This article reinterprets four documents attributed to the artist Leonardo da Vinci. These documents include a drawing considered to be a Tuscan landscape with an inscribed date of August 5, 1473, a single double-sided page with drawings, writings, and a tensioning crossbow design dated 1478, a drawing of a hanged man dated 1479, and a letter written in Turkish to the Sultan of Istanbul dated circa 1502. If the Tuscan painter created these documents, he was pursuing an alternative career as a scientist. However, the information is incomplete and inaccurate. First, the landscape does not represent Tuscany. Instead, further research indicates that it is the depiction of a fortress in Crimea that relates to significant events occurring in the Ottoman arena between 1473 and 1475. Second, biographers have failed to show evidence that the Tuscan painter had military connections, raising the issue of a non-affiliation with any militia. Third, the sketch of a hanged man focuses an unexplained attention on the victim’s Turkish style of dress. Finally, a letter sent to Istanbul around 1502 claimed Leonardo was Genoese. Taking note of these points, a cumulative reading of the evidence shows that the man who crafted these documents originated from Caffa, a Genoese colony on the Black Sea that the Ottomans captured in 1475. Although this might sound speculative, further documents discussed in the final section indicate that Florence banished the Tuscan painter Leonardo da Vinci around 1477 and that he later died in Bologna in 1499. Therefore, this Tuscan Leonardo could not have written the Notebooks, and the man who died in France in 1519 could not have been him. The research adds a deeper understanding of Turkish influences in the documents and highlights how information gathered outside Europe can better explain them. The findings urge Western art historians to expand their research and to reconsider other authors.