Giovanni Leonardo Di Bona, born in 1542 in Cutro, Calabria, emerged as a prominent figure in the world of chess and law during the Renaissance. His legal studies in Rome laid the foundation for a life that would intertwine intellectual pursuits with the strategic complexities of chess.
In 1560, Leonardo faced a significant challenge when he lost a match to the renowned Ruy López in Rome. This setback did not deter him; instead, it propelled him into a series of travels across Europe from 1566 to 1572, where he showcased his chess prowess in cities like Rome, Genoa, Marseille, and Barcelona. His matches against Paolo Boi were particularly notable, as both players were considered equals in skill.
Leonardo's career reached a pinnacle in 1575 when he, alongside fellow chess master Guilio Cesare Polerio, triumphed in the first known international master tournament held in Madrid. This victory solidified his reputation as the strongest chess master of his time. Following this achievement, he and Boi ventured to Lisbon, where they successfully challenged Il Moro, the esteemed chess champion of King Don Sebastian of Portugal.
After his victories, Leonardo sought to honor his hometown of Cutro by requesting a tax exemption, affectionately dubbing it the 'City of Chess.' His triumphs earned him the title of 'Il Cavaliere errante' from King Don Sebastian, leading him back to Italy, where he settled in Naples and became the chess master for the Prince of Bisignano. Unlike many of his contemporaries, Leonardo was known for his slow, positional style of play, favoring sound tactics over aggressive attacks.