longest and Worst Sieges in history
The Siege of Sevastopol during the Crimean War previewed the destructive power of large, rifled cannon. Wikimedia

14. The Siege of Sevastopol, 1854-1855

The eleven month siege of Sevastopol represents one of the most revered moments in British military history, though it was hardly just a British operation against the Russian Empire. French, Sardinian, Egyptian, and Ottoman troops were involved as well, as were the French Navy. Eventually, German, Italian, Polish, and even Swiss troops joined in the attempt to capture the Black Sea port and end the Crimean War. The bulk of the troops defending Sevastopol were sailors of the Russian Navy, transferred from ships in the harbor which were scuttled to prevent Allied ships from penetrating the port. Command of the defenses was under three admirals of the Russian fleet, two of whom were killed in the siege.

On the Allied side, the French suffered the most casualties, with over 10,000 dead from combat, and over 50,000 from disease. In contrast, the British lost just under 5,000 to combat injuries, and about 16,000 to disease. Russian deaths exceeded 100,000. The fall of Sevastopol was the climactic event of the Crimean War, and in many ways foresaw events of the American Civil War. The siege saw the first use of railroads to move troops and supplies along the battlefront, and the first attempts to protect the sides of wooden ships with armor as they engaged in battle, through iron chains draped over the ships’ sides.

The Longest and Worst Sieges in history
The Siege of Ostend led to a Spanish victory which bankrupted the royal treasury. Wikimedia

15. Siege of Ostend, 1601-1604

The ability of sea power to affect military affairs on land was demonstrated dramatically by the over-three-year siege of Ostend, during a series of conflicts known collectively as the 80 Years’ War. The prolonged siege claimed the lives of over 100,000 soldiers, sailors, and civilians, and otherwise accomplished very little. The Dutch defending Ostend were resupplied, and reinforced, by sea, by their own ships and ships and troops from England. The Spanish attackers opened the siege in the summer of 1601 with a series of massive assaults, which were bloodily repulsed, after which the battle turned into one of attrition.

The British adopted the practice of assigning garrisons to the fortifications around Ostend for limited tours of duty before revolving them out. The practice helped minimize disease, often a weakening factor in besieged forces. By the time the Spanish finally took the city in September, 1604, there was a very little city left, it having been leveled by more than three years of continuous fighting. Technically the siege was a victory for the Spanish and a disheartening defeat for the Dutch, but its cost led to the Spanish court collapsing in bankruptcy three years later.

The Longest and Worst Sieges in history
French forces in Southeast Asia found the Vietnamese unwilling to capitulate in the mid-19th century, a lesson they failed to retain. Wikimedia

16. The Siege of Tourane, 1858-1860

In 1858, in response to the Vietnamese Emperor’s order to execute two Spanish Catholic missionaries the preceding year, French Emperor Napoleon III dispatched a joint Franco-Spanish expedition to chastise the Vietnamese ruler. In early September, the European forces seized Vietnamese fortifications on the Da Nang River, including the fortress of Tourane, which they promptly garrisoned. The bulk of the European forces then departed to attack Saigon. Once the French ships were gone from the Da Nang River, the Vietnamese promptly placed the garrisons under siege. There was relatively little fighting, and the Vietnamese adopted the strategy of denying supplies to the garrison, hoping to starve them into submission.

The French soon found themselves in a costly and frustrating quandary in Vietnam. They concentrated forces in one area only to find resistance arise in another. Pacifying the countryside proved to be an elusive goal. In early 1860, French commanders decided to concentrate their forces in the Saigon region, ignoring the smaller cities and hamlets. The garrisons at Tourane and around Da Nang were abandoned by the French, ending the almost two-year siege. The French lost 128 men in combat, and several hundred more to tropical diseases during the siege, before acknowledging the positions did little to further their overall situation in Vietnam.

