Proposed as daughter of Ioannes Doukas, ruler of Thessaly & his wife .... Palaiologos
(JUAN=Ioannes) of Serbian-Hungarian line was in the in the Greek time-area, fought far and wide by the sultan & his father, from whose harem the two sisters were recovered.

Angelina of Greece (c. 1380 - Segovia, c. 1440) was a woman of Balkan origin who later established herself in Segovia.

Some researchers consider her a princess belonging to the House of Angevin, who, together with her sister Maria, were taken captive by Sultan Bayezid’s troops after the Battle of Nicopolis. Next, after the Turkish defeat at the Battle of Ankara, they became a part of Timur’s harem, who then offered them to King Henry III’s ambassadors as his gift for the Castilian king.

Angelina was one of the most beautiful women the ambassadors and the court of Henry III saw, and a famous Spanish love poem was created to honour her. ... After some time Angelina married a wealthy knight, Diego Gonzalez de Contreras, who was a councilman in Segovia. Angelina and Diego had many children, and their grandson, Rodrigo de Contreras (1502-1558), became a governor of Guatemala. In 1437 at the age of 70 Diego Gonzalez died, while his wife outlived him and lived in Segovia for some time.

From her marriage to Diego González de Contreras several children were born, including:

• Isabel González de Contreras who married Ruy Vázquez de Tordesillas.[6]
• Fernán González de Contreras. (Speculative)
• John of Segovia, theologian. (Speculative) /!\(1395-1458)--> therefore wrongly since Angelina was sent to Spain just only in 1403 /!\

Her descendants include her biographer, Juan de Contreras y López de Ayala, Marquis of Lozoya, academic and historian.[5]

• https://en.wikipedia.org/wiki/Angelina_de_Grecia

The traditional historiography goes, in accordance with the inscription on her tomb, that Angelina was the daughter of a Count 'Juan' (i.e. Ioannes, John, Ivan, István, etc.), and the illegitimate granddaughter of a certain king of Hungary, probably Andrew, Duke of Calabria, the titular king of Hungary. [1]

Later, it was speculated that he was an illegitimate descendant of Louis I of Hungary by way of an illegitimate son, which would be Count Juan. [1]

At present it has been proposed that she was a girl of Greco-Serbian origin, a daughter of John Uroš, count of Thessaly and titular Emperor of the Serbs, Greeks, and Bulgarians. This affiliation would likely be the one that explains her being known in Spain under the surname de Grecia (of or from Greece). In the case of the name Angelina, by which she was known in Spain, a Byzantine affiliation has been noted. [2]

1. ^ The sepulchral inscription was: AQUI YACE DOÑA ANGELINA DE GRECIA, HIJA DEL CONDE JUAN, NIETA DEL REY DE UNGRÍA, MUGER DE DIEGO GONZÁLEZ DE CONTRERAS, REGIDOR DESTA CIUDAD
2. ^ At present, his house houses the National Distance Education University in Segovia.

   ---

Prima del 1402, entrò a far parte, insieme alla sorella Maria, dell'harem del sultano ottomano Bayezid I.

• Le ipotesi più probabili suggeriscono che due potrebbero essere state catturate o nel 1387, quando Murad I, padre di Bayezid, prese Tessalonica, e in seguito da lui cedute al figlio,
• o essere state catturate direttamente da Bayezid durante l'assedio del 1391.

Nel 1402, Angelina e Maria, in qualità di consorti del sultano, insieme a una donna spagnola, Catalina, erano fra le donne presenti nel campo ottomano di Ankara quando Bayezid I fu sconfitto e catturato da Tamerlano, che prese in custodia le donne dell'harem del prigioniero. Più tardi, le tre furono consegnate a Payo Gonzales de Sotomayor e Hernán Sánchez de Palazuelos, ambasciatori del re Enrico III di Castiglia[1].

https://it.wikipedia.org/wiki/Angelina_di_Grecia#cite_ref-:0_1-1

the fact that they were in the harem in 1402 is not a hypothesis, the hypotheses are just only about how and when they ended up there.

Note: It is not likely Angelina and Maria were concubines; they were Christian captives of war, and concubines were required to convert.

