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The future Metropolitan of Kiev was a typical representative of the intellectual environment of late Byzantine society, practicing various forms of intellectual communication, common in his time. Thus, Isidore corresponded with different persons: he wrote to his fellow students in Constantinople as well as to the Byzantine emperors Manuel II and his son John VIII Palaeologus. The analysis of these writings and also the character of Isidore's education, lead to the conclusion that Isidore was not just an ordinary Byzantine intellectual, but a humanist with a specific attitude to science, philosophy and religion, who belonged to elite groups, the so-called "theaters" or "salons", in which the intellectuals used to discuss a wide range of scientific issues.

The turning point in the life of a future Kiev Metropolitan was the appointment of Isidore to the post of Kathegoumenos of the Emperor's Monastery of St. Demetrius in Constantinople and his further participation as an ambassador in the work of Basel Council, which was devoted to the discussion of a project of Ecumenical Council intended to overcome the schism between the Western and Eastern Churches. Having analyzed Isidore's speech at the Basel Council, the author concludes that it was here that Isidore first claimed the idea of Union which determined his future and turned to be in some sense his lifeline: shortly after Isidore returned from Basel, he was elected the Metropolitan of Kiev so that he could ensure the representation of the Russian Church at the Union Council and later implement the Union.

The "Russian" period of Isidore's life is also reflected in historical sources. The analysis of these sometimes very laconic references, as well as a set of documents on the history of the Ferrara-Florentine Council of 1438–1439 indicates that Isidore was almost silent, with the exception of a few insignificant remarks. However, approximately from the spring of 1439 and till the Union was signed, Isidore together with another Metropolitan, Bessarion of Nicaea, undertook a series of practical actions aimed at inducing the Orthodox clergy to join the Union, thanks to which the unification was achieved, albeit at the expense of the purity of the Orthodox faith. In this case, Isidore consistently pursued the policy of unification in accordance with a key strategy of Byzantine Emperor John VIII Palaeologus, which, apparently, was in harmony with his own convictions. Motives of the Kiev Metropolitan's actions should be sought, first of all, in a pragmatic political consideration and intention to achieve unity between the Churches with the main purpose — to save Byzantium, dying in the struggle against the Turks, with military support from the West. In this regard Isidore behaved as a typical Hellenic patriot who was ready to do anything to save his homeland.

In the areas of his legacy, as well as on the territory of the Byzantine Empire in the 1440's, Isidore promoted the Florentine Union, using his own method of persuasion, in accordance with which he attracted the Orthodox Christians appealing exclusively to the Byzantine patristic heritage. In the territories controlled by Isidore as the Metropolitan of Kiev, the news of the unification of the Churches was perceived with suspicion and skepticism, and somewhere it was encountering great resistance. A severe conflict caused by the announced unification broke out in Moscow between Grand Prince Vasily Vasilyevich and Metropolitan Cardinal Isidore, with the result that the latter was imprisoned and deposed by the Russian bishops' council. It was for the first time that Russian people faced such situation that is why, probably, they let Isidore to escape. Isidore's character and his activity in Russia were remembered by Russian people for a long time, and as soon as his name was mentioned in some work, it was accompanied from now by an unflattering characteristic reflecting rather negative attitude towards Isidore. The Church of Constantinople represented in Russia by Isidore was also compromised, which undoubtedly played a role in establishing autocephaly of the Russian Church in 1448 under St. Iona (Jonas) of Moscow.

Study of the last period of Isidore's life is associated with a number of problems, the unambiguous resolution of which sometimes has seemed unattainable. First of all, they are: lack of published sources on the Roman Curia life in the 1440–60's, and in general insufficient historiography information concerning the convocation of the Council of Mantua and the Greeks in Italy after the fall of Constantinople. Having studied the available sources, the author concludes that the last period of Isidore's life was devoted to propaganda of the Union in the territory of Byzantine Empire; Isidore carried out a full-fledged activity as Cardinal of the Roman Church first in the rank of Cardinal-Presbyter, and from 1451 — Cardinal-Bishop. Roman popes sent various blessings to Isidore, giving him temples, monasteries and whole dioceses "in feeding". At the end of his life, in 1459, "the Ruthenian Cardinal" got a title of the Latin Patriarch (the titular Patriarch) of Constantinople, already conquered by the Turks, against which Isidore fought desperately in 1453, taking most active part in defending the city from the onslaught of Turkish troops. During the seizure of Constantinople, Cardinal Isidore nearly died, was sold into slavery, he stayed unrecognized because of the wound on his head which prevented him from being executed by Sultan, so Isidore happily escaped. When the capital of the Roma state fell, the question of Union lost its original relevance, but until the end of his days Cardinal Isidore did not give up hope for a revival of the Empire and was desperately doing his utmost. In the 1450–60's Isidore tried to organize, together with Bessarion of Nicaea, Pope Nicholas V, Callixtus III and Pius II a new Crusade against the Turks; he also took part in the Council of Mantua, though all these efforts never produced any significant result. The last days of his life Cardinal Isidore spent in Rome, and there he was buried: first in the Church of the Holy Apostles, and later — in the Cathedral Basilica of St. Peter.