The Longest and Worst Sieges in history
Turkilsh deserters photographed in Georgia during the Russo-Turkish War. Wikimedia

17. The Siege of Plevna, 1877

The Russo-Turkish War of 1877-78 was a result of the rising nationalism of the Balkan provinces and their desire for independence from the Ottoman Empire. They were supported by Russia, which desired recovery of territory lost through the Crimean War, and a re-establishment of their dominance of the Black Sea. The Russians established the ill-treatment of Christians in the Ottoman Empire as a casus belli, and a coalition force from Serbia, Montenegro, Bulgaria, Romania, and Russia attacked Turkish troops in the Balkans. With Constantinople threatened, Turkish forces held a fortified position at Plevna, forcing a siege of 145 days.

There was never much doubt as to the eventual outcome of the siege, with Russia and its allies fielding about 130,000 troops against fewer than 70,000 Turks and their allies. The siege was conducted, by the Turks, as a delaying action as its diplomats urged the western European powers to intervene. About 25,000 casualties were suffered by the Turks before they surrendered their positions in December, 1877. They inflicted about 50,000 casualties on the Russians. Though the siege resulted in Turkish surrender and a technical Russian victory, it was successful in buying the time for intervention by the west, primarily from the British Empire and its powerful fleet.

The Longest and Worst Sieges in history
Japanese 11 inch siege battery shelling Port Arthur. Wikimedia

18. The Siege of Port Arthur, 1904-1905

The largest land battle of the Russo-Japanese War, the siege of Port Arthur provided a glimpse of the fighting to be expected during the First World War one decade later. Machine gun nests, entrenchments topped with barbed wire, searchlights, control of troop movements by radio transmissions, electrically charged fences, rapid-firing light cannons, and bolt action magazine fed rifles all made their appearance. The Japanese believed they could capture the heavily fortified Russian positions at Port Arthur through a quick and decisive assault, instead, it took five months and a day. Port Arthur was heavily defended as a base for the Russian Pacific Fleet.

During the course of the siege, the fleet was destroyed by Japanese bombardment, though some ships were scuttled to prevent them from falling into Japanese hands. The Japanese suffered over 91,000 casualties during the siege, compared to about 31,000 for the Russians, though another 24,000 surrendered. The Russian defeat was a blow to the Tsar and created further unrest throughout much of the Russian Empire. The following year mutinies among military units, worker strikes, and other forms of protest led to constitutional reforms and a weakening of the Tsar’s grip over the Russian people.

The Longest and Worst Sieges in history
T. E. Lawrence gained fame as Lawrence of Arabia during the fight for Medina. Wikimedia

19. The Siege of Medina, 1916-1919

The Islamic Holy City of Medina was in the Ottoman Empire during the First World War, when it underwent the longest siege of that conflict. During the siege and other operations in the Arabian desert, Thomas Edward Lawrence gained enduring fame as Lawrence of Arabia. Sharif Hussein of Mecca sided with Lawrence and the British against the Caliph, besieging Arabian forces aligned with the empire in Medina. The forces which remained loyal to the empire and defended Medina were led by Fahreddin Pasha. The Arab revolt against Turkish rule was divided along tribal and religious lines, but with the Turks fighting alongside the Central Powers, it was in the interests of the British to encourage rebellion among the Arabs.

The Ottoman Empire withdrew from the war at the end of October, 1918. By then, the forces defending Medina had repulsed hundreds of attacks on the city and the railroad which connected it to supplies. Casualties on both sides were heavy throughout the siege, and bloodthirsty reprisals on prisoners and non-combatants were common. Following its exit from the war, the Ottoman Empire directed the remaining defenders of Medina to surrender. Pasha refused, and the city continued to hold out for more than two months. The garrison finally surrendered in January, 1919, after which Arab troops raided and pillaged the Turkish homes for two weeks. The total casualties during the long siege remain unknown, though Lawrence wrote of the heavy losses to both sides, including of women and children.

