Editing List of Bulgarian monarchs (section)

== Second Bulgarian Empire (1185–1422) ==
{{Main|Second Bulgarian Empire}}

=== House of Asen (1185–1256) ===
{{Main|Asen dynasty}}

{| class="wikitable" style="width:100%; text-align:center;"
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! style="background:#D4F2CE; width:18%" | Name
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! style="background:#D4F2CE; width:62%;" | Succession and notes
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|[[File:Coin of Peter II (IV).png|80px]]
|'''[[Peter II of Bulgaria|Peter II]]'''{{efn|Enumerated as '''Peter IV''' if the rebels [[Peter Delyan]] (Peter II) and [[Constantine Bodin]] (Peter III) are also counted.<ref name="Mladjov-2015" />}}<br /><small>Петър</small>
|1185–1197<br /><small>(12 years)</small>
|Aristocrat, probably of [[Vlachs|Vlach]] origin,<ref name="Fine-1991" /><ref name="Vasary-2005" /> with no relation to previous monarchs.<ref name="Vasary-2005" />{{efn|The House of Asen has in the past sometimes been suggested to have descended from the monarchs of the First Bulgarian Empire given that [[Kaloyan of Bulgaria|Kaloyan]] (1196–1207) was identified by [[Pope Innocent III]] (1198–1216) in a letter as descended from them. This is conventionally interpreted as the pope merely recognizing Kaloyan as the legitimate successor (and not a genealogical descendant) of the earlier ''tsar''s, in a way common for the time.<ref name="Vasary-2005" />}} [[Uprising of Asen and Peter|Revolted]] against the Byzantine Empire alongside his brother [[Ivan Asen I of Bulgaria|Ivan Asen]] 1185 after being slighted by Emperor [[Isaac II Angelos]]. Proclaimed himself Bulgarian emperor in November 1185. After years of fighting, Isaac in 1188 recognized the brothers as rulers of an independent Bulgarian state, though skirmishes continued thereafter. Ivan Asen was later made the senior co-ruler (ruling from [[Veliko Tarnovo|Tarnovo]]), with Peter ruling from [[Veliki Preslav|Preslav]].<ref name="Fine-1991" /> Murdered in 1197.<ref name="Various-2021">{{Cite book |last=Various |url=https://books.google.com/books?id=gN4zEAAAQBAJ |title=Routledge Library Editions: Historiography |date=2021 |publisher=Routledge |isbn=978-1-317-26808-6 |pages=111 |language=en}}</ref>
|-
|[[File:Coin of Ivan Asen I.png|80px]]
|'''[[Ivan Asen I of Bulgaria|Ivan Asen I]]'''<br /><small>Иван Асен</small>
|{{Circa}} 1188–1196<br /><small>(c. 8 years)</small>
|Brother of Peter II;<ref name="Mladjov-2015" /> co-leader in their [[Uprising of Asen and Peter|revolt]] against the Byzantine Empire. Made senior co-ruler at some point between 1187 and early 1190.<ref name="Fine-1991" /> Murdered in 1196.<ref name="Various-2021" />
|-
|[[File:Leaden seal of Kaloyan.png|80px]]
|'''[[Kaloyan of Bulgaria|Kaloyan]]''' (Ivan I)<ref name="Mladjov-2015" />{{efn|In his formal titulature, Kaloyan referred to himself by the name ''Kaloyan'' (rendered in Latin as ''Calojoannes'').<ref name="CurtaFlorin"/> He is additionally counted as "Ivan I" since Ivan (without a double name) was his original name; "Kaloyan" derives from the Greek ''Kaloïōannēs'' and is an ornate and flattering nickname meaning "John [Ivan] the Good".<ref name="Mladjov-2015" />}}<br /><small>Калоян (Иван)</small>
|1196–1207<br /><small>(9 years)</small>
|Brother of Peter II and Ivan Asen I.<ref name="Mladjov-2015" /> Foiled efforts at separatism by some of the nobility and consolidated royal power. Considerably expanded Bulgarian territory through wars with Serbia, Hungary, and the Byzantine Empire. Increased his expansion into Byzantine lands following the collapse of the Byzantine Empire due to the [[Fourth Crusade]] (1202–1204). Later fought against the [[Latin Empire]], defeating its first emperor ([[Baldwin I, Latin Emperor|Baldwin I]]). Believed to have been murdered.<ref name="Detrez-2014" />
