Quintus Servilius Caepio

This entire list could be populated with Roman commanders, but one manages to rise
above the rest with an ineptitude that defies logic. Marcus Licinius Crassus was a
self-aggrandizing opportunist who started a pointless war with the Parthians, and
Publius Quinctilius Varus lost three legions at Teutoburg Forest, but Proconsul
Quintus Servilius Caepio manages to top them both with his actions at the Battle of
Arausio. Consul Gnaeus Mallius Maximus was Caepio’s superior officer, but Caepio
refused to obey Maximus or even put his forces into a shared camp with him. While
Maximus was conducting negotiations with the Cimbri, a Germanic tribe that had
invaded the Roman province of Transalpine Gaul, Caepio rashly attacked the Cimbri
army on October 6, 105 BCE. The Cimbri destroyed Caepio’s force and, emboldened by
their success, marched on Maximus’s camp. Maximus managed to form up his men but to
no avail. The Romans lost an estimated 80,000 infantry and perhaps 40,000
auxiliaries and cavalry, numbers that dwarf the staggering totals at Cannae.
Although he managed to escape the battle unharmed, Caepio was stripped of his Roman
citizenship and exiled. Caepio reportedly lived out the remainder of his life in
luxury, however. Some 15,000 talents of gold (the so-called Gold of Tolosa) had
vanished under his watch, never to be recovered. Caepio may have been a terrible
general, but he was apparently an exceptional thief.

Gideon Pillow
Armchair historians often generalize that during the American Civil War, while the
Union held a clear advantage in material, the Confederacy could field superior
commanders. That may have been true in the east (the worst of the Union generals in
that theater rates his own entry on this list), but in the west it was a much
different affair. Outstanding commanders such as George H. Thomas, Phil Sheridan,
and William Tecumseh Sherman routinely bested their Confederate opponents. Ulysses
S. Grant made his Civil War debut at the Battle of Belmont against Confederate Gen.
Gideon Pillow. Pillow suffered slightly more casualties than Grant in the
engagement, which possibly makes the Battle of Belmont the high point of Pillow’s
military career. In a war that saw more than its share of unskilled politically
appointed generals, Pillow was arguably the worst on either side. He first
demonstrated his ineptitude during the Mexican-American War, where he had received
an appointment to the rank of major general from his friend Pres. James K. Polk.
After making a laughingstock of himself by ordering his men to entrench on the
wrong side of fortifications at Camargo, Pillow bungled his role at the Battle of
Cerro Gordo, making himself the low point of a resounding American victory. Not one
to let his own failings stand in the way of personal glory, Pillow submitted
fanciful accounts of his actions at the Battles of Contreras and Churubusco to
various newspapers, incurring the wrath of overall American commander Winfield
Scott. Pillow faced a court-martial for stealing a Mexican cannon and attempting to
spirit it home in his personal baggage, but Polk intervened to clear Pillow’s
record. Scott claimed that Pillow was ''the only person I have ever known who was
wholly indifferent in the choice between truth and falsehood.” When talk of
secession reached Pillow’s home state of Tennessee, he helped organize the state
militia and was appointed a brigadier general in the Confederate army. After his
performance at Belmont—a spectacular success by Pillow standards—he was tasked with
the defense of Fort Donelson, a key strongpoint on the Mississippi River. Grant had
encircled the fort. After an initial attack drove back Grant’s troops, Pillow
snatched defeat from the jaws of victory by retreating to the fort rather than
breaking through Union lines to Nashville. Pillow escaped during the night, leaving
Simon B. Buckner to surrender the fort and 15,000 Confederate troops. The loss of
Fort Donelson opened the door to Kentucky and Tennessee to Union forces and marked
the beginning of the end of Confederate resistance in the west.