Outnumbered, cut off from any hope of rescue or support, operating secretly. The dramatic potential of troops or pilots conducting a raid has been well explored by film, television, and literature. The scenario even offers all the, for want of a better word, “fun” of being in the military without many of the responsibilities, such as looking out for the well-being of civilians or many other parts of protocol. It also offers the persons involved the potential for much more glory than most regular operations since the numbers are small enough that there’s less credit to spread around and less commotion for an individual’s contribution to be lost. 

Most raids are good primarily for wasting the enemy’s resources or extracting a specific target. Some, however, have changed the very shape of history and the courses of wars. While some are still kept under a shroud of secrecy that may never be lifted, some are so devastating in their impacts that they can’t be kept under wraps by either side. 

10. Operation Flipper

No one could say that the mission that Colonel Robert Laycock and his 59 other commandos were sent to on November 10, 1941, was unambitious. They boarded the submarines H.M.S. Torbay and Talisman intent on sneaking into Axis-controlled Tunisia, raiding Sidi Rafa. There they would kill Lt. General Erwin Rommel himself while also destroying the Italian high command in North Africa, effectively liberating the continent for the Allies. 

They didn’t even make landfall before things began to go wrong. A storm struck on November 14 and forced the Talisman aground, with only seven commandos arriving for the landfall. Despite around 50% of the personnel being knocked out without a shot being fired, Laycock decided to go ahead with the plan to assassinate Rommel and attack the Italian HQ. The weather continued to be a problem as they were bombarded with rain, but by November 17, they launched their two-pronged attack. 

While the commandos killed three German colonels and destroyed a supply dump, it turned out Rommel hadn’t even arrived, as the same weather that had given the commandos so much trouble had convinced him to stay in Rome. It turned out to be a steep price to pay as only two of the commandos returned to British lines at all, and that took them five weeks of subterfuge. A very loose and flattering film adaptation of the events called Raid on Rommel was released in 1971.  

Hopefully, this entry has gone to show that just because a raid was daring does not at all mean it was successful.

9. Raid on Boulogne 

As Napoleon Bonaparte said, if the French could be masters of the English Channel for six hours during the 1800s, they would be masters of the world. This was no idle boast to the British military, who watched the French draw together a navy with alarm. By 1804 the time had come to act, and the target was the 150 French ships in the fortified port of Boulogne. The British navy sent a flotilla of ships heavily laden with torpedoes, a brand new weapon designed by Robert Fulton. The raid actually inflicted light French casualties (about 14) and little damage on the French fleet. 

And yet it had an effect far out of proportion to material damage in one area: Morale. Spooked by the torpedo explosions, the morale of the French military sank, and the initiative to launch an invasion of the United Kingdom was replaced by panic. Ports were refortified instead of being prepared for an attack. Great Britain might have been saved by the Raid on Boulogne. Not bad for a raid that hadn’t cost the British a single casualty. 

8. The Great Raid of 1840

On March 19, 1840, leaders of Comanche and Penateka tribes in Central Texas were engaged in peace talks with Texas leaders. Owing to one freed hostage’s account, the Texan authorities threatened that unless all hostages were returned, every Native American participant could consider themselves a hostage. When the Comanche refused, a fight broke out which left more than 30 Comanche, including women and children, dead. So it was that by August 6, 1840, between 600 and 1,000 Comanche men under the command of Buffalo Hump rode into Texan territory in reprisal. 

First, they sacked the community of Victoria, killing fifteen as the rest huddled in the Southern district. The war party rode along the Guadalupe River, coming to a stop in and sacking the community of Linnville, outside San Antonio. The Comanches then retreated on August 8, but they made the mistake of carrying an oversized haul of loot and stolen horses with them, which slowed the party down enough for the Texans to organize a war party of their own. They caught up to the Comanches at Plum Creek and were estimated to have killed eighty of them in a surprise attack. As a result the Comanches never attempted anything like such a large and elaborate raid again, reverting to tried and true small-scale guerilla tactics.  

7. Morgan’s Raid

us is not an unabashed fan of Confederate raiders, considering what those under commanders like William Anderson did at Centralia.  Still, there’s no denying the daring and significance of many of their raids, especially in regards to lengthening the Civil War. Surely the one that John Hunt Morgan began on June 11, 1863, at the head of 2,400 cavalrymen was one of the boldest. He had been ordered to move from Sparta, Tennessee, and invade Kentucky to distract the Union armies, but he was not to cross the Ohio River under any circumstances. So on July 8, Morgan crossed the Ohio River with around 1,800 cavalrymen as the rest continued operations in Kentucky. While he was far from the largest Union armies, there were 100,000 Union troops against him, albeit widely scattered. 