|-
|[[File:Seal of Boril.jpg|80px]]
|'''[[Boril of Bulgaria|Boril]]'''<br /><small>Борил</small>
|1207–1218<br /><small>(11 years)</small>
|Son of a sister of Peter II, Ivan Asen I and Kaloyan.<ref name="Detrez-2014" /><ref name="Mladjov-2015" /> Boril's reign saw unsuccessful wars against Serbia, the Latin Empire, and the competing successor states of the Byzantine Empire, as well as the spread of the [[Bogomilism|Bogomilist]] sect in Bulgaria. Deposed and blinded by his cousin Ivan Asen II.<ref name="Detrez-2014" />
|-
|[[File:Coin of Ivan Asen II.png|80px]]
|'''[[Ivan Asen II]]'''<br /><small>Иван Асен</small>
|1218–1241<br /><small>(23 years)</small>
|Son of Ivan Asen I.<ref name="Mladjov-2015" /> Overthrew Boril.<ref name="Detrez-2014" /> Ivan Asen II aspired to make himself the ruler of a joint Bulgarian-Byzantine Empire<ref name="Various-2021" /> and his reign saw the Second Bulgarian Empire reach its greatest extent.<ref name="Detrez-2014" /> Defeated the [[Empire of Thessalonica]] at the [[Battle of Klokotnitsa]] (1230), whereafter much of its territory was annexed and Bulgaria became the most powerful state in southeastern Europe.<ref name="Rosser-2012" /> Re-established the independent [[Bulgarian Orthodox Church]] under a [[Patriarch of All Bulgaria|patriarch]] in 1235.<ref name="Detrez-2014" />
|-
|
|'''[[Kaliman Asen I of Bulgaria|Kaliman Asen I]]'''<br /><small>Калиман Асен</small>
|1241–1246<br /><small>(5 years)</small>
|Son of Ivan Asen II.<ref name="Mladjov-2015" /> Underage at the time of his accession. Murdered after a reign of five years.<ref name="Petkov-2008" />
|-
|[[File:Michael-Asen-Kastoria.jpg|80px]]
|'''[[Michael II Asen|Michael Asen I]]'''{{efn|Often referred to as '''Michael II Asen''', although this is incorrect. This enumeration derives from [[Boris I]] (852–889) having been baptized under the name Michael. Boris I however continued to most often merely use "Boris" and the emperors of the Second Bulgarian Empire used the double name ''Michael Asen'' (Asen being part of the name and not some other form of qualifier) rather than just "Michael".<ref name="Mladjov-2015" />}}<br /><small>Мицо Асен</small>
|1246–1256<br /><small>(10 years)</small>
|Son of Ivan Asen II.<ref name="Mladjov-2015" /> Underage at the time of his accession.<ref name="Petkov-2008" /> Ambushed and killed in 1256 by a group of Bulgarian nobles after a treaty in which Michael Asen I returned all of Bulgaria's territorial gains in former Byzantine territory to the [[Empire of Nicaea]].<ref name="Curta-2021b">{{Cite book |last=Curta |first=Florin |url=https://books.google.com/books?id=f85JEAAAQBAJ |title=The Routledge Handbook of East Central and Eastern Europe in the Middle Ages, 500-1300 |date=2021 |publisher=Routledge |isbn=978-1-000-47624-8 |language=en |chapter=New Powers–Serbia and Bulgaria}}</ref>
|-
|
|'''[[Kaliman Asen II of Bulgaria|Kaliman Asen II]]'''<br /><small>Калиман Асен</small>
|1256<br /><small>(less than a year)</small>
|Grandson of [[Ivan Asen I of Bulgaria|Ivan Asen I]].<ref name="Mladjov-2015" /> Proclaimed emperor after Michael Asen I's death.<ref name="Curta-2021b" /> Married his predecessor's widow but was ineffective at maintaining power<ref name="Mladjov-2015" /> and died within a year.<ref name="Curta-2021b" /> His death extinguished the male line of the House of Asen.<ref name="Curta-2021b" />
|}

=== Successors of the Asenids (1256–1280) ===
The end of the male line of the House of Asen plunged Bulgaria into a chaotic period of fragmentation and civil wars between numerous lines of claimants.<ref name="Curta-2021b" />

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|[[File:Coin of Mitso Asen.png|80px]]
|'''[[Mitso Asen of Bulgaria|Mitso Asen]]'''<br /><small>Мицо Асен</small>