The origins of Angelina and Mary

From Burkiewicz, Lukasz. (2016). Two Christian princesses offered as Timur's present for King Henry III of Castile. The analysis of the introduction to Ruy Gonzalez de Clavijo's narrative (1403-1406), „Perspektywy Kultury” 2015, vol. 13 (2), pp. 159-178.. Perspektywy Kultury. 13. 159-178. < link > Page 169-170

Who were Doña Angelina de Grecia and Mary and where did they come from? Their origins are unknown. According to the inscription in Segovia, Angelina was a daughter of a Hungarian priest Juan, that is John (Ivan), and a granddaughter of the King of Hungary (Louis I of Hungary or Sigismund of Luxemburg) 46.

The inscription is confirmed by other source materials. G.Argote de Molina, the author of the first edition of Clavijo’s narrative (Seville 1582), claimed that Angelina and Mary, who came from a Hungarian princely family and were related to the King of Hungary, were taken captive by Timur together with the whole Bayezid’s harem after the Battle of Ankara 47.

Angelina was supposed to have been born in Hungary, although it is not known where exactly. It must have been around 1381, since she was 15 when she was taken captive by the Ottomans 48 . Juan de Contreras wrote that, when the Hungarian King Sigismund of Luxemburg accompanied by Western-European knights left Buda and headed south towards the border with the Ottoman Turks, he was accompanied by a large court, including two princesses, Angelina and Mary, the daughters of John (Ivan), the Duke of Slavonia in Croatia, who was the cousin of the Hungarian ruler 49 . On 12th September 1396 the crusaders reached Nicopolis and began the siege. The Christian forces lost the battle, which took place on the 25th September 50 Angelina and Mary, who stayed in the camp, not manage to escape on time and were taken captive by Sultan Bayezid’s Turkish troops 5 1.

If Angelina was born around 1381, her parents most probably had not been born after 1360, which offers us several clues regarding her family 52. If we assume that her father was a member of the Angevin dynasty,
we should start with the analysis of this dynasty, making reference to the latest findings (2015) of an expert at Hungarian Middle Ages, Stanisław A. Sroka 53.

At the beginning, let us have a closer look at hypotheses referring to Angelina and Mary’s potential father and grandfather, which are put for ward in the Spanish literature:

1. R.T. Kahane and M.R.Lida de Malkiel claim that Louis I of Hungary from the Angevin dynasty was the father of Duke John (Ivan). Louis was born in 1326 and ruled as a king in the period 1342-1382 54. Historioraphy confirms that he had three daughters with his second wife, Elizabeth of Bosnia: the first one– Catherine– died in childhood 55 ; the second one– Mary– became Queen of Hungary and married King Sigismund of Luxemburg (they did not have any children) 56; while the third one – Hedwig– became Queen of Poland and the wife of Władysław Jagiełło, with whom she had a daughter, Elizabeth Bonifacia, who died soon after birth. Louis did not have a son, and nothing is known of his illegitimate offspring 57.

2. J. de Contreras assumes that John, Duke of Slavonia and Angelina’s father, was the child of Andrew, Duke of Calabria (born in 1327), who belonged to the Capetian House of Angevin. Andrew was the son of Hungarian King Charles I and Elizabeth of Poland; he later became the Duke of Calabria and husband of Queen of Naples, Joanna I, and was murdered in September 1345 58 . However, historiography mentions only one child of Joanna and Andrew, Charles Martel, who died at the age of 3 in 1348. Moreover, J. de Contreras, quoting Juan Alonso Calderón’s work I have not heard about (Calderon was the councelor of King Philip IV (1621-1665)), also questions the argument that Angelina could have been Andrew’s granddaughter. His claims are refuted by the fact that there is no living offspring of Andrew 59.

S.A. Sroka does did not mention any potential illegitimate children of Louis and Andrew, which could be a starting point in our quest for the origins of Angelina’s father. Moreover, he describes Louis as a relatively well-behaved ruler in the context of his era 60 . Thus, in the face of the lack of confirmation in source materials, the claim that Duke John was a son of Louis or Andrew cannot be justified.

