Niccolo Sfondrati was born near Milan to a solid family. His father, formerly a Milanese senator, was made a cardinal in 1544 following the death of his wife. Niccolo would eventually follow suit, but not before being made a bishop in 1560 and assisting at the Council of Trent. Though barely in his mid-20s, Niccolo was already pious, conscientious, and in every way a student of his mentor, St. Charles Borromeo. As a cardinal, Niccolo was a close friend and admirer of the great St. Philip Neri, founder of the Congregation of the Oratory, who would outlive Niccolo by just four years.

Pope Gregory XIV was elected after several months of deliberations. Having never sought the office for himself, he supposedly said to his fellow cardinals, “God forgive you! What have you done?” Gregory first tried to reconcile with the Protestant heir to the French throne, Henry of Navarre. Henry, whom Sixtus V had declared a heretic in 1585, was asked to become Catholic before being crowned king, given that France remained a primarily Catholic country. Henry initially said, “Mmkay,” to get in the pope's good graces, but his lack of intent to fulfill the promise soon became clear. Gregory renewed Henry’s excommunication and sided instead with Henry’s French opposition. Gregory’s other significant act as pope was demanding reparation and release for all Philippine and other island slaves being kept by Europeans in the New World.  Gregory, who was already ill at his election, died on October 16, 1591 after a papacy of just 10 months.

Fun Fact: In his papal bull Cogit nos (“Compels us…”), released March 21, 1591, Pope Gregory XIV said, “May the odds be never in your favor,” and forbade the practice of betting on papal elections, the duration of a papacy, or the naming of cardinals -- on pain of excommunication, no less.

Giovanni Antonio Facchinetti, who'd been trained as a lawyer in Bologna, lived in service to the Church for most of his adult life. He was first employed by Cardinal Farnese (Pope Paul III) to manage the Archdiocese of Avignon in 1544. Giovanni was made Bishop of Nicastro in 1560 and was present at the Council of Trent a few years later. St. Pius V sent him to Venice in 1566, where he played a crucial part in the Catholic alliance against the Turks, which led to victory in the Battle of Lepanto in 1571. Giovanni was made Latin Patriarch of Jerusalem in 1575, then received his red hat in 1583. During Gregory XIV’s short reign, he managed most papal business for the ailing pope.

Pope Innocent IX was the choice of the pro-Spanish party of cardinals, being elected after just three rounds of voting. It made sense, then, that Innocent favored King Philip II’s effort to squash the King Henry IV of France (the same guy deemed a heretic by Gregory XIV). He held a single consistory to name new cardinals, elevating two men just weeks before his death. Innocent was also an avid writer, but died before his works on theology and philosophy were published. Innocent IX was pope for barely two months, dying the morning of December 30, 1591.