|1256–1263<br /><small>(7 years)</small>
|Husband of [[Maria Asenina of Bulgaria|Maria Asenina]], a daughter of [[Ivan Asen II]].<ref name="Mladjov-2015" /> Proclaimed emperor in southeastern Bulgaria either in opposition to Kaliman Asen II<ref name="Petkov-2008" /> or after his death. Unclear if he ever gained control of the capital of [[Veliko Tarnovo|Tarnovo]],<ref name="Fine-1994" /> though he may have held it briefly<ref name="Curta-2021b" /> in 1256–1257.<ref name="Mladjov-2015" /> Later established himself in the lands surrounding [[Mesembria]]. Gave Mesembria to the Byzantine Empire in 1263 after attacks by [[Konstantin Tih|Constantine I Tih]], in return being allowed to live out his life in exile in [[Anatolia]].<ref name="Fine-1994" />
|-
| style="background:#E6E6E6;" |[[File:Rostislav Mikhailovich (crop).jpg|80px]]
| style="background:#E6E6E6;" |[[Rostislav Mikhailovich]]<br /><small>Ростислав Михайлович<br />(''Pretender in [[Vidin]]'')</small>
| style="background:#E6E6E6;" |1257–1262<br /><small>(5 years)</small>
| style="background:#E6E6E6;" |Father-in-law of Michael Asen I and Kaliman Asen II.<ref name="Curta-2021b" /> Invaded Bulgaria, though was unable to take the capital of [[Veliko Tarnovo|Tarnovo]]. Occupied [[Vidin]] and governed the surrounding area as self-proclaimed Bulgarian emperor, supported by the [[Kingdom of Hungary]].<ref name="Curta-2021b" /> Left landless after an attack by [[Konstantin Tih|Constantine I Tih]] in 1260, though restored with Hungarian aid in 1261, claiming the same title again until his death in 1262.<ref name="Fine-1994" />
|-
|[[File:KonstantinTih.jpg|80px]]
|[[Konstantin Tih|'''Constantine I''' Tih]]{{efn|The actual regnal name of this monarch was '''Constantine Asen''', as attested in contemporary Bulgarian documents. The conventional designation "Konstantin Tih" (meaning "Constantine, the son of Tih[omir]") was never used in medieval Bulgaria itself and instead derives from Byzantine sources.<ref name="Mladjov-2015" />}}<br /><small>Константин Асен</small>
|1257–1277<br /><small>(20 years)</small>
|Elected emperor in [[Veliko Tarnovo|Tarnovo]] in 1257 by the Bulgarian nobility, in opposition to both Mitso Asen and Rostislav. Married [[Irene Doukaina Laskarina]], a granddaughter of [[Ivan Asen II]], in order to boost his legitimacy.<ref name="Curta-2021b" /> Ultimately victorious in the civil wars of the 1250s and 1260s.<ref name="Curta-2021b" /> Later remarried to [[Maria Palaiologina Kantakouzene]], a niece of the Byzantine emperor [[Michael VIII Palaiologos]].<ref name="Mladjov-2015" /> Defeated and killed in battle by the peasant rebel [[Ivaylo of Bulgaria|Ivaylo]].<ref name="Mladjov-2015" /><ref name="Vasary-2005">{{Cite book |last=Vásáry |first=István |url=https://books.google.com/books?id=7DJWyg97IggC |title=Cumans and Tatars: Oriental Military in the Pre-Ottoman Balkans, 1185–1365 |date=2005 |publisher=Cambridge University Press |isbn=978-1-139-44408-8 |pages=36, 80–82, 89, 95–96 |language=en}}</ref>
|-
| style="background:#E6E6E6;" |[[File:Coin of Jacob Svetoslav.png|80px]]
| style="background:#E6E6E6;" |[[Jacob Svetoslav]]<br /><small>Яков Светослав<br />(''Pretender in [[Vidin]]'')</small>
| style="background:#E6E6E6;" |1266–{{Circa}} 1273<br /><small>(c. 7 years)</small>
| style="background:#E6E6E6;" |Noble of princely Russian origin.<ref name="Fine-1994" /> Initially loyal to Constantine I Tih, fighting on his side with the title of ''[[Despot (court title)|despot]]'' in the wars against Hungary (1261) and the Byzantine Empire (1262–1263). Came in possession of [[Vidin]] {{Circa}} 1263 and gradually fell under Hungarian suzerainty. Referred to as "Bulgarian emperor" in Hungarian documents from 1266 onwards. Asserted his independence from Hungary {{Circa}} 1273 and re-aligned himself with Constantine again; adopted as a second son by Constantine's wife (making him second-in-line to the throne) but later poisoned by her {{Circa}} 1275.<ref name="Fine-1994" />
