In 1489, Theodore was granted the small island of Cranae by the Venetian government, but he soon ceded it to another family. In the autumn of 1495, he was present at a siege of Novara, where the Venetians attempted to take the city from France. In March 1496, Theodore was one of the "stratioti" who accompanied Venetian naval captain Domenico Malipiero in a campaign in Savona. In 1500 he partook in the Siege of the Castle of Saint George on the island of Cephalonia. In December 1502, Theodore was captured at Canosa di Puglia by French troops, though he was soon freed. In February 1503, he was fighting alongside other "stratioti" in Calabria. In August 1511 he was stationed as a guard at Treviso, and from 1511 to 1512 he is recorded as travelling around Italy, serving as a guard and scout. Theodore was taken captive at the Battle of La Motta (7 October 1513), but was released at the end of the month.