Battle of Villalar The Battle of Villalar was a battle in the Revolt of the Comuneros fought on April 23 , 1521 near the town of Villalar in Valladolid province , Spain . The royalist supporters of King Charles I won a crushing victory over the comuneros rebels . Three of the most important rebel leaders were captured , Juan de Padilla , Juan Bravo , and Francisco Maldonado . They were executed the next day , effectively ending armed resistance to Charles I . Background . Maneuvers in March and April 1521 . In late March 1521 , the royalist side moved to combine their armies and threaten Torrelobatón , a rebel stronghold . The Constable of Castile began to move his troops ( including soldiers recently transferred from the defense of Navarre ) southwest from Burgos to meet with the Admiral ' s forces near Tordesillas . This was possible due to the comunero - aligned Count of Salvatierra ' s force being caught up in the siege of Medina de Pomar ; the Count ' s forces had previously been enough of a threat to force the Constable to maintain a large army to defend Burgos . The Constable ' s army was approximately 3 , 000 infantry , 600 cavalry , 2 cannon s , 2 culverin , and 5 light artillery pieces . His army took up positions in Becerril de Campos , near Palencia . Meanwhile , the comuneros reinforced their troops at Torrelobatón , which was far less secure than the comuneros preferred . Their forces were suffering from desertions , and the presence of royalist artillery would make Torrelobatón ' s castle vulnerable . They had two strategic possibilities : prevent the Constable and Admiral from united their forces by striking at the Constable while he was still on the field , or else low - level harrying operations to try to slow the Constable down . The comuneros did neither , and thus allowed the Constable to approach nearly unchecked . The commander of the comunero armies , Juan de Padilla , considered withdrawing to Toro to seek reinforcements in early April , but wavered . He delayed his decision until the early hours of April 23 , losing considerable time and allowing the royalists to unite their forces in Peñaflor . Battle . The Royalist army pursued the Comuneros . As had been the case through most of the war , Royalists had a strong advantage in cavalry , with their army consisting of 6 , 000 infantry and 2 , 400 cavalry against Padilla ' s 7 , 000 infantry and 400 cavalry . Heavy rain slowed Padilla ' s infantry more than the royalist cavalry and rendered the primitive firearms of the rebels ' 1 , 000 arquebusiers nearly useless . Padilla hoped to reach the relative safety of Toro and the heights of Vega de Valdetronco , but his infantry was too slow . He gave battle with the harrying royalist cavalry at the town of Villalar . Comuneros set up their artillery to try to blunt the cavalry charge , but this failed . According to some reports , the artillery did more damage to the comuneros than the royalist cavalry . Sources differ on the reasons behind this . According to the account of Pedro de Alcocer ( a friend of the Padillas ) , the Comuneros were betrayed ; the artillery and some 300 soldiers had been bought off by the royalists prior to the battle , and switched sides . The artillery intentionally fired high and destroyed their powder . A slightly more subdued theory blames the rain for the ineffectiveness of the Comunero artillery . Finally , it is possible that in the heat of the battle , the artillerymen simply panicked and made mistakes . The cavalry charges scattered the rebel ranks thus ending the battle and becoming a slaughter . There were an estimated 500 – 1 , 000 rebel casualties and many desertions . The three most important leaders of the rebellion were captured : Juan de Padilla , Juan Bravo , and Francisco Maldonado . They were beheaded the next morning in the Plaza of Villalar , in front of a large portion of the Royalist noblemen . The remains of the rebel army at Villalar fragmented , with some attempting to join Acuña ' s army near Toledo and others fleeing to Portugal . The rebellion was struck a crippling blow . Aftermath . Demoralized , and without leaders or an army , the rebel cities of Old Castile soon surrendered to the Constable ' s armies . It took slightly longer for the Constable ' s armies to march south to New Castile and retake Madrid . They likely would have taken Toledo as well , but a French invasion of Spanish - controlled Navarre meant that the army needed to immediately be recalled north to fight the French and Navarrese . As a result , the Revolt stretched out several months more , with Toledo resisting until October . Legacy . The Battle of Villalar would later be claimed by Spanish liberals as the blow that extinguished Castilian liberties in favor of autocratic Spanish monarchy . This view started in the 1820s , as Juan Martín Díez " " El Empecinado " " , a nationalistic liberal military leader during the Peninsular War , led an expedition to find and exhume the remains of the three Castilian leaders executed in 1521 . Later , some city councils called for celebrations at Villalar in the 1920s . After the end of Franco ' s dictatorship , this view became more generalized . The autonomous community of Castile and León made April 23 the official holiday of Castile and León Day in 1986 , although it had been popularly celebrated since 1976 . It is celebrated yearly at Villalar , which has since the Second Spanish Republic renamed itself Villalar de los Comuneros , honouring the Castilian rebels .