|-
|
|'''[[Michael Tih|Michael Asen II]]'''<br /><small>Михаил Асен</small>
|1277–1279<br /><small>(2 years)</small>
|Son of Constantine I; previously junior co-emperor {{Circa}} 1272–1277.<ref name="Mladjov-2015" /> Underage at the time of his accession, his mother [[Maria Palaiologina Kantakouzene]] ruled as regent.<ref name="Mladjov-2015" /> In 1278 made co-ruler with [[Ivaylo of Bulgaria|Ivaylo]], who married Maria.<ref name="Mladjov-2015" /> Deposed by the Byzantine-supported [[Ivan Asen III of Bulgaria|Ivan Asen III]] and sent as a captive to Constantinople.<ref name="Vasary-2005" />
|-
|
|"'''[[Ivaylo of Bulgaria|Ivaylo]]'''"{{efn|It is doubtful that Ivaylo was this ruler's real name given that the only medieval source using it (the [[Svrljig gospels]]) might instead be informally referring to his successor Ivan Asen III. The only other names applied to him in medieval sources are the Greek nicknames ''Lakhanas'' and ''Kordokoubas'', attested in Byzantine sources.<ref name="Mladjov-2015" />}}<br /><small>Ивайло</small>
|1278–1279<br /><small>(1 year)</small>
|An illiterate swineherd<ref name="Vasary-2005" /> who became leader of a peasant uprising and seized control of much of Bulgaria. Became a legitimate monarch through marriage with [[Maria Palaiologina Kantakouzene]], Michael Asen II's mother,<ref name="Mladjov-2015" /><ref name="Vasary-2005" /> who married him on the condition that Michael Asen II's rights continued to be respected.<ref name="Vasary-2005" /> Escaped to the [[Golden Horde]] in exile after [[Ivan Asen III of Bulgaria|Ivan Asen III]] took control of Bulgaria. Killed by [[Nogai Khan]] after requests from the Byzantines.<ref>{{Cite book |last1=Maiorov |first1=Alexander V. |url=https://books.google.com/books?id=pmBCEAAAQBAJ |title=The Routledge Handbook of the Mongols and Central-Eastern Europe |last2=Hautala |first2=Roman |date=2021 |publisher=Routledge |isbn=978-1-000-41745-6 |pages=203 |language=en}}</ref>
|-
|
|'''[[Ivan Asen III of Bulgaria|Ivan Asen III]]'''<br /><small>Иван Асен</small>
|1279–1280<br /><small>(1 year)</small>
|Son of [[Mitso Asen of Bulgaria|Mitso Asen]].<ref name="Mladjov-2015" /> Supported as puppet emperor of Bulgaria by the Byzantine emperor [[Michael VIII Palaiologos]], against Ivaylo and Michael Asen II. Took control of Bulgaria with the help of the Byzantine army.<ref name="Vasary-2005" /> Fled to the Byzantine Empire after a brief reign due to fearing the ambitions of the aristocrat [[George I of Bulgaria|George Terter]], whereafter the Bulgarians proclaimed George Terter emperor in his stead.<ref name="Mladjov-2015" />
|}

=== House of Terter (1280–1292, first time) ===
{{Main|Terter dynasty}}
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|[[File:Coin of George Terter I.png|80px]]
|'''[[George I of Bulgaria|George Terter I]]'''<br /><small>Георги Тертер</small>
|1280–1292<br /><small>(12 years)</small>
|Leading member of the Bulgarian aristocracy. Wishing to safeguard the position of Ivan Asen III, the Byzantine emperor [[Michael VIII Palaiologos]] arranged for George Terter to divorce his wife and marry [[Kira Maria Asenina of Bulgaria|Kira Maria Asenina]] (Ivan Asen III's sister). Despite this, George Terter plotted against Ivan Asen III, who eventually fled to the Byzantines. The Bulgarians thereafter proclaimed George Terter emperor.<ref name="Mladjov-2015" /> Overthrown by [[Nogai Khan]] of the [[Golden Horde]] and fled to Byzantium.<ref name="Hupchick-2002">{{Cite book |last=Hupchick |first=D. |url=https://books.google.com/books?id=sQGIDAAAQBAJ |title=The Balkans: From Constantinople to Communism |date=2002 |publisher=Springer |isbn=978-0-312-29913-2 |pages=84–85 |language=en}}</ref><ref name="Vasary-2005"/>
