Win the Battle, Lose the War: 6 of History’s Costliest Military Victories

Depiction of the Battle of Asculum. Pinterest

A pyrrhic victory occurs when you achieve a win at such a high cost that it is virtually a defeat. While you are victorious in the traditional sense, the heavy toll incurred eliminates the spoils associated with winning. The term is named after King Pyrrhus of Epirus who defeated the Romans in two major battles (Heraclea and Asculum) in 280 BC and 279 BC respectively.

However, he suffered such heavy losses that his campaign ended in failure. After Asculum, he reportedly said that one more victory like that would result in him returning to Epirus alone. In this article, I will look at 6 of the most famous ‘win but actually lose’ scenarios in history including the original Pyrrhic victory.

King Pyrrhus. Weapons and Warfare

1 – Battle of Asculum (279 BC)

Pyrrhus was the King of Epirus and became something of an inspiration to the Carthaginian general Hannibal. He took up arms against Rome after answering an appeal from the Greek city of Tarentum as they fought against the Roman Republic. Although he was an excellent commander by all accounts and enjoyed victories against the enemy, the losses he suffered during the Pyrrhic Wars (280-275 BC) were so great that he was unable to follow up on his wins in the long term.

Pyrrhus defeated the Romans at the Battle of Heraclea in 280 BC but lost thousands of men in the process. Both sides geared up for more fighting, and in the following year the Battle of Asculum took place. It was an even more brutal affair than Heraclea as both sides had enormous armies. Indeed, they were evenly matched with approximately 70,000 infantry and 8,000 cavalry apiece. Pyrrhus also had 19 war elephants.

Ancient historians disagree as to the duration of the battle. While Plutarch said it lasted two days, Cassius Dio and Dionysius wrote that it took place over a single day. Regardless, it was a bloody affair, and while the losses suffered by both sides paled into comparison with casualties during the Second Punic War some 60 years later, the losses were heavy enough to cripple Epirus and cause its king to declare that another such battle would ruin him.

Pyrrhus knew that he couldn’t win a war against Rome, so he answered another appeal; this time from Greek city states in eastern and southern Sicily who needed help against Carthage. He campaigned for three years but angered his southern Italian allies who believed he abandoned them. After treating Greek city states poorly in his quest for more manpower, Pyrrhus had to deal with a revolt and returned to southern Italy. Eventually, he fought Rome one last time at the Battle of Beneventum in 275 BC and suffered defeat. The king died in a skirmish at Argos in 272 BC.


  • Eto

    Jackson was NOT killed that night. He was wounded, and had to have his arm amputated. He died of pneumonia several days later.

    • Russ7777

      I think you are nit-picking. He was mortally wounded, and his services were lost to the South for all time.

      • Paul Hatfield

        He was actually making progress in his recovery, but pneumonia set in – probably owing to the trauma is body suffered. That’s what did him in. Jackson’s surgeon would later establish what would become the Medical College of Virginia (part of Virginia Commonwealth University in Richmond) after the war…

  • Weston Jurney

    Somehow they don’t remember Pearl Harbor?

    • Mark Augustyniak

      Pear Harbor does not fit the definition of a Pyrrhic Victory. Japan’s losses in the attack were insignificant. It ultimately failed at its objective to cripple US naval might, but casualties were about 60 to 1 in their favor.

      • Bill Came

        You beat me to it.

      • Alexbensky

        They lost twenty-nine aircraft; others were damaged and had to be written off. I don’t recall the exactly number off hand but they destroyed, I think at least 150, as well as sinking a number of battleships. It was a stunning tactical victory.

        Strategic disaster, but a tactical win.

        • oatwillie

          They would have been better off burning the fuel farm and destroying the repair shops and submarine facilities.

          • Daniel Vondermock

            Yes they would have. The loss the Japanese suffered at Lrarl Harbor was just that a strategic one.

        • Will

          And it wouldn’t have been a strategic disaster of they had won Coral Sea or Midway.

          • Stan Allan

            Even if they had won either, ultimately they would have lost. There was simply no way for them to match our material war output, or manpower. It would have taken failure after failure on Americas’
            part to lose, and that is a very unlikely scenario.

    • John Steudl

      Was that a battle seems more a terrorist attack.

      • Russ7777

        Given the fact that it was a military strike against a military target, I would call it a battle.

        • Lucas Winsor

          Considering that they specifically targeted civilians along with military targets, you really can’t say that.

    • Dan Zervos

      I was thinking the Tet Offensive. The Tet Offensive was a massive victory for the USA and allies. The Viet Cong were finished and the North suffered so many losses it took a couple of years to regroup. However the Communists won a propaganda victory that lead to the Democrat Party in the US writing off South Vietnam.

      • Michael Fromholt

        It was a republican presidency(Nixon), and they may have sabotaged the peace negotiations that were underway under Johnson.

  • Russ7777

    The loss of Jackson was the single greatest loss to the South at Chancellorsville. I personally think if Jackson had not been wounded, and had been at Gettysburg, the South would have won at Gettysburg.

    • Curt Hauser

      It doesn’t matter if the south would have won Gettysburg. The north couldn’t allow the south to leave, period. Therefore the north would have continued the slash and burn policy and ground the south into a pile of ash. Loosing was the best thing the south ever did for itself

      • UnreconstructedRebel

        If Jackson had been with Lee, the South would have won Gettyburg and Lee’s army would have occupied Wash DC and dictated the terms of a peace treaty ending the war.

        • Daniel Vondermock

          Even with a victory at Gettysburg and a occupation of Washington the North Would not have been backed up to a negotiated peace. Lee’s Army, with a win or a loss at gettsburg, would not have been able to take Washington.

        • makkabee

          Keep on fantasizing.

  • Will

    In manpower terms I’d put Franklin for the Confederacy.

  • Richard Allen

    The civil war was lost by the South before the first shot was fired. Lee knew it, you can see it in his early war correspondence – even the Confederate currency refers to a treaty of peace rather than vanquishing the North. The most the Confederate leadership hoped for was a peace treaty with the Union. In any event, the Confederate leadership all knew the South lacked the resources to win the war. Every battle the Confederates fought moved them closer to defeat. Each battle steeled the Union’s resolve and further bled the Confederacy. It was a Pyrrhic war for the South as was every battle for the Confederacy.

    • Dr. Todd Collier

      The South never intended to “vanquish” the North. The strategy was always about not losing long enough to force a political settlement. Mr. Lincoln’s opposing strategy was to bring matters to a head as quickly as possible, hence the disasters in Virginia from ’61-63.

  • Oncle

    I kept waiting to see thermopylae, never came up, it would have been number 1 on my list…

  • Serena Vann

    sad no matter who won or lost!!