The chronicles contain references to the birth of two daughters by Ivan III and Sophia Palaiologina under the name Theodosia. Two cases of coincidence of names in the same princely family in the same time period (sources also report the birth of at least two Elenas by Sophia and Ivan with the difference of ten years) caused a lot of scientific disputes about the reliability of the information, the real existence of all the mentioned princesses and the correlation of facts with the personalities of each of them [2, p. 287, n. 20; 3, p. 41-43; 4, p. 399–401, etc.]. The case of Theodosia (or Feodosya) is as follows. The Moscow chronicler mentions the three daughters of Ivan and Sophia, and only one Elena, in the future the wife of the Grand Duke of Lithuania Alexander, called by name [VII, p. 222; 4, p. 399]. The Nikon Chronicle contains information about the birth of two Elenas and two Theodosias. The first couple, Elena and Theodosia, were born in 1474 and 1475, respectively; the second pair - in 1484 and 1485 [III]. The redundancy of coinciding facts casts doubt on the reliability of the information in this source, or, at least, indicates confusion in dates and names [4, p. 400]. Roughly the same picture is observed in the Resurrection and Simeonovskaya chronicles. In other chronicles, as a rule, only one pair of princesses Elena and Theodosia, who were born either in the 1470s or in the 1480s. appears (see, for example, Typographical, Novgorod fourth, Sophia`s second and Lvov chronicles) [4, p. 400-401]. To date, historiography does not have an unambiguous answer to the question of how many daughters in the family of Ivan III were named Theodosia. However, most researchers believe that Theodosia, who eventually became the wife of Prince Vasily Danilovich of Kholmsk, was born precisely in 1475 [3; 5; 6] As for Theodosia the second, as V.A. Kuchkin conventionally calls her, she either died in infancy [3, p. 42], or did not exist at all [4, p. 401].
In 1480, Sophia took the children, including Theodosia, from Moscow to Beloozero, where in the monastery of St. Cyril of Belozero the princely family waited until the danger from Khan Akhmat had passed. A year later, Theodosia with her sisters Elena and Evdokia will return to Moscow.
Apparently, Theodosia was present at the discussion of the conditions of the marriage of Elena's elder sister with the Grand Duke of Lithuania Alexander Cazimirovich. Theodosia is also mentioned in the business correspondence, where the details of the upcoming wedding and future life in Vilnius are discussed [I; X, p. 189, 194, 207, 239, 253, 254; 3, p. 41].
According to seniority, Theodosia herself was to marry next to Elena. Prince Vasily Danilovich of Kholmsk, the governor of Ivan III, was chosen as her husband [1, p. 112-113, 287; 8]. V.D. Nazarov notes the political calculation that was present when this decision was made: Vasily Danilovich was the son of Daniil of Kholmsk, a prominent politician, and at the same time a relatively new person at court. According to the scientist, the approach of the Kholmskys was one of the steps aimed at forming a new circle of boyar aristocracy to replace the disgraced princes Patrikeevs [6, p. 75–89; 7, p. 73-81]. The wedding took place on February 13, 1500 [II, p. 1-5; VI, p. 232; VII, p. 222, VIII, p. 173; IX, p. 16-17]. The marriage, however, did not last long. The very next year, Princess Theodosia died. Her remains have not survived, but she was probably buried in the necropolis of the Ascension Cathedral in the Moscow Kremlin [9, p. 132].
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