|}

=== House of Smilets (1292–1299) ===
{{Main|Smilets dynasty}}
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|
|'''[[Smilets of Bulgaria|Smilets]]'''<br /><small>Смилец</small>
|1292–1298<br /><small>(6 years)</small>
|Member of a prominent Bulgarian noble family<ref name="Vasary-2005" /> though without known connections to previous Bulgarian royalty.<ref name="Mladjov-2015" /> Husband of [[Smiltsena Palaiologina]], a niece of the Byzantine emperor [[Michael VIII Palaiologos]].<ref name="Mladjov-2015" /> Made emperor of Bulgaria (as a puppet ruler) by [[Nogai Khan]] of the [[Golden Horde]].<ref name="Hupchick-2002" /><ref name="Vasary-2005" />
|-
|
|'''[[Ivan II of Bulgaria|Ivan II]]'''{{efn|Sometimes referred to as '''Ivan IV Smilets''', numbered after Ivan Asen I–III (then considered Ivan I–III) and not counting [[Kaloyan of Bulgaria|Kaloyan]] as Ivan I nor counting [[Ivan Vladislav of Bulgaria|Ivan Vladislav]]. The rulers named Ivan Asen however used that name as a double name and are more appropriately numbered as such; Ivan Vladislav also used a double name. The combination ''Ivan Smilets'' for this ruler is modern and does not occur in any contemporary sources.<ref name="Mladjov-2015" />}}<br /><small>Иван</small>
|1298–1299<br /><small>(1 year)</small>
|Son of Smilets.<ref name="Mladjov-2015" /> Underage at the time of his accession, Ivan II briefly succeeded his father before being deposed after [[Chaka of Bulgaria|Chaka]]'s invasion of Bulgaria.<ref name="Hupchick-2002" /> Later lived out his life in exile in the Byzantine Empire.<ref name="Georgieva-2017">{{Cite journal |last=Georgieva |first=Sashka |date=2017 |title=Bulgarian-Serbian Marital Diplomacy from the End of 13th to the Beginning of 14th Century |url=https://www.ceeol.com/search/article-detail?id=642630 |journal=Историјски часопис |language=English |issue=66 |pages=85–127 |doi=10.34298/IC1766085G |issn=0350-0802|doi-access=free }}</ref> Due to the small number of sources (two documents) some historians have disputed whether Ivan II actually reigned.<ref name="Georgieva-2017" />
|}

=== House of Borjigin (1299–1300) ===
{{Main|Borjigin}}
{| class="wikitable" style="width:100%; text-align:center;"
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|[[File:Coin of Chaka.png|80px]]
|'''[[Chaka of Bulgaria|Chaka]]'''<br /><small>Чака</small>
|1299–1300<br /><small>(1 year)</small>
|Son-in-law of [[George Terter I]] and son of [[Nogai Khan]] of the [[Golden Horde]]. Invaded Bulgaria, assisted by [[Theodore Svetoslav of Bulgaria|Theodore Svetoslav]] (a son of George Terter I). Proclaimed himself as emperor of Bulgaria and achieved some recognition with Svetoslav's help. Came into conflict with the Golden Horde khan [[Toqta]] and then overthrown and strangled by Svetoslav.<ref name="Hupchick-2002" /><ref name="Vasary-2005" /> Some historians have argued that Chaka was never emperor of Bulgaria, but merely dominated it through his brother-in-law Theodore Svetoslav.<ref name="Pavlov-1999">{{Cite journal |last=Pavlov |first=Plamen |date=1999 |title=Bil li e tatarinăt Čaka bǎlgarki car? |url=https://www.ceeol.com/search/article-detail?id=204992=Историческо бъдеще |language=Bulgarian |issue=1–2 |pages=71–75 |doi=10.34298/IC1766085G |issn=0350-0802|doi-access=free }}</ref>
|}

=== House of Terter (1300–1323, second time) ===
{{Main|Terter dynasty}}
{| class="wikitable" style="width:100%; text-align:center;"
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|[[File:Silver coin of Theodore Svetoslav.png|80px]]
|'''[[Theodore Svetoslav of Bulgaria|Theodore Svetoslav]]'''<br /><small>Тодор Светослав</small>
|1300–1322<br /><small>(22 years)</small>
