During Mahmud's reign, the raids on the Byzantine borders continued.
[1] Ali Bey crossed the Sakarya River during his raids but later signed a treaty with the Byzantines.
With this agreement, the Turkmen gathered around Osman Bey of the nascent Ottoman Empire.
This switching of sides by the Turkomans further weakened the influence and power of Çobanli Mahmud Bey.
In 1309, Suleyman Pasha of the Beylik of Isfendiyar raided Mahmut Beg's palace and killed him.