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Chalkokondyles was born to an old (11^th c.) and politically influential Athenian family, but following the end of French rule in Florence, his father opposed the ruling Acciaiolis and was banished from Athens in 1435. The family moved to Mystras in the Peloponnese where Demetrius received his early education under Georgius Gemistus (Plethon) (ca. 1355-1454) among others. At some point he returned to Athens to complete his education. There were scholars in his family, notably his cousin, Laonicus Chalkokondyles (ca. 1430-ca. 1470), historian of the last century-and-a-half of the Byzantine Empire. Demetrius’s scholarly endeavors led him to Plato, but he was sufficiently adept at Latin to help Marsilio Ficino (1433-99) with his Latin translation of Plato.  In 1449, age 26, he moved to Rome for the opportunity to study with the Greek Aristotelian Theodore Gaza (1398-1475). 

Italian proficiency in Greek during the Renaissance was largely due to the efforts of native-born Greeks who brought the language to the courts and classrooms of the fifteenth century. Chalkokondyles and his colleagues the Platonist Ficino (1433-99), the editor Poliziano (Agnoto Ambrogini) (1454-94), and Cristoforo Landino (1424-98) were instrumental in the effort. 

He taught first at Perugia, where he taught the Latin poet Giovanni Maria Campano (1429-77). About 1455 he returned to Rome and joined the circle of Greek exiles centered on Cardinal Bessarion (1403-73), who was attempting to reconcile the rift in the Eastern church between the Aristotelians and the Platonists with the help of John Argyropoulos (1415-87) and Ficino. In 1462 the Italian proverb-writer and Platonist Michael Apostolius (1420-78) wrote Bessarion accusing the Platonist Gaza of being too Aristotelian.  Chalkokondyles, ever loyal to his teacher, defended Gaza with a pamphlet denouncing the attack. 

Arriving at Padua in 1463, he became the first Professor of Greek at any European university to receive a fixed payment. He continued to write pamphlets and give speeches supportive of the liberation of Greece from Ottoman rule. In 1466 he edited a manuscript (Laur. 31.28) of the Planudian Anthology (now part of the Greek Anthology), but he longed for a better position. Bessarion was unable to secure him one and Chalkokondyles dismissed Gaza’s offer of a private position in Rome in 1472. 

He removed to Florence, where he joined the circle of humanists supported by Lorenzo de Medici (1449-92) and gave lectures and tutored at the Studium in Florence for twenty years.  The names of his most prominent students include the author of a number of editiones principes Janus Lascaris (ca. 1445-1535), translator and Pope Leo X (Giovanni di Lorenzo de’ Medici) (1475-1521), author of The Courtier, Baldassare Castiglione at Milan (1478-1529), the scholar and poet Giglio Gregorio Giraldi (1479-1552), Stefano Negri (1475-1540), in Florence, the German classicist Johannes Reuchlin (1455-1522). Though he was widely respected as a teacher and lecturer on Platonic philosophy, by the age of fifty he had yet to produce any substantial body of work that promoted the Byzantine Greek philosophical and cultural presence in Italy.

Bessarion died in 1472 and Gaza three years later, the year in which Chalkokondyles succeeded John Argiropoulos (1415-87) as professor of Greek. Chalkokondyles was now a senior member of the circle portrayed on the fresco of the choir of Santa Maria Navella del Ghirlandaio with his colleague Cristoforo Landio (1424-98) and the rising Poliziano (Agnolo Ambrogini) (1454-94), who worked on the Medicis’ favorites, Homer and Catullus. Even as Poliziano gave his famous introductory lecture on Homer to reassert his authority, Chalkokondyles asserted his authority by producing in 1488 the editio princeps of Homer, dedicated to Lorenzo, the first work of great literature printed in Florence entirely in Greek. He included ancient testimonia, theBatrachomymachia and the Homeric Hymns. The influence of Eustathius is seen throughout and he relied heavily on Florentine manuscripts.   

In 1479 Lorenzo called him to the Florentine Studium, where his circle included Poliziano, Pico della Mirandola (1463-94), and Giovanni de Medici (1475-1521). Four years earlier, at the age of 61, he married and fathered 10 sons, the last, Ptolemy, was born when his father was 78. 

C. found his role diminished. Poliziano was now a leader of Greek studies and with Athens captured by the Turks, declared that Florence was the new Hellas. Chalkokondyles wished to move to Rome to tutor Cardinal Giovanni di Medici, meeting with Pope Innocent VIII in that same year 1488, through the offices of his old student G. Lorenzi, the librarian of the Vatican. 

Following the death of Lorenzo in 1492, he moved to the Greek chair at Milan at the invitation of the Duke of Milan, Ludovico Sforza (1452-1508). Freed from the friction with Poliziano, he felt a greater sense of freedom had fewer professional disagreements, and enjoyed teaching a younger generation of students, including Baldassare Castiglione (1478-1529), Gian Giorgio Trissino (1478-1550), Giovanni Maria Cattaneo (d. 1529/30), Paolo Giovio (1483-1552), Giglio Gregorio Girardi (1479-1552), and perhaps most important of all, the German Catholic humanist Johann Reuchlin (1455-1522). Indicative of his devotion to teaching is the publication in 1494 of a school grammar of Greek. In the following year, feeling the need for a Greek grammar more accessible than the grammar of Theodorus, he published his Erotemata, a summary in question-and-answer form. In that same year he produced another editio princeps, of Isocrates, followed by another editio princeps, of the Suda.  

Thinking his career in danger when the French occupied the Duchy of Milan in 1499 and ousted Lodovico Sforza, C. fled to Ferrara, but in 1501 Louis XII’s legate Georges d’Amboise, invited Chalkokondyles back to Milan. There he completed his last work, a translation into Latin of the 11^th century compendium of Cassius Dio by Giovanni Xifilinius Dio. Erasmus called him “probus” and “eruditus” while Poliziano called him “aridus et ieiunus” (arid and meagre). Wrote Sandys, “He gave proof of much insight (not unmixt with caprice) in the emendation of Greek texts. In integrity of character and in gentleness of disposition he stands higher than the ordinary Greeks of his time.”