|Son of George Terter I; previously junior co-emperor {{Circa}} 1285–1292.<ref name="Mladjov-2015" /> Overthrew and strangled Chaka, with support from [[Toqta]] of the [[Golden Horde]].<ref name="Hupchick-2002" /><ref name="Vasary-2005" /> Ended the period of Mongol dominion over Bulgaria<ref name="Rosser-2012" /> and waged wars against both the Byzantine Empire and various autonomous Bulgarian nobles.<ref name="Logio-1974">{{Cite book |last=Logio |first=George Clenton |url=https://books.google.com/books?id=A29pAAAAMAAJ |title=Bulgaria, Past & Present |date=1974 |publisher=AMS Press |isbn=978-0-404-56133-8 |pages=307 |language=en}}</ref> Mostly successful;<ref name="Logio-1974" /> succeeding in reconsolidating the empire.<ref name="Rosser-2012" />
|-
|[[File:Coin of George Terter II.png|80px]]
|'''[[George II of Bulgaria|George Terter II]]'''<br /><small>Георги Тертер</small>
|1322–1323<br /><small>(1 year)</small>
|Son of Theodore Svetoslav; previously junior co-emperor {{Circa}} 1321–1322.<ref name="Mladjov-2015" /> Intervened in the [[Byzantine civil war of 1321–1328]]<ref name="TSvetkov-1993">{{Cite book |last=T︠S︡vetkov |first=Plamen |url=https://books.google.com/books?id=VR5pAAAAMAAJ |title=A History of the Balkans: A Regional Overview from a Bulgarian Perspective |date=1993 |publisher=EM Text |isbn=978-0-7734-1956-8 |pages=112, 205, 315 |language=en}}</ref> and spent much of his brief reign warring with the Byzantines, for instance recapturing [[Plovdiv]].<ref name="Fine-1994" /> His death marked the extinction of the direct Terter line.<ref name="Fine-1994" />
|}

=== House of Shishman (1323–1331) ===
{{Main|House of Shishman}}
{| class="wikitable" style="width:100%; text-align:center;"
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|[[File:Coin of Michael Shishman.png|80px]]
|'''[[Michael Shishman of Bulgaria|Michael Asen III]]'''{{efn|Many sources erroneously refer to this emperor as '''Michael III Shishman'''. His regnal name, attested in both Bulgarian and Byzantine sources, was the double name ''Michael Asen''. The designation "Michael Shishman" (which connects him to his father [[Shishman of Vidin]]) is not attested in contemporary sources.<ref name="Mladjov-2015" />}}<br /><small>Михаил Асен</small>
|1323–1330<br /><small>(7 years)</small>
|Matrilineal great-grandson of [[Ivan Asen II]].<ref name="Mladjov-2015">{{Cite journal |last=Mladjov |first=Ian |date=2015 |title=Monarchs' Names and Numbering in the Second Bulgarian State |url=http://cejsh.icm.edu.pl/cejsh/element/bwmeta1.element.ojs-doi-10_18778_2084-140X_05_09 |journal=Studia Ceranea |volume=5 |pages=267–310 |doi=10.18778/2084-140X.05.09 |hdl-access=free |hdl=11089/18406}}</ref> Previously semi-independent despot of [[Vidin]]. Elected as emperor by the Bulgarian nobility after George Terter II's death due to being considered the strongest local candidate. Retook some territory that had been lost to the Byzantines during the brief [[interregnum]] before his election.<ref name="Fine-1994" />
|-
|[[File:King John Stephen of Bulgaria 19th Century.JPG|80px]]
|'''[[Ivan Stephen of Bulgaria|Ivan Stephen]]'''<br /><small>Иван Стефан</small>
|1330–1331<br /><small>(1 year)</small>
|Son of Michael Asen III; previously junior co-emperor {{Circa}} 1323–1324.<ref name="Mladjov-2015" /> Deposed after a brief reign in favour of his cousin [[Ivan Alexander of Bulgaria|Ivan Alexander]] in a ''[[coup d'état]]'' headed by elements of the Bulgarian nobility. After his deposition, Ivan Stephen fled to Serbia and then to the Byzantine Empire.<ref name="Fine-1994" />
|}

=== House of Sratsimir (1331–1422) ===
