1492, Loredan secured the election to one of the most distinguished offices of the Republic, that of Procurator of Saint Mark, which allowed him to rise to the political pinnacle of the state. On 3 May 1493 he was among the Governatori alle Entrate and from 1495 to 1501 he was continuously re-elected Savio del Consigli. In his capacity as procurator and also as Savio del Consigli, he was among the three designated by Doge Agostino Barbarigo, on 31 March 1495, to negotiate the alliance between Venice, Pope Alexander VI, Holy Roman Emperor Maximilian I of Habsburg, the Spanish rulers Ferdinand V and Isabella I and the Duke of Milan Ludovico Maria Sforza (Henry VII of England also joined), with the aim of countering the military operations of the King of France Charles VIII who had, almost without encountering resistance, entered Naples in February. The army of the League, led by the Marquis of Mantua Francesco II Gonzaga, in the Battle of Fornovo on 6 July forced the French army to withdraw from Italian territory. In October of the same year, Loredan signed the agreement for the conduct of Nicolò Orsini, count of Pitigliano, to the services of the Republic of Venice as captain-general of the land forces for a period of three to four years. In January 1497, Loredan, with the Savio di Terraferma Lodovico Venier, ratified the surrender of Taranto on behalf of the doge. On 11 July 1501, Loredan was appointed podestà in Cremona by the Senate, but he refused. On the death of Barbarigo (20 September 1501), Loredan was one of the designated candidates in the election of the new doge, which began on 27 September, and finished on 2 October with Loredan coming out first (with 27 votes in the sixth hand of the first ballot). The election was successful thanks to his and his wife's influential relations and the sudden death of the most popular opponent, the wealthy procurator Filippo Tron, son of Doge Nicolò Tron. The announcement was made by the procurator Nicolò Mocenigo and celebrated by the scholars, with numerous praises then given to the press. Dogeship War with the Ottomans At the time of his accession to the dogeship, Venice was engaged in the Second Ottoman–Venetian War, which had started in 1499. Loredan had lost his cousin Andrea Loredan, a naval officer, in the disastrous Battle of Zonchio, and the war