Crossing the mountain passes in the Guadarrama range was always a dangerous business; since the time of the surrender of Madrid to Alfonso VI, there were bands of Toledo Muslims who made their living by pillaging throughout the region. In 1273, Alfonso X granted special privileges to the medieval hostels which provided shelter for travellers and protected them from the gangs of Moors which still remained at large in the area.
The smallholders of Segovia would track down the brigands and dispense summary justice by means of the noose and the knife; a reminder of this grisly custom can be found in the names 'Puente del Perdón' (Bridge of Pardon) and the 'Casa de la Horca' (House of the Gallows) near el Paular.
The Latin chronicles documenting the reign of Henry IV of Castile make mention of Barrasa, a sinister character who ambushed travellers as they passed through the Guadarrama mountains, and not only robbed them of everything they carried, but also disfigured their faces.
In the late 18th century, the band of Manuel Rodríguez, who was known as 'the king of men', and his second-in-command, 'Cabeza Gorda', or 'fat head', roamed this area with total impunity. They were active around the Puerto de Navacerrada mountain pass, and used to hide around the area of el Paular or in the crests of the Siete Picos. They were finally rounded up in 1792 by more than 400 men including troops and countrymen, and despite putting up a fierce fight, they were ultimately defeated.
From the early 19th century we learn about the crimes of 'Chorra al aire', a bandit veteran of the Peninsular War, who began by capturing French couriers on the roads around Burgos and ended up hijacking stagecoaches. In 1816, after simply stealing a few sides of bacon from some ploughmen in the Alto de los Leones pass, he was pursued and run to ground near el Escorial where he was arrested, taken to Madrid and executed.
In 1838, 'la Tuerta' (the one-eyed woman), a female horse dealer by trade who dressed as a man and ambushed travellers passing through the Alto de los Leones, told her story to the English traveller George Borrow, who recounted her adventures in his book 'The Gypsies in Spain'.
Pablo Santos, whose refuge was around the Cancho Centeno crag in la Pedriza, specialised in robbing stagecoaches. His most notorious exploits included the ambush of the Madrid-Bayonne mail coach (known as the 'Mala de Francia' from the mispronunciation of the English word 'mail'), and the kidnapping of the son of a wealthy woman from El Boalo, Braulia del Valle, who was obliged to pay a substantial ransom. Pablo Santos died in a vengeance killing with his second-in-command, Isidro 'the Man from Torrelodones', over differences which arose while sharing out the booty from a robbery.
Francisco de Villena, known as Paco 'the Tailor' roamed these hills after escaping from the Saladero gaol in Madrid; his most famous exploit was the kidnapping of the children of the Marquis of Gaviria in 1839, using the tactic of picking them up at their school gates in Madrid disguised as the Marquis's coachman, then taking them to la Pedriza, where he made his hiding place. He had a shepherd from Manzanares take a letter to the Marquis demanding a ransom of three thousand ounces of gold in exchange for the children's lives. Before the ransom was paid, the gang of bandits was rounded up near the Tolmo cliff by soldiers from the Reina Gobernadora Regiment, guided there by the manager of the paper factory in Manzanares, who knew the area well. 'The Tailor' managed to escape, but one year later he was discovered in Madrid as he strolled carelessly around the Rastro market, and was promptly arrested, imprisoned and sentenced to death. The execution was carried out at the usual gallows on the Paseo de Pontones avenue, near the Puerta de Toledo.
In 1854, the creation of the Civil Guard and the subsequent use of the telegraph gradually meant that these robberies no longer went unpunished.
Fernando Delgado Sanz, known as the 'one-eyed man of Pirón', was the last great outlaw of the region. He started his career as a cattle rustler, stealing cattle which he then sold to dealers passing through the region and traders at the fairs of Pinilla and Buitrago, and later joined forces with other ruffians to attack travellers on the roads in the Lozoya Valley. He was not given to murder, however, and he is only known to have killed one man: an accomplice, to settle a score.
His most notorious feat took place in 1880 when he robbed the church of Tenzuela in Segovia, gaining entry by climbing up its tall tower. This exploit was published in the Madrid newspapers and made him famous. He managed to elude the authorities for more than 15 years, and cunningly slipping out of ambushes, hiding in inaccessible places, sleeping under rocks and in abandoned shepherds' huts. He was arrested in Rascafria after being turned in by a churchwarden, taken to the gaol in Segovia, whence he escaped, and was finally arrested in 1882 by the Civil Guard, sentenced to life imprisonment and died in 1914. He went down in history with the dubious honour of being the last bandit in the Guadarrama mountains.