[3]Dan appears first in the records leading a contingent sent by his uncle Mircea I to assist Musa Celebi in taking Adrianople during the Ottoman civil war in 1411.

[4] The Ottomans defeated Michael in 1419, forcing him to pay tribute and to cede Giurgiu and other fortresses along the Danube to them.

[5] However, Ottoman troops joined Dan, enabling him to defeat Michael and his Hungarian allies in the summer of 1420.

[citation needed] The Ottomans were invading in an effort to place Radu II back on the throne.

In 1425, he again defeated the Ottomans,[citation needed] winning an important victory in a battle that was the first recorded mention of Wallachia using mercenaries in their army.

However, his son lacked the military ability of his father and would lose the throne within a year to Vlad Dracul.