The next bey was Mahmut. During the early years of Mahmut's reign, the beylik was between two great powers: namely the Ottoman Empire to the southwest and Kadı Buhanettin to the south. Although Mahmut accepted Burhanettin's suzerainty he secretly encouraged Bayezit I of the Ottomans against Burhanettin. But the blow came from his brother Alparslan. Alparsalan revolted and captured most of his territory. Nevertheless, after Alparslan's and Burhanettin's death in 1398, he accepted the suzerainty of the Ottoman.[2]
After Timur
In 1402 Turkic warlord Timur invaded Anatolia and defeated Bayezit in the battle of Ankara. During the chaos following the battle (Ottoman Interregnum), Mahmut Bey continued as an ally of the Ottomans. However, during the revolt of Küçük Mustafa (the brother of Murat II), he supported Küçük Mustafa and killed Mihaloğlu Mehmet a descendant of Köse Mihal and a partisan of Murat II in 1423. But after the battle, he was killed by his soldiers. He had two sons; Hüsamettin Hasan and Hüsamettin Mehmet Yavuz. Although the brothers tried to continue in Samsun and Çarşamba, their beylik soon ceased to exist in about 1428.[2]