On 2 or 6 September 1442 an army commanded by Şehabeddin and sixteen "sanjakbeys" subordinated to him, sent by sultan Murad II sent to Wallachia to kill Vlad II Dracul, was heavily defeated near Ialomița River by the forces led by Janos Hunyadi. After this defeat Şehabeddin was dismissed from the position of "beylerbey" of Rumelia. In 1444 Şehabeddin appeared as commander of the forces that fought against Orhan, the challenger of the sultan's throne and again as "beylerbey" of Rumelia, in Varna. His advocacy of the aggressive expansionist policy made him the main rival of Çandarlı Halil Pasha the Younger. He died in 1453 in Bursa after he had witnessed the success of the expansionist policy he has always been advocating when Ottomans captured Constantinople and executed his main rival Çandarlı Halil Pasha.