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Gideon Pillow (1806-1878) -

Pillow was a US Army major general of volunteers during the Mexican–American War and Confederate brigadier general in the American Civil War. He famously failed to exploit a temporary breakthrough of Union lines, which might have allowed the Confederate garrison of Fort Donelson to escape at the Battle of Fort Donelson in 1862.

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Gideon Pillow (1806-1878) -

Pillow also commanded a brigade at the Battle of Stones River in 1863, where he performed poorly. Bankrupt after the war, Pillow recovered financially and resumed a successful legal career.

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Lloyd Fredendall (1883-1963) -

The Battle of Kasserine Pass in February 1943 is widely remembered as the first clash between American and German forces. It's also the battle where Major General Lloyd Fredendall went down in the history books for all the wrong reasons.

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Lloyd Fredendall (1883-1963) -

According to multiple accounts, the American soldiers had no training in fighting as a cohesive unit. Fredendall also botched a prime opportunity to counterattack by delaying the order, giving German forces time to fall back after already doing heaps of damage. After the disastrous battle, Fredendall returned to the US, where he remained for the duration of the war.

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Francisco Solano López (1827-1870) -

López was a military officer who served as President of Paraguay between 1862 and 1870, of which he served mostly during the Paraguayan War. By December 1864 Paraguay was at war with Brazil and, when Argentina denied a request for the transit of a Paraguayan army across its territory, López declared war on that country as well.

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Francisco Solano López (1827-1870) -

Argentina, Brazil, and the Brazilian puppet government in Uruguay formed an alliance in 1865, and declared war on Paraguay. This devastated Paraguay, and around 90% of Paraguay's fighting-age men perished. On top of that, López ordered the execution of hundreds of people, including some of his own family members. He was killed in combat on March 1, 1870.

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Douglas Haig (1861-1928) -

Haig was a senior officer of the British Army during the World War I, and had largely dismissed the effect of the machine gun on the battlefield. So, on July 1, 1916, Haig ordered his men to go over the top at the First Battle of the Somme, and 20,000 of them died almost immediately. Ultimately, a total of 60,000 British casualties was recorded on the first day of the attack. 

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Douglas Haig (1861-1928) -

However, Haig didn't change tactics, and continued to view attrition as the most effective strategy. In the end, the British lost some 420,000 men at the Somme. Haig lost another 275,000 troops at the battle of Passchendaele. After the war, the phrase "lions led by donkeys" came to be associated with the British Army for obvious reasons.

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William Hull (1753-1825) -

Hull fought in the American Revolutionary War and was appointed as Governor of Michigan Territory from 1805 to 1813. However, he is most widely remembered as the general in the War of 1812 who surrendered Fort Detroit to the British on August 16, 1812, following the Siege of Detroit.

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William Hull (1753-1825) -

After the battle, Hull was taken prisoner by the British and was court-martialed upon his return to the US. He was found guilty on 11 counts, and only the intervention by President James Madison spared him from execution.

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Erich Ludendorff (1865-1937) -

During World War I, German general Ludendorff was responsible for changing the Schlieffen Plan, Germany's overall battle plan for fighting a two-front war, which had weakened the attacking army on the Western Front. Ludendorff's offensive failed for a number of reasons, one being that he sent too many men into France. This meant he didn't have any reserves or replacement troops.

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Erich Ludendorff (1865-1937) -

Later as the harsh terms of the Treaty of Versailles crippled Germany, Ludendorff effectively hoodwinked  the nation by propagating the belief that he and his armies had been undefeated on the battlefield. He then served as a National Socialist member of the German parliament before becoming deeply involved with mysticism. 

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George McClellan (1826-1885) -

McClellan was an American military officer who served as the 24th governor of New Jersey. During the American Civil War, he organized and led the Union Army in the Peninsula campaign in southeastern Virginia, which unraveled after the Seven Days Battles. 

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George McClellan (1826-1885) -

McClellan also failed to decisively defeat Robert E. Lee's Confederate Army at the Battle of Antietam. Frustrated by McClellan's cautious tactics, President Lincoln removed him from command.

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Maxime Weygand (1867-1965) -

Weygand was a French military commander in World War I. In 1940, Weygand was recalled for active duty and assumed command of the French Army during the German invasion of World War II. 