Another clue might be offered by a look at the Angevin rulers in Slavonia, Dalmatia, and Croatia. In this regions rulers were awarded the title of Duke and Ban of a particular sub-region 61:

1. Historiography mentions the Duke of Slavonia, Dalmatia, and Croatia named John, who, according to the Privilege of Buda of 1355, was a successor to the Polish throne. He was the youngest son of Duke Stephen
of Slavonia from the Capetian House of Angevin (who was King Louis I’ brother) and Margaret of Bohemia (who was the daughter of Charles IV, Holy Roman Emperor). John was born in 1354 but died in 1360, so he could not have been Angelina and Mary’s father 62.

2. Charles III of Naples was the Ban (but not the Duke) of Slavonia, Dalmatia, and Croatia. Also known as the King of Hungary Charles II, he was the son of Louis of Durazzo, Count of Gravina, and Margaret of Sanseverino. His exact date of birth is not known, and it is assumed that he was born between 1345 and 1357. In 1365 King Louis I of Hungary awarded him the title of the Ban of Slavonia, Dalmatia, and Croatia. With his wife Margaret of Durazzo, he had the following children: Mary, who died after birth, Joanna, who became a ruler of Naples Joanna II, and Ladislaus (born in 1376), who was also the king of Naples (1382-1386) and the king of Hungary (1385-1386). We know nothing about his other children 63.

3. Is it thus possible that Angelina’s father could be someone connected with the banate of Slavonia, Dalmatia, and Croatia but not related (or closely related) to the Angevin dynasty? In Hungarian historiography two bans called John (Ivan) are mentioned: John of Palisna and John Horvat. John of Palisna was the Ban of Slavonia in the period between 1385 and 1386 and in 1389 (he died in 1391) and a member of the Order of Saint John. John Horvat (the Ban in the years 1392-1394, he died in 1394) 64 , was the head of the powerful Horvat family and the leader of the opposition against Sigismund of Luxemburg 6 5. He was involved in kidnapping Elizabeth of Bosnia and her daughter Mary, for which he was later executed by order of King Sigismund of Luxemburg 66. Unfortunately, this path does not offer us any clues as to Angelina and Mary’s origin, either. ...

... The fact that J. de Contreras’s work contains several contradictions adds to the difficulty in tracing Angelina and Mary’s roots. These contra-dictions result from the fact that he was not familiar with the archival materials from Seville discovered by M.Gaibrois de Ballesteros, which provided the exact date of the arrival of the princesses to Castile 72 . First of all, Contreras claimed that Angelina reached Castile in 1398 (1399), when she was 18, which he emphasised 73 . It cannot be true, as she could not have done it earlier than in 1402 (in 1940s Gaibrois de Ballesteros corrected this date to 1403), after the Bayezid’s defeat and the return of Castilian ambassadors from Timur. J. de Contreras also wrote that Angelina and her husband moved to the parish of San Juan de los Caballeros in 1399, but again this date is much earlier than historical facts would allow 74 . What is more, J. de Contreras made a mistake when giving the date of the Battle of Nico-polis– both with regard to the day (29th September) and the year (1395) 75 .

Conclusion

The diplomatic mission of Pelayo Gomez de Sotomayor and Fernando de Palazuelos was a success. It was followed by another mission sent by Henry III to Timur, which was led by Ruy Gonzalez de Clavijo, who was accompanied by Alfon Peaz de Santa-Maria and Gomez de Salazar. They left Castile on 21st May 1403 setting off from Cádiz in Andalusia 76 . In November 1404 the embassy began the return journey, however, without obtaining the answer to the Castilian King’s letter 77 . Timur, who was then very ill, was not interested in a campaign against the Ottomans, and turned his attention to China. Clavijo came back to Castile on 24th March 1406 78. In subsequent years he served at Henry III’s court as a chamberlain, and he held this office till the King’s death in 1407. Next he came back to Madrit, where he died on 2nd April 1412.

Summing up our considerations devoted to two mysterious Christian princesses offered as Timur’s gift for King Henry III, it can be concluded that:

1. The likelihood that Angelina and Mary belonged to the Hungarian royal family is not very high. The analysis of the Angevin family tree and academic sources on the Crusade of Nicopolis do not mention Duke John (Ivan), the son of the Hungarian king and the father of two daughters, who were kept as captives by the Turks or captured by the Ottomans after the Battle of Nicopolis.

2. Maybe the princesses were members of a noble Hungarian family, and, as such, following the Castilian tradition, were referred to as princesses. Unfortunately, we have no sources regarding Hungarian nobility who were captured by the Ottomans after the Battle of Nicopolis.

