He achieved literary fame thanks to the erotic comedy Chrysis, on the other hand church infamy – due to his participation in a faction actively opposed to Pope Eugene IV, of which he was a member as a secretary of the Antipope Felix V. At the age of 37 he took over the post of secretary and imperial poet of Emperor Frederick III, as well as a lecturer of antique poetry at the University of Vienna. He exhibited his broad interests and knowledge in the unfinished works Europe and Asia, in which apart from geography and cosmography he also touched on the subjects of traditions of individual nations living on both continents. At that time as Roberto Gervaso wrote, “he was a man only religious enough, not to arouse any doubts”. He enjoyed earthy pleasures, adored women and fathered a few children. He was ordained as a priest at the age of 40 and at the age of 53 he became pope.

Reportedly the decisive vote in his election was cast at the conclave, by a young, only twenty-seven year old, nephew of the previous pope – the head of the Vatican finances, Vice-Chancellor Rodrigo Borgia (the later Pope Alexander VI). Perhaps the cardinals present (only 18) in a prematurely aged, suffering from gout, kidney stone disease and chronic cough, humanist with deformed limbs, saw a guarantee of calm and passive reign. This was partly true. The pope spoke little, willingly went to the country, where in peace he could partake in his hobbies. In nepotism he was no different than his so often criticized predecessor. Posts, appanages, cardinalships and properties were handed out to the members of the Piccolomini family. The pope also understood human weaknesses and with permissiveness looked upon lack of morality among members of the clergy. Although his words are rather an evidence of powerlessness: “The people say that our life compromises of only delight, we gather money, we love luxury…., we walk around the city with chubby faces under red hats, but we do nothing in the defense of the faith. Many of the cardinals and members of the Curia, act in this way”.

The material monument of Pius II is the pope’s hometown of Corsignano, which he himself renamed Pienza. It was intended to be an ideal town, decorated and enlarged at his initiative (but unfinished). In Rome during his six-year pontificate (1458-1464), he did not do too much, and that which he funded was unfortunately lost. These were frescos which adorn the papal sleeping chambers completed by Pier della Francesca, which during the pontificate of Julius II gave way to the frescos of Raphael. At his initiative a three-story loggia in front of the enterance to the old Basilica of San Pietro in Vaticano was created, patterned on the ancient architecture (Colosseum), which disappeared during a reconstruction. Pius II also issued – a very useful for Rome – decree forbidding the widely used practice of taking apart ancient buildings and using them as building material. He also supported, as was fit for an enthusiast of antique culture, archeological research and sponsored a new translation of the works of Homer.

Despite the fact, that the pope still partook in his literary hobbies, he did fulfill the responsibilities of the bishop of Rome with care. He severely spoke out against the Hussites in Bohemia, while his great ambition was to organize a crusade against the Turks, to which he actively encouraged all European rulers. He preached and wrote fiery speeches about united Christian Europe, which unfortunately fell on deaf ears. Seeing that use of force was not a solution, he changed tactics. He wrote a letter to the sultan, encouraging him in this worthy of a true humanist way to convert to Christianity: “We shall appoint You as the Emperor of the Greeks and the Orient and what you have now obtained by violence and hold unjustly, will be in your possession by right. Oh what glorious peace would then prevail! The golden age of Augustus sung by the poets would return”. When he did not receive a positive reply the pope returned to his plans of organizing a crusade against the infidels. The congress in Ancona which was to be the crowning moment of his efforts, and where a united papal fleet with him at the helm was to meet, along with the Venetian one (late due to the plague – ended with the death of the recently arrived pontifex.

The body of Pius II was taken to Rome and laid to rest in St. Andrew’s Chapel in St. Peter’s Basilica. The pope’s nephew, Cardinal Francesco Piccolomini, erected for him an enormous, multi-level tombstone, which in 1608 was transferred to the newly built Church of Sant’Andrea della Valle, where it can still be admired today.