It turned out Morgan’s orders had been much more reasonable than he would have liked, for the Union command quickly figured out where he was going. At Fayetteville, West Virginia the 23rd Ohio and 13th West Virginia Volunteers led by future president Rutherford B. Hayes ambushed Morgan on July 19th and cut his numbers in half. The Federals chased them to Salineville, Ohio, and captured Morgan and the remnants of his command on July 26. As we’ll see in a bit, that was nowhere near the worst thing to happen to the Confederate military that season.    

6. Belov’s Raids

TopTenz has written before about how the winter of 1941-1942 actually didn’t stop the Third Reich’s capture of Moscow and was quite bad for the Red Army’s counterattack. Still, one force of the Red Army came away from the largely disastrous counterattack with a massive credit under their belt. It was the 1st Cavalry Corps under General Pavel Belov. A large number of German divisions were positioned in a salient point in the Rhzev area, and Belov’s cavalry was sent behind the front in an attempt to cut the salient supply lines. 

The corps would find itself cut off, surrounded, and badly outnumbered. Yet Belov’s forces were sufficiently resourceful that they tied down seven divisions for six months, aided in no small part by the many partisans that were rallying against the Axis army as their extermination operations were making it clear they were not the heroic liberators many initially took them to be. Ultimately, Belov and roughly 2,000 under his command would break back out of the encirclement, and Belov would go on to become one of the most acclaimed Soviet commanders of the war.   

5. The Whitehaven Raid

For most of the American Revolution, it was taken for granted that all the fighting would take place in American territory as the crown had such an overwhelmingly superior army and navy. In 1778, John Paul Jones, who a year later would very famously capture the British ship Serapis after yelling “I have not yet begun to fight,” made to bring the fight to the home country by raiding the port town of Whitehaven in northwest England with its 400 merchant ships. Having sailed the Atlantic, Jones set out with thirty commandos in two boats to conquer the two forts and burn the merchant fleet to the waterline. 

For Jones’s boat, things went relatively smoothly. They landed, took their objective fort, and ruined the guns so that they could safely escape. The other boat, however, had problems that sounded like something out of Black Adder. First, the tide gave them so much trouble that they fell three hours behind schedule. Then when they belatedly made landfall, they went to the local pub and got drunk off liquor. When Jones caught up with them and understandably raged at the neglect of duty, he attempted to set fire to the town and ships, but the town’s fire brigade, bolstered as was English tradition since the 1666 London Fire, dutifully put the fires out promptly. Jones and company got away having neither suffered nor inflicted much damage, yet their exploit sent a wave of terror through the Isles that led to many sea towns being put on the alert for years afterward.    

4. The Doolittle Raid 

Anyone who’s seen Michael Bay’s 2002 film Pearl Harbor knows the Doolittle Raid was how the US Armed Forces saved face after the humiliation of four battleships being sunk and about 2,000 lives being lost during the sneak attack. On April 18, 1942, 16 B-25 Mitchells took off for Tokyo, starting more than half again over the original distance they originally intended. There would be no returning: They had to fly for China and hope they could land in airfields controlled by the Allies. 

The bombing killed 50 Japanese people, mostly civilians, and wounded about 400 others, but did little structural damage. So when the bombers were found to be too low on fuel to reach their airfield objectives and had to crash land, Commander James Doolittle’s belief that he would be court-martialed for losing 16 planes and three personnel while inflicting little damage on the enemy seems understandable. Considering the boost the attack had for US morale and the way it disrupted Japanese public sentiment to a point where it changed military strategy, it’s also understandable that he received the Medal of Honor instead. 

Initially ignored but increasingly more mentioned, the raid cost China’s population by far the most of any nation involved. Both because it revealed just how vulnerable Japan could be to air attacks from China and simply thirsty for revenge, the Japanese military launched a series of reprisals that by some accounts left hundreds of thousands of Chinese dead. If Doolittle’s men had given any sort of American gift to a Chinese person in compensation for kindness, they were very likely unknowingly giving that person a death sentence. It also seemed to influence the decision for just where to place the infamous Unit 731, as it was quite close to Chuchow, the Doolittle raiders’ intended destination. Such are the greatest sacrifices in war often overlooked.  