3. It is also probable that Angelina and Mary, who belonged to one of noble Hungarian families, were captured by the Ottoman Turks during one of their raids on the border areas, but tradition changed it into the Battle of Nicopolis. This version is quite probable, although, of course, not certain, given the lack of evidence for either option.

4. The French chronicle Chronique du religieux de Saint‑Denys, contenant le règne de Charles VI de 1380 à 1422, written by an anonymous monk from the Basilica of Saint Denis in Saint Denis (now a suburb of Paris), reports that King Sigismund of Luxemburg allowed the crusaders to take with them a large number of women, which was supposed to contribute to slackening of morals in Christian troops 79. This might also serve as a clue in our considerations.

5. The hypothesis of Angelina and Mary’s Greek roots cannot be rejected, not only because of the middle name Griega, which might indicate a Greek mother (according the the Catalan tradition), but because it is possible that the girls were members of the Angelos family.

6. Also, the words of the poet, Francis Imperial, that Angelina could be Tuerta, that is Tarta, coming from the country of Tatars, should be taken into consideration. Maybe she came from Asia, and her facial features, resembling European ones, allowed her contemporaries to assume she came from Hungary or Greece. In the face of scientific evidence on the girls’ origins available to us, this hypothesis seems probable.

The above considerations do not provide the answer to the question of the origins of Angelina and Mary, two women who were Timur’s gift for King Henry III of Castile, yet they indicate a direction of further research. The answer may be found in the analysis of the Hungarian and Byzantine nobility.

