Yes during the Middle Ages, and Renaissance especially, the papacy fell on evil times. Just one example: Alexander VI, the Borgia pope, was an ambitious power player who held aspirations of establishing papal control over all of Italy and making the papacy a family dynasty. He had a broad swath of the peninsula, in the Papal States, and had the wherewithal to hire mercenary armies to impose his will on uncooperative rivals. He supported his son, Cesare, in establishing a duchy in Romagna, which was to be a major addition to Vatican holdings. It all fell apart with Alexander’s death, although the Papal states endured into modern times.
Alexander VI is generally considered to be one of the worst of the popes. Ironically, one of his descendants was St. Francis Borgia, one of the early Jesuits, who was a widower when he joined the Jesuits. Catherine of Braganza, the wife of King Charles II of England, was a descendant of St. Francis Borgia and thus of Pope Alexander VI.