Yakov "Golden Tooth" Maskalevsky was a Ukrainian rebel ataman and a member of the Makhnovist movement.

He was enlisted during World War I and he eventually became a full knight of St. George, receiving the rank of ensign.

[1] While Nestor Makhno briefly joined the Red Army, Maskalevsky continued to fight against the Bolsheviks, he dispersed their organizations and distributed land to the peasants.

On 22 March 1921 a Golden Tooth detachment of 150 people with 3 machine guns went to Yeysk on the ice of the Sea of Azov, and part remained in the Mariupol district and awaited the arrival of Viktor Belash.

[2] On 13 July 1921 a Golden Tooth detachment knocked the 2nd company of the 90th battalion of the Cheka out of the village of Maryevka.