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Maxime Weygand (1867-1965) -

Following a series of military setbacks, Weygand advised an armistice and France subsequently capitulated. He joined Philippe Pétain's Vichy regime as Minister for Defense and served until September 1940, when he was appointed Delegate-General in French North Africa. While in this position, he was noted for exceptionally harsh implementation of German Anti-Semitic policies. 

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Bernard Montgomery (1887-1976) -

In the fall of 1944, after the success of the D-Day landings in June, the German army was on the back foot. Montgomery was the senior British Army officer for Allied forces tasked with retaking important territory in the Netherlands. This would allow them direct access across the River Rhine into northern German territory.

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Bernard Montgomery (1887-1976) -

While Allied troops did take Dutch territory such as Eindhoven from the Germans, the operation's main objective failed after the Allies effectively lost the Battle of Arnhem. Overall, Montgomery's plan was too optimistic. 

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Pierre-Charles Villeneuve (1763-1806) -

In 1804, French naval officer Pierre-Charles Villeneuve was placed in charge of the French fleet at Toulon and tasked with drawing the British fleet under Horatio Nelson to the Caribbean. Villeneuve was then to return in secret and help establish naval dominance of the English Channel. Disobeying orders, he sailed for Cádiz instead, allowing Nelson's fleet time to return and effectively ruin Napoleon's plans for a cross-Channel invasion.

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Pierre-Charles Villeneuve (1763-1806) -

Nelson's victory at the Battle of Trafalgar established British supremacy on the high seas for more than a century. Villeneuve lost 20 ships, while Nelson lost none. After being taken prisoner by the British, Villeneuve was released but committed suicide rather than face Napoleon.

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Douglas MacArthur (1880-1964) -

During World War II, MacArthur served as General of the Army for the US, as well as a field marshal to the Philippine Army. On December 8, 1941, hours after they attacked Pearl Harbor, the Japanese targeted Clark Field, a US airbase in the Philippines. Despite being informed about Pearl Harbor, MacArthur severely delayed mobilizing Clark Field's aircraft for a counterattack. 

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Douglas MacArthur (1880-1964) -

And when the Japanese attacked, the American bombers were still grounded, which was another victory for the Japanese. The Philippines would eventually be overrun early in the war, with President Franklin Roosevelt ordering MacArthur to leave for Australia. The general left behind thousands of American and Filipino troops, who after being captured endured what is now notoriously known as the Bataan Death March. 

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Antonio López de Santa Anna (1794-1876) -

Mexican general Antonio López de Santa Anna's rise to power was characterized by betrayal of his allies. After his defeat by the Texans at the Battle of San Jacinto, Santa Anna was captured. He effectively pledged to become an agent for the US but found that he had been deposed upon his return to Mexico. He served as the eighth president of Mexico multiple times between 1833 and 1855. 

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Antonio López de Santa Anna (1794-1876) -

Driven into exile in Cuba in 1845, he contacted US President James K. Polk upon the outbreak of war between Mexico and the US, and offered to become an agent. He was sent to Mexico and upon his arrival went back on his word, instead taking charge of the Mexican troops. Defeated by the US forces, Santa Anna was again driven into exile. 

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Erwin Rommel (1891-1944) -

German Field Marshal Erwin Rommel was known as the "Desert Fox" due to his military process in North Africa. However, not even his greatest achievements amounted to much in the grand scheme of Axis strategy. 

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Erwin Rommel (1891-1944) -

Even at the height of Rommel's success in North Africa, he and his forces were never in the ideal position, often reliant on captured British supplies and vehicles. Overall, Rommel was never successful when it came to logistics.

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Maurice Gamelin (1872-1958) -

Less than a year after invading Poland, Germany launched a campaign against France, Luxembourg, the Netherlands, and Belgium. The offensive was well-coordinated, and succeeded in just over six weeks. General Maurice Gustave Gamelin, France's commander-in-chief, took little action to stop it.

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Maurice Gamelin (1872-1958) -

In the end, Gamelin's planning for the initial stages of the Western Front were inadequate. He 
predicted that Belgium would be the enemy's initial focus and placed his best troops there, but left the Ardennes Forest undefended. The Germans unleashed an offensive through the forest, catching the Allies off guard.

Sources: (Britannica) (Grunge) 

See also: 

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