The Longest and Worst Sieges in history
Republicans dressed in the vestments of priests they murdered attest to the ferocity and atrocities of the Spanish Civil War. Wikimedia

20. The Siege of Madrid, 1936-1939

The siege of Madrid took place during the Spanish Civil War, between the factions supporting the Republic, and referred to collectively as Republicans, and the fascist Nationalists under Francisco Franco. After the Nationalists failed to capture the city in fierce battles in 1936, it came under a protracted siege. Italian and German bombers struck targets within the city’s defense lines throughout the siege, with air cover provided by fighter aircraft. It provided the first appearance in the battle of the new and modernized German Luftwaffe, alarming both the French and British air commands. The Italian efforts were somewhat less disconcerting.

Bitter divisions among the Republicans led to infighting among the leaders of the various factions, as the city continued to undergo bombing throughout 1937 and 1938. Franco’s Nationalists gradually tightened the noose around Madrid, adding artillery shells to the bombs, and the city’s civilian population suffered from starvation, disease, and the secret police executed suspected Nationalist sympathizers. Madrid’s defenses collapsed in March, 1939. Over the ensuing four years, Franco’s regime executed or imprisoned those who had opposed him, with over 200,000 dying in prison or executed outright. They can be added to the number of casualties of the siege, which have never been agreed upon by historians but were in the hundreds of thousands.

The Longest and Worst Sieges in history
Soviet anti-aircraft guns near St. Isaac’s Cathedral during the defense of Leningrad. Wikimedia

21. The siege of Leningrad, 1941-1944

The siege of Leningrad is often commemorated as the 900 days. It involved Finnish, German, and Soviet armies, the navies of Great Britain, Poland, the United States, Germany and the Soviets, and hundreds of thousands of civilians. It accounted for over 2 million military casualties among the armies, and an unknown, but brutally high number of civilian casualties. Soviet secret police (NKVD) records left reports of cannibalism, including the murder of individuals to use them as food. A division of Spanish troops, known as the Blue Division, served with the German Army during the siege, though officially Spain remained neutral throughout the war. The Soviets lost over 44,000 men against the Blue Division.

Leningrad was the target of the German Army Group North when Operation Barbarossa launched on June 22, 1941. Finnish troops entered the war to recover territory lost to the Soviets during the Winter War, and helped isolate Leningrad from the north, while the Germans advanced rapidly to the north and east. By early September, 1941, the Germans controlled all the roads entering Leningrad, effectively besieging it that month. Hitler made the reduction of Leningrad his first priority for the massive operations on the Eastern Front, and the Soviets fought with ferocity to prevent the city from falling into German hands.

The Longest and Worst Sieges in history
Leningrad endured over two years of near constant bombing and shelling. Russian International News Agency (RIAN)

22. Leningrad’s civilian population suffered throughout the long siege

On September 21 in Berlin, the OKW (the German High Command), made the fateful decision not to occupy Leningrad, but to destroy its population through starvation and bombardment. The decision was based on logistics. Occupation of a populated city by the Germans would place the responsibility of feeding the civilians on the Wehrmacht. The decision was made to starve the Soviets, allowing the Finns to enter the city if they chose to, and after the city capitulated the survivors were to be escorted into captivity deeper in Russia. Plans were made to demolish the city with explosives, bulldoze the rubble, and abandon the areas north of the Neva River to the Finns. On October 7, Hitler endorsed the plan.

Finnish plans did not include advancing on Leningrad, despite pleas from the Germans to do so throughout the siege. Nor did they bomb the city and its defenses, though German leaders implored them to do so. Finnish plans included the recovery of territory previously lost, with some advanced positions to consolidate defenses. The Finnish lines did isolate Leningrad, impeding Soviet attempts to supply the city and reinforce the troops defending the fortified region surrounding Leningrad. Beginning before the siege and continuing to March, 1943, Soviet troops fought to maintain a corridor through which to evacuate civilians from the city and its suburbs. Less than half of the prewar population of Leningrad were evacuated.