{{Main|Sratsimir dynasty}}The rulers of the House of Sratsimir, patrilineal descendants of the despot [[Sratsimir]], are in lists of monarchs often designated as part of the Shishmanid dynasty, with which they only share matrilineal descent. Through their matrilineal descent from the House of Shishman, the rulers of the House of Sratsimir were also descendants of the House of Asen.<ref name="Mladjov-2015" />
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|[[File:Ivan Alexander.jpg|80px]]
|'''[[Ivan Alexander of Bulgaria|Ivan Alexander]]'''<br /><small>Иван Александър</small>
|1331–1371<br /><small>(40 years)</small>
|Son of [[Keratsa Petritsa]], a sister of [[Michael Shishman of Bulgaria|Michael Asen III]].<ref name="Mladjov-2015" /> Proclaimed emperor following a ''[[coup d'état]]'' headed by elements of the Bulgarian nobility.<ref name="Fine-1994">{{Cite book |last1=Fine |first1=John V. A. |url=https://books.google.com/books?id=LvVbRrH1QBgC |title=The Late Medieval Balkans: A Critical Survey from the Late Twelfth Century to the Ottoman Conquest |last2=Fine |first2=John Van Antwerp |date=1994 |publisher=University of Michigan Press |isbn=978-0-472-08260-5 |pages=172–183, 269, 273–274, 366, 368, 422 |language=en}}</ref> Allied with [[Stefan Dušan]] of the [[Serbian Empire]], who was eclipsing Bulgaria's power. Managed to capture some territories from the Byzantine Empire.<ref name="Fine-1994" /> Divided the empire among his sons to avoid succession problems, leading to Bulgaria's fragmentation. Allied with the [[Ottoman Turks]] against the Byzantines, inadvertently accelerating the [[Ottoman conquest of the Balkans]].<ref name="Detrez-2014" />
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| style="background:LightCyan;" |[[File:Ivan Alexander with Michael Asen IV (coin).jpg|80px]]
| style="background:LightCyan;" |'''[[Michael Asen IV of Bulgaria|Michael Asen IV]]<ref name="Mladjov-2015" />'''<br /><small>Михаил Асен<br />(''Junior co-ruler'')</small>
| style="background:LightCyan;" |<small>Never ruled [[Suo jure|in his own right]]</small>
| style="background:LightCyan;" |Eldest<ref name="Andreev-1993">{{cite book |last=Andreev |first=Jordan |title=Bǎlgarija prez vtorata četvǎrt na XIV v. |publisher=Sv. Kliment Ohridski |year=1993 |location=[[Veliko Tarnovo|Veliko Tǎrnovo]] |pages=23–52, 67–75 |language=Bulgarian |id=[[OCLC]] [http://worldcat.org/oclc/69163573 69163573]}}</ref> son of Ivan Alexander; junior co-emperor {{Circa}} 1332–1355.<ref name="Mladjov-2015" /> Led an army in the defense against an Ottoman invasion in 1354–1355, during which he was killed in battle near [[Sofia]].<ref name="Andreev-1993" />
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| style="background:LightCyan;" |[[File:Ivan Asen IV.png|80px]]
| style="background:LightCyan;" |'''[[Ivan Asen IV of Bulgaria|Ivan Asen IV]]<ref name="Mladjov-2015" />'''<br /><small>Иван Асен<br />(''Junior co-ruler'')</small>
| style="background:LightCyan;" |<small>Never ruled [[Suo jure|in his own right]]</small>
| style="background:LightCyan;" |Son of Ivan Alexander; junior co-emperor {{Circa}} 1337–1349.<ref name="Mladjov-2015" /> Led an army in the defense against an Ottoman invasion in 1349, during which he was killed in battle near [[Sofia]].<ref name="Andreev-1993" />
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|[[File:Ivan Sratsimir portrait 1.JPG|80px]]
|'''[[Ivan Sratsimir of Bulgaria|Ivan Sratsimir]]'''<br /><small>Иван Срацимир<br />(''Ruling in [[Tsardom of Vidin|Vidin]]'')</small>
|1356–{{Circa}} 1397<br /><small>(c. 41 years)</small>
|Son of Ivan Alexander; previously junior co-emperor {{Circa}} 1337–1356.<ref name="Mladjov-2015" /> Granted [[Vidin]] and the surrounding lands by his father as autonomous emperor while his younger brother [[Ivan Shishman of Bulgaria|Ivan Shishman]] inherited [[Veliko Tarnovo|Tarnovo]].<ref name="Detrez-2014" /> Immediately tried to take control of all of Bulgaria after his father's death, though was defeated by Ivan Shishman.<ref name="Fine-1994" /> The [[Tsardom of Vidin|Vidin empire]] was largely conquered by the [[Ottoman Empire]] in 1396/1397 and Ivan Sratsimir was deposed and taken prisoner.<ref name="Detrez-2014" /><ref name="Pavlov-2009" />
