He soon left on a raiding expedition with the warlord Odysseas Androutsos, who controlled much of Eastern Greece. Trelawny thought highly of Odysseas, describing him as a brother and comparing him to George Washington and Simón Bolívar. During this time Trelawny commanded a group of twenty-five Albanian soldiers. In the winter of 1823–24, Odysseas and his men fought several battles with the Turks and destroyed villages in the Euboea region. Trelawny lobbied Byron to send them more arms, but Byron decided to wait before shipping any to consider the political implications. Some have called into question the effectiveness of Odysseas' campaign and many view Byron's delay as a polite refusal.