Some attention of historiography has been given to the issue of the library and literary heritage of Isidore of Kiev, however the available studies are devoted either to his writings in general and become already outdated, or to his individual treatises, which makes it impossible to get a complete and distinct idea of Isidore as a prominent bibliophile and literary figure of the late Byzantine period. For his long life Isidore had managed to collect or work with an impressive number of books. Isidore made some notes in most of these manuscripts, part of the manuscripts was copied by his own hand, and some manuscripts were taken from the Papal library in the last decade of Isidore's life. At the moment, scientists have more than 160 codes that Cardinal was dealing with; the number of the books read by Isidore puts him on a par with such outstanding minds of the past as St. Photius of Constantinople and Michael Psellos.

Analysis of the Isidore's library allows to reveal the scope of his interests more or less clearly and to understand the features of a late-Byzantine intellectual in general. The range of his reading was extremely broad and included books of philosophical, historical, rhetorical, astrological and astronomical, natural-science and theological subjects. In fact there were only few manuscripts of theological content that passed through Isidore's hands or were kept in his personal library. This was probably due to the fact that basically Isidore collected books of the humanities and natural sciences, and he could refer to theological and patristic books any time in monastery or other institutional libraries. Anyway, a number of patristic books in Greek, taken by Isidore in the Papal library in 1455, can confirm his interest in the theological subject. Probably, there could have been much more books of that kind, but the Papal library was just started, so the number of books in Greek could be very limited.

Metropolitan Cardinal Isidore left behind a significant literary heritage, which, although inferior in terms of the amount of works to his younger contemporaries, such as St. Mark of Ephesus, Patriarch of Constantinople Gennadios II Scholarios or Bessarion of Nicaea, nevertheless, occupies a prominent place in the late Byzantine literature of the first half of the 15th century. The author has identified 52 works covering various literary genres: panegyrics in honor of Byzantine and German emperors; letters in Greek as well as letters translated into Latin, Italian and Slavic; theological, hymnographic and historical canonical works. All works are attributed to Isidore thanks to the surviving autographs, although no work has an inscription of his full name, with the exception of messages from Buda and to the Kholmsk elders.

The epistolary heritage and panegyrics of Isidore present great importance for historical science. Isidore's letters in Greek testify to him being a talented scientist and inscribe his personality in the environment of the late Byzantine intellectual elite, while the Latin letters become the most valuable source on the history of siege and fall of Constantinople and the subsequent reaction of the world community to this tragic event. Panegyrics in honor of the royal persons give a huge volume of historically important information necessary to provide a historical overview of the system of government, foreign and domestic policies of the Byzantine and German emperors in the late 14th — first third of the 15th centuries.

Isidore's theological works are of less importance for the Orthodox theology. Although they bear a vivid imprint of originality and intellectualism of the originator, they are just rehashing of patristic thoughts and quotations already known for a long time. These works have significance only for the idea of Union developed by Latinophile theologians within the framework of the discourse connected with the Basel and Ferrara-Florentine Councils and the subsequent reaction of the Orthodox population of the Byzantine Empire to this idea of Union. Based on the analysis of these works, the author shares the hypothesis of Ioannis Polemis that Isidore considered it possible to enter into union irrespectively of any theological basis.

The hymnographic works of Isidore are of particular interest: 4 prayers and 2 unpublished acoluthies were written in honor of the Archangel Michael and St. Martyr Demetrius of Thessalonica. If the prayers reflected a kind of political ideology of the Byzantine Empire and were written for specific people and due to certain circumstances, the two liturgical orders were composed by Isidore, apparently, in the throes of religious feeling. Isidore carried his monastic ministry in the imperial monasteries in honor of the Archangel Michael near Monemvasia and St. Martyr Demetrius in Constantinople; and, probably, for some reason he was not satisfied with the hymnography in honor of these saints available in liturgical books.