The frescoes in the lower church of the Sacro Speco at Subiaco closed the complex architectural history which during the 13th century, from the time of Pope Innocent III (1198–1216), saw the growth of the sanctuary created around the cave where St. Benedict of Norcia retired in the early 6th century.The cycle with stories of the saint, signed by Magister Conxolus, has so far been considered by the critics only for its stylistic and formal characters in connection with paintings in Rome and Assisi during the second half of the 13th century. Starting from these acquisitions, the paper will analyse the selection and the display of the stories — one of the first cycle about the life of Benedict on such a large scale in the Middle ages, — their iconography and their reading direction in relation to the Holy stairs leading to the cave and in the broader context of the debate on new religious orders after the Council of Lyons (1274). From this perspective, the parallel with the friars and, in particular, with the Franciscans who, just few years before, had glorified their founder in the famous basilica of Assisi, seems once again significant. The similarities with the pictorial cycle of the upper church of San Francesco, in fact, seem to go beyond the stylistic point of contact already identified by the critics to include broader issues. The foundation of two churches in Subiaco and the decoration of the lower one with the celebration of the founder at the time shortly after the frescoes in Assisi, cannot fail to take account of comparison — and perhaps of antagonism — that existed between two types of common life entirely different: the traditional monasticism and the new orders.