[19][20][21][22][23][24] In 1461–1462, Demetrios reproduced a manuscript of Plato's Timaeus while in Corfu and in 1465, he copied Plotinus's Enneads while in Crete;[19][25][26][27][28][29] after his completion of Plato's work, Demetrius wrote the following note: "Η βίβλος ἥδε ἐγράφη δι᾿οἰκείας χειρὸς ἐμοῦ Δημητρίου Τριβώλη Πελοποννησίου ἐκ Σπάρτης τὰς διατριβὰς ποιοῦντος ἐν Κερκυραίων νήσῳ · μετὰ τὴν τῆς ἡμετέρας πατρίδος ἅλωσιν" which translates as: "The present book was written by my own hand of Demetrios Trivolis Peloponnesian from Sparta who made these works in the island of the Kerkyreans after the fall of our fatherland" (referencing the fall of his native Laconia to the Ottomans).

[21] In another note, Demetrios writes: "κάλλιστον βιβλίον εμόν εστι κτήμα Δημητρίου Τριβώλη Πελοποννησίου εκ Σπαρτης.

[36][37] He knew prominent figures of the Renaissance era such as the Venetian printer Aldus Manutius and made the acquaintance of scholars Angelo Poliziano, Marsilio Ficino, Pico della Mirandola, Scipio Callerges, and Fonteguerri.

[41] In 1515, Grand Prince Vasili III asked the abbot of the monastery to send him a certain monk by the name of Savva to translate a number of religious texts.

After Vasili III rejected his request to go home, Maximus continued to work on translations and correcting the books for divine service.

Observing the "defects" and injustices of Muscovite life, which seemed to him in direct opposition to his Christian ideals, Maximus began to expose them and criticize the authorities, attracting different people with similar views, such as Ivan Bersen-Beklemishev, Vassian Patrikeyev, and others.

Maximus's relations with Vassian Patrikeyev, Ivan Bersen-Beklemishev, and Turkish ambassador Skinder, Metropolitan Daniel's hostility towards him, and Greek's own negative attitude towards Vasili III's intention to divorce Solomonia Saburova decided his fate.

Maximus's "irritating" behavior at the monastery, newly discovered mistakes in his translations, and old suspicions of his unscrupulous relations with the now dead Turkish ambassador were all used against him once again at a new sobor in 1531.

Worn out by the harsh conditions of his imprisonment, Maximus acknowledged some minor mistakes in his translations and excessive wine drinking.

He interpreted and explained for his Muscovite readers a large number of points of ancient and Biblical history, Orthodox Church practice and teachings, and features of the contemporary world outside of Muscovy.