References

1. https://en.wikipedia.org/wiki/Battle_of_Nicopolis The Battle of Nicopolis took place on 25 September 1396 and resulted in the rout of an allied Crusader army (assisted by the Venetian navy) at the hands of an Ottoman force, raising the siege of the Danubian fortress of Nicopolis and leading to the end of the Second Bulgarian Empire. It is often referred to as the Crusade of Nicopolis as it was one of the last big Crusades of the Middle Ages, together with the Crusade of Varna in 1443–1444. By their victory at Nicopolis, the Turks discouraged the formation of European coalitions against them. They maintained their pressure on Constantinople, tightened their control over the Balkans, and became a greater threat to Central Europe.[15]
2. Kahane, Renée Toole, and María Rosa Lida de Malkiel. “Doña Angelina de Grecia.” Nueva Revista de Filología Hispánica 14, no. 1/2 (1960): 89–97. http://www.jstor.org/stable/40297484.
3. https://en.wikipedia.org/wiki/Bayezid_I Consorts: … Angelina Hatun (1380 - 1440). Daughter of the Hungarian count János (Juan), was freed by Timur and handed over to Henry III of Castile. She later married Diego González de Contreras. Maria Hatun. Angelina's sister, she was freed by Timur and handed over to Henry III of Castile. She later married Payo González de Soto Mayor.
4. https://walintonia.wordpress.com/2012/10/27/angelina-de-grecia/ Angelina was known as one of the most beautiful women of her time and married Diego Gonzalez de Contreras, of former Castilian nobility. They had numerous offspring, including a great-grandson Rodrigo de Contreras, governor of the newly conquered Guatemala. A daughter of Rodrigo, Jerónima de Contreras, married in the midst of feasts and rejoicing in 1564 with Polo de Ondegardo, the great chronicler.
5. https://archive.aramcoworld.com/issue/200603/the.diplomacy.of.the.s... 1402 Timur captures Ottoman Ankara and sends embassy with freed Christian women to Henry III of Castile.
6. Burkiewicz, Lukasz. (2016). Ł. Burkiewicz, Two Christian princesses offered as Timur's present for King Henry III of Castile. The analysis of the introduction to Ruy Gonzalez de Clavijo's narrative (1403-1406), „Perspektywy Kultury” 2015, vol. 13 (2), pp. 159-178.. Perspektywy Kultury. 13. 159-178. < researchgate.net > The aim of this article is to consider of the origins of Angelina and Mary, two women who were Timur's gift for King Henry III of Castile (1390-1406). In 1402 these two Christian princesses had been offered to a diplomatic mission preceding Clavio's embassy. One of the princesses, Angelina, is often referred to in the Spanish literature and historiography. Some researchers consider that Angelina and Maria were taken captive by Turkish after the Battle of Nicopolis. Next, after the Turkish defeat at the Battle of Ankara, they became a part of Timur's harem, who then offered them to King Henry III's ambassadors as his gift for the Castilian king. The main source for this study is an addition to the edition of narrative of Ruy Gonzalez de Clavijo, the ambassador of King Henry III, who was sent on a diplomatic mission to Timur, resided in Samarkand. Angelina became a symbol of the era known for fierce warfare between the growing Ottoman Empire, the Byzantine Empire and the Kingdom of Hungary, with a subsequent defeat of crusaders at the Battle of Nicopolis (1396) and the fate of Christian war captives. Although we do not know much about their origin, the women are of continuous interests to researchers, and their fate has entered the Castilian tradition.
7. "The life of Maria Gomez de Sotomayor: The Ottoman slave who had suffered great dispair in both Ottoman lands and outdoor lands." < tumblr >
8. Hernán Sánchez de Palazuelos was an ambassador in the service of Henry III, the King of Castille. He is best known as part of the diplomatic mission to the Turco-Mongol conqueror Tamerlane. Hernán Sánchez de Palazuelos traveled with another ambassador, Payo Gómez de Sotomayor, to meet Sultan Bayazid I following the defeat of the Christians at the Battle of Nicopolis (1396). However, when the two Castilians reached the lands of Bayazid, the sultan was at war with the lord of the Mongols, and after his defeat at the Battle of Ankara (1402) they met the Mongol Emperor Timur (Tamerlane). He is said to have treated them with respect and sent them back accompanied with his own ambassador: Mohamad Alcagi (El-Kesh). He also gave them three slaves, Greco-Hungarian princesses, captured at the Battle of Nicopolis six years earlier, and who had been part of Bayezid's harem ever since. The ambassadors arrived in March 1403 in Segovia, where Angelina of Grecia, one of the freed slaves, said to be the granddaughter of the King of Hungary, married Diego González de Contreras, the mayor of the city. The ambassadors are said to have married the other two slaves, with Palazuelos marrying Catalina.
9. https://en.wikipedia.org/wiki/Ottoman_Imperial_Harem For the perpetuation and service of the Ottoman dynasty, slave girls were either captured in war, given as gifts to the Sultan and the dynastic family on special occasions, recruited within the empire, or procured from neighbouring countries to become imperial court ladies (cariyes). The number of female slaves within the harem varied over time, and the harem itself was regularly renewed as a result of the practice of manumission. Manumission of the previous sultan's concubines was especially common upon the enthronement of a new sultan. Most enslaved girls were Christian and came from various countries, regions, and ethnic groups, including Circassia, Georgia, Russia, and Africa.[22] There was no standard practice that determined what age girls entered the harem. Some arrived as children, while others entered at a later age. The Circassian slave trade was formally banned in 1854 but the ban was on paper only.[23] After 1854, almost all court lady-slaves were of Circassian origin. Circassians had been expelled from Russian lands in the 1860s and impoverished refugee parents sold their daughters in a trade that was formally banned but continued in practice.[23] Upon arrival at the palace, women and girls began a rigorous transformation process. They were converted to Islam, learned religious precepts through recitation of core Islamic creeds, and were given new Muslim names that matched their physical appearance or personality. They were trained in court manners and activities and taught the Turkish language. As part of this total transition to a new life, the women were prohibited from contacting their families. ...
10. Ruy Gonzalez de Clavijo, "Embassy to Tamerlane, 1403-1406." < GoogleBooks > Clavijo was so keen and intelligent an observer and so lively a retailer of travel gossip that this is a very welcome addition to the series. Page 178. < GoogleBooks >
11. The History of Timur ... < GoogleBooks >
12. Breue Apologia, y depos < GoogleBooks >
13. Noticias genealogicas ... < GoogleBooks >
14. The Conversos and Moriscos ... < GoogleBooks > Juan de Segovia, on the other hand, presumably came from a Converso family. Signs of this are found in his false genealogy (a strategy employed by many Conversons to disguise their Jewish roots), in which he claimed to be the son of the Hungarian Princess Angelina of Greece and the Segovian Juan de Contreras, when in reality there is no record of when or where he was born, or whether he belonged to a religious ordr or he was a secular cleric. 22