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|[[File:53 IoSisiman.JPG|80px]]
|[[Ivan Shishman of Bulgaria|'''Ivan Shishman''']]<br /><small>Иван Шишман<br />(''Ruling in [[Veliko Tarnovo|Tarnovo]]'')</small>
|1371–1395<br /><small>(24 years)</small>
|Son of Ivan Alexander; previously junior co-emperor {{Circa}} 1356–1371.<ref name="Mladjov-2015" /> Made the heir to [[Veliko Tarnovo|Tarnovo]] over the elder Ivan Sratsimir due to the influence of his mother [[Sarah-Theodora]]. Fought off Ivan Sratsimir's attempt at capturing Tarnovo.<ref name="Fine-1994" /> Made a vassal of the Ottoman Empire. Tried to gain Hungarian aid to reassert his independence, which led to the Ottomans invading his lands. Tarnovo and most of Bulgaria was captured in 1393,<ref name="Fine-1994" /> followed by [[Nikopol, Bulgaria|Nikopol]] and Ivan Shishman's other remaining territory in 1395. Allegedly murdered by the Ottomans after the capture of Nikopol.<ref>{{cite book |last1=Андреев |first1=Йордан (Jordan Andreev) |title=Българските ханове и царе |last2=Лалков |first2=Милчо (Milcho Lalkov) |publisher=Абагар (Abagar) |year=1996 |isbn=954-427-216-X |location=Велико Търново ([[Veliko Tarnovo]]) |pages=286 |language=bg |trans-title=The Bulgarian Khans and Tsars}}</ref>
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| style="background:LightCyan;" |[[File:Ivan Asen V.jpg|80px]]
| style="background:LightCyan;" |'''[[Ivan Asen V of Bulgaria|Ivan Asen V]]<ref name="Mladjov-2015" />'''<br /><small>Иван Асен<br />(''Junior co-ruler'')</small>
| style="background:LightCyan;" |<small>Never ruled [[Suo jure|in his own right]]</small>
| style="background:LightCyan;" |Son of Ivan Alexander; junior co-emperor 1356–{{Circa}} 1388.<ref name="Mladjov-2015" /> Recorded to have presided over [[Council of Tarnovo (1360)|church synods at Tarnovo]] (1360) together with his father and [[Ivan Shishman of Bulgaria|Ivan Shishman]].<ref>{{cite book |last=Златарски |first=Васил (Vasil Zlatarski) |title=България през XIV-XV век (Bulgaria during the 14th and 15th Centuries) |publisher=Изток–Запад (Anubis) |year=2005 |isbn=954-321-172-8 |pages=144–148 |language=bg |author-link=Vasil Zlatarski}}</ref>
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| colspan="4" style="background: #93C572; text-align: center;" | ''Bulgaria was conquered by the [[Ottoman Empire]] in the [[Bulgarian–Ottoman wars]] (1345–1396), resulting in the fall of the [[Second Bulgarian Empire]]''
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|[[File:Constantine of Vidin.jpg|80px]]
|[[Constantine II of Bulgaria|'''Constantine II''']]<br /><small>Константин{{efn|All known contemporary documents refer to Constantine II merely by the name ''Constantine''. It is possible that he (like [[Konstantin Tih|Constantine I]]) used the double name ''Constantine Asen'', especially given that ''Asen'' was incorporated into the double names of three of his uncles. None of the surviving documents are from Constantine's chancery and no known seals or charters exist, making it impossible to confirm this hypothesis.<ref name="Mladjov-2015" />}}<br />(''Ruling in [[Tsardom of Vidin|Vidin]]'')</small>
|{{Circa}} 1397–1422<br /><small>(c. 25 years)</small>
|Son of Ivan Sratsimir; previously junior co-emperor {{Circa}} 1395–1397.<ref name="Mladjov-2015" /> Remained in control of at least some parts of his father's domains around Vidin,<ref name="Mladjov-2015" /> probably initially as an Ottoman vassal,<ref name="Pavlov-2009" /> for most of the time until his death in 1422.<ref name="Mladjov-2015" />
|}