Gruev lived to see the frightful flight of the Turkish asker (troops) from his native village-Smilevo. He was engaged, during the course of the insurrection, in numerous skirmishes with the Turkish army and gallantly defended the temporarily freed Smilevo. But with the arrival in Macedonia of over 300,000 Asatics, any progress of the insurrection was made impossible and in a period of six weeks it was completely crushed. Gruev put himself to task now to tour the various revolutionary districts, disarm the insurgents, and store up the war materials for future use. The years 1903-1904 were the most disastrous for the Macedonian people. But Gruev and his fellow-workers kept up the spirit of the peasants and continued the work of organization and preparation for another opportune time to strike once more. "For great affiars,"said Gruev, "are necessary great forces. Liberty is a great thing: it requires great sacrifices." Gruev was an untiring worker. He rebuilt the temporarily wrecked organization, made it more systematic and far more powerful. But unfortunately, on his way through the village of Rousinovo (Maleshevsko district), Gruev and his cheta (band) were betrayed to the Turks. In a violent and heroic struggle with numerous Turkish troops he fell dead, on December 23, 1906.
When the Turkish Central authorities heard that among the killed was Gruev himself, they immediately telegraphed to the local Turkish governor to uncover the burried bodies and take a photograph of Gruev. The augurs of the autocratic bureaucracy of Constantinople wanted to convince themselves of the fact that the great giaur-the disturber of the empire, Gruev-was really dead. Thus ended the epic life of the great Macedonian apostle-Damian Gruev!