The Longest and Worst Sieges in history
Soviet anti-aircraft guns in Leningrad. Ammunition for defense took precedence over food for civilians. RIAN Archive

23. German aerial bombardment targeted civilian facilities

As it had during the siege of Madrid, the Luftwaffe targeted non-military areas in the city and its outlying suburbs. In September, 1941, the largest single air raid of the entire siege bombed hospitals, markets, bazaars, and the city’s open streets. Five hospitals alone were hit by German bombs. On some days, the Germans arrived in waves, with the bombing continuing throughout the long day. As had the Americans at Vicksburg, many Soviets turned to living underground. Throughout the siege, Russian Air Defense was in the hands of the navy fliers of the Baltic Fleet. Over 100,000 sorties by the navy fliers opposed the German air attacks, with heavy casualties on both sides.

In August, 1941, the Germans consolidated their positions around Leningrad’s defenses and heavy artillery added to the pounding of the city. The following year heavier guns arrived to continue the destruction. In both 1942 and 1943, the intensity of the bombardment and the weight of shells fired into the city increased from the preceding year. The German Army captured and looted several of the Imperial Palaces outside of the city, including the Peterhof and Catherine Palaces, with organized logistics trains carrying their art collections and other valuables Germany. Meanwhile, the Soviets organized a logistics system of their own, which became known as the Road of Life.

The Longest and Worst Sieges in history
German ammunition supply column before Leningrad. BildesArchiv

24. The Road of Life sustained the Russian defenses

A small strip of land remained within Soviet hands, connected to the southern part of Lake Ladoga, north of Leningrad. Hitler’s generals pleaded with the Finns to occupy it, though the Finns demurred over moving any closer to the city. It was the strip of land and the lake itself which provided Leningrad with a means of obtaining supplies, and evacuating the wounded and civilians. During the winter, trucks drove across the strip and across the frozen lake. During the summer, Russian boats crossed the lake, carrying the food and other supplies which kept the city alive. They returned bearing refugee civilians to safety. The lake was kept secure by a naval flotilla, the land section by Soviet troops. They were not secure from air attacks.

In December, 1941, after Soviet counterattacks strengthened their defensive positions, a short railroad was constructed along the Road of Life, allowing faster delivery of larger amounts of supplies to the city. In 1942 an oil pipeline was built along the corridor, which was called the Artery of Life and which provided badly needed oil. By 1943 Soviet attacks had pushed back the Germans to the point the supply route could be expanded and enlarged, and the area was more heavily defended with anti-aircraft guns. The Road of Life nonetheless operated for the most part during the winter months, with warm weather supplies being far outstripped by the winter operations.

The Longest and Worst Sieges in history
Soviet barges carrying supplies to besieged Leningrad across Lake Ladoga. RIAN Archive

25. The siege of Leningrad caused horrendous civilian casualties

According to some historians, the loss of civilian life in the siege of Leningrad equated to genocide. 1.5 million Soviet civilians and soldiers died during the siege, with most of the civilian deaths attributed to starvation. Over 1 million additional civilians died of starvation while being evacuated from the city. The siege was the worst in history in terms of the numbers killed. Well over 500,000 Germans were killed in the siege before the Germans withdrew in the face of Russian counterattacks beginning in January, 1944. NKVD records, finally released in 2004, indicated cannibalism was wider spread in the city of horrors than previously believed. In April 1942 alone, the NKVD arrested more than 300 civilians for cannibalism. The majority were women.

Most of the city was destroyed by the German aerial and artillery bombardment, its infrastructure left in ruins and its people decimated. The United States Military Academy at West Point published a study which estimated more Soviet casualties that occurred during the siege than those suffered by the combined British and American armies for the entire war, including those in the Pacific Theater of Operations. There have been sieges of longer duration before and since Leningrad, including that of Kosovo, but none approach it in terms of human cost. The city has since been entirely rebuilt, with some historic sites restored. It is today known once again as St. Petersburg, as it had been under the Tsars.


Where do we find this stuff? Here are our sources:

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“Aztec capital falls to Cortes”. This Day In History, August 13.

“Vicksburg”. Article, American Battlefield Trust. Online

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“The Last Emperors of Vietnam: From Tu Duc to Bao Dai”. Oscar Chapuis. 2000

“Great Sieges of History”. William Seymour. 1991

“The True Story of Lawrence of Arabia”. Scott Anderson, Smithsonian Magazine. July 2014

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