The Jubilee, whose roots are embedded in the Scriptures (Leviticus 25:8-13), was established in 1300 as a response to 2 needs: reinforcing the centrality of the papacy & Rome, whose sanctity needed to compete with the relics brought back to the West during the Crusades, & providing pilgrims with a sacred destination in place of the now-inaccessible Holy Land. The event also offered the faithful an opportunity to intercede for the souls of the deceased through indulgences granted by the Church.  

The first Jubilee took place under Boniface VIII on Christmas Eve in 1299 & attracted a great influx of pilgrims, fueled by a millenarian climate inspired by the prophecies of Joachim of Fiore, who predicted the imminent end of times. The overwhelming participation astonished both the Pope & his contemporaries, with figures like Dante Alighieri & Giovanni Villani recording the event. However, the massive crowd led to numerous accidents, some fatal: to manage the flow of pilgrims, a new entrance was opened, and access to the bridge in front of Castel Sant’Angelo was restricted, as described by Dante in Inferno, Canto XVIII.  

During the Avignon Papacy, the event was altered, with the Jubilee moved forward to 1350, coinciding with the Black Death and an earthquake. In 1390, Clement VI decreed that a Jubilee should be held every 33 years, a period during which Rome, depopulated & competing with rival popes during the Western Schism, sought to reassert its significance.  

The Jubilee of 1400 was more successful, but in 1450, the traditional 50-year interval was reinstated. It was later reduced to 25 years in 1475 under Sixtus IV, who reserved indulgences exclusively for Rome to restore the city's prestige. To improve infrastructure, he commissioned the construction of a bridge over the Tiber after a tragic incident in which over 170 pilgrims lost their lives in a stampede triggered by the restless movements of a mule.  

The Jubilee of 1500 was a triumphant event, celebrated in the wake of the conquest of Constantinople & the victory of the Catholic Monarchs over Granada. In contrast, the 1525 Jubilee saw much lower participation due to the impact of the Lutheran Schism in 1517.