3. The Osel Air Raid

When the Third Reich launched Operation Barbarossa on June 22, 1941, and invaded the Soviet Union, they caught the Red military completely off guard, destroying 1,200 Soviet plans in a single day. By July they were launching bombing runs on Moscow itself. General Secretary Joseph Stalin caught wind of the effect the raids on Moscow were having on Soviet morale and so ordered air raids on Berlin itself in retaliation. 

This was no idle command, as Berlin was the best-defended city in Europe and tore through squads of Allied aircraft on the regular. So when 15 Ilushyin DB-3 bombers took off from Osel, Estonia for Berlin on July 7, 1941, the years’ obsolete planes were generally regarded as being sent on a suicide mission. Such was their condition that the crews needed to perform wing repairs on them in midair. 

Fortunately for them, Berlin’s anti-aircraft guns were pointed toward the United Kingdom and it was Reich policy to keep all peacetime lights on at night. When the DB-3s flew over the capital, they were largely misidentified as errant Luftwaffe aircraft and sent signals asking them who they were. Five bombers were able to reach their targets and put the fear of the proletariat into the Reich. Not that it had much material effect, as subsequent raids quickly found themselves running into fully alerted anti-aircraft, and as many as eighteen bombers would be lost in a night until the Wehrmacht conquered Osel in August 1941 and the raids ended. Still, the raids boosted Soviet morale at a time when any support was desperately needed. 

2. Harper’s Ferry Raid 

20 men versus the institution of slavery in the United States. That was what John Brown could bring to muster against the Virginian Harper’s Ferry Armory on October 16, 1859, with the intent of arming a slave revolt that would spread throughout the South. Brown hoped that if he seized the thousands of small arms in the armory, enough of the 18,000 slaves in surrounding counties would rise up that they could overwhelm all militias and marines sent to put them back down. Both Frederick Douglass and Harriet Tubman had denounced the plan, with Douglass warning Brown he was leading his insurrectionists into a “perfect trap.” 

While the raiders did seize control of the armory and took eleven hostages, one of the first people they killed was a free black porter named Hayward Shepherd, which likely contributed to the fact far fewer slaves rose up in revolt than Brown needed. Over the next two days, Brown’s men were surrounded by thousands of militia members and several attempts to negotiate their release resulted in an abolitionist being shot dead. By October 18, a force of 90 marines broke into the armory and captured the remaining raiders in less than three minutes. Brown and other captured raiders would be put to death on December 2, 1859. Only five of the original group lived to tell the tale.   

Once again, short-term failure turned out to be a long-term triumph because of how Brown conducted himself through his trial and execution. His belief that his martyrdom would provide the impetus needed to cleanse the sins of the nation with blood left him fearless in the face of the gallows. Millions throughout the nation were inspired on both ends of the political spectrum, with even many slavery supporters offering him a grudging respect. No less than John Wilkes Booth, who witnessed the execution, would despite his admiration for the Confederacy write admiringly of Brown for years after his execution and say that Lincoln wasn’t fit to follow in the footsteps of that “rugged old hero.” 

1. Grierson’s Raid

On April 17, 1863, Union soldiers under Ulysses S. Grant were in a tight spot. They had just run the guns at Vicksburg, Mississippi, and were to a significant degree cut off from their supply lines. If the Confederate troops under General John Pemberton moved swiftly, they could catch Grant with his back to the Mississippi and potentially destroy him as they almost did at Shiloh the year before. But Confederate eyes were largely turned away, following a force of 1,700 cavalrymen under the command of Benjamin Grierson. Their ride would take them from Tennessee, through Mississippi, and down to Louisiana. 

They would ultimately ride 600 miles in sixteen days while the raiders were outnumbered more than 20 to 1, inflicting hundreds of casualties while suffering less than 20 themselves. More importantly, they kept the Confederate Army too occupied to move south against Grant and thus allowed the Vicksburg victory that essentially did more than anything to doom the Confederacy. Pretty good results for a raid led by a man who before the war was a music teacher that despised horses. 

Dustin Koski cowrote the post-apocalyptic supernatural comedy Return of the Living with Jonathan “Bogleech” Wojcik.