Norman Sicily, Henry VI and Andronikos Komnenos

Reading about medieval Sicily I came upon the 1185 expedition in the Byzantine Empire on behalf of a pretender (Alexios Komnenos Pinkernes) that was apparently very strong and managed to conquer and sack Thessalonike before getting defeated in November at Demetritzes by a renewed Roman army lead by the capable Alexios Branas. The Sicilian army was mostly destroyed and the invasion (and ineffectual response to it) was a leading cause in Andronikos downfall.

It came to me that there are a few possible PODs related to this:

a) The Norman army is better coordinated and organized and manages to defeat Branas. I doubt they wold be strong enough to force the Theodosian walls and they need to wait for spring to get complete naval support for a siege. Could they extract some significant concessions from Alexios Angelos?

b)Andronikos' men manage to capture/kill Alexios and so the now quite deranged Basilisk remains on the throne. No effective defense is mounted and the Normans camp outside Constantinople: what happens? Could Branas seize the moment to dispose of Andronikos, defeat the Normans and get crowned? He seemed quite capable.
Or...
b2) The City might even welcome the pretender/imposter Alexios: everything should appear better than a more and more paranoid and ineffectual Andronikos. I didn't read about any attempt of the Normans to impose the Latin rite during their campaign, so maybe, even if they are hated Latins this might not disqualify the Pinkernes?

c) The Norman invasion is avoided outright: Constance dies of some illness (malaria, drinking contaminated water, whatever) while en route to Milan to marry Henry VI Hohenstaufen or shortly after the marriage. With no formal alliance with the empire William doesn't feel secure enough to mount an expedition against Rhomania, maybe there could be some raiding or he could try seizing the Ionian islands and supporting the independence bid of Cyprus as iotl, but no 200 ship and 80000 men (I know it is a gross exaggeration, but still it had to be a very powerful army, at least ten thousand strong and with many knights) expedition to take Costantinople.

Results: Sicily doesn't waste a chunk of her military, Thessalonike is not devastated and maybe Andronikos keeps the throne longer (but there is a Bulgarian revolt incoming). Finally, HRE has no direct inheritance claim on Sicily, who will Henry marry? Effects on the HRE? Is a "national" evolution like rhe ine France was starting to undergo be possible with a reduced Italian focus (but less resources too and a possibility that the Stauden line could be extinguished much earlier).


So, lotd of questions, if someone wants to give their two cents they are warmly welcome! Especially if they are Byzantine experts.
 
The Hohenstaufen annexation of Italy was a diplomatic madterstroke. Not only was the kingdom one of the wealthiest bits of Christian real estate, but it also in a single stroke turned what had been a Papal client into an Imperial one. Had the Staufers been more lucky (Henry or Philip not dying inopportunely...) they might well have succeeded in subduing the papacy. Given that the HRE was largely defined as a secular Papacy and was locked in an ideological contest with the Pope over the two swords doctrine and the precise relationship between the two this is not the fools errand it's made out to be.
 
The Hohenstaufen annexation of Italy was a diplomatic madterstroke. Not only was the kingdom one of the wealthiest bits of Christian real estate, but it also in a single stroke turned what had been a Papal client into an Imperial one. Had the Staufers been more lucky (Henry or Philip not dying inopportunely...) they might well have succeeded in subduing the papacy. Given that the HRE was largely defined as a secular Papacy and was locked in an ideological contest with the Pope over the two swords doctrine and the precise relationship between the two this is not the fools errand it's made out to be.

Possible, although I am quite skeptical about the possibility of a political victory against the papacy, given their enormous soft power.
How could Henry and/or Philip manage to control both their German lands and Sicily? They are really different and far and way; with rich powerful and well fortified northern Italian cities in the middle.

On the other hand you are right that, for ideological reasons, the Holy Roman Emperor could not turn into a German king at this point in time.
 
Henry not dying and leaving a three year old son behind would help a lot. Papal oppsotion was important but not insurmountable; the German Princes viewed it as an insult to refuse to acknowledge their voted king as Roman Emperor and King of Italy as had been designed facto taken for granted, and indeed as the Habsburgs gained in the 15th century.

In the long run, yes, controlling Germany, Burgundy, Italy and Sicily is a formidable challenge. But it's not impossible IMHO provided one breaks away from an anachronistic national state and views it more as an Austrian style primus inter pares, even if likely to end in a Charles V style partition with a younger branch getting Sicily. Think of how long England controlled Aquitaine, for instance. Given the Staufers are based out of Swabia and their longstanding southern ambitions it's likely that they would be heavily interested in Burgundy (Provence might well get annexed/integrated by marriage in place of the French connection of OTL) as well as Tyrol and OTL Switzerland which they own. OTL two families (the Zahringen and one other) died out in the 1220s, a strong Emperor could seize that land and Austria if/when the Babenbergs die out, even if the latter will probsbly be (partially) gifted to a Habsburg or some other Swabia retainer, a stronger more stable Emperor could use the opportunity to divide the lands.

The arrival of the Mongols will probably lead to a dramatic weakening of Poland and Hungary as per OTL if not a potential threat to eg Bohemia if they settle in Hungary and start raiding like the Magyar, in any case the "core" of the realm- the Rhineland, Italy, Southwest Germany, and Provence- is a wealthy and relatively contiguous territory. The biggest threats being Papal and civic oppsotion- princely autonomy is probably cceptable to the emperors and princes. Essentially the Hohenstaufen plausibly could have become a 13th Century Habsburg dynasty, albeit one centered southward and westward.

In regards to the Eastern Empire I'm not as certain as to the ramifications, however if Constantinople is as weak as OTL a Sicilian-German invasion/intervention is not impossible, certainly interventions in e.g. Cyprus and Crete are plausible. Moreover the Empire faces several crucial challenges and a notable lack of leadership, indeed a tendency for self destructive factionalism and infighting. That said the post Komnenos Empire was evolving towards a more "dynastic" situation which although suffering from the same "problems" ie nepotism, erosion of central authority, etc also gave a degree of stsbility/continuity and a stronger more robust defensive system, as the local aristocrats could (like Frankish nobility) react to incursions more dynamically.

Bulgaria is in revolt, Anatolia crumbling, but the situation whIle difficult is not untenable. The Mongols invasions offer an excellent opportunity, in conjunction with potential crusades to Jerusalem- as her major rivals, Bulgaria, the Turks, were hit hard by the Mongols, and the post mongol fragmentation of Rum offers an excellent opportunity for a stabilized Empite to expand into Anatolia. Securing the western flank will be crucial- the Hohenstaufen annexation probably represents an excellent opportunity, it gets rid of the expansionist Normans and ensures the current rulers of Sicily will be heavily preoccupied with Italy Germany etc. And unlikely to turn their gaze east. Isolating/dealing with Bulgaria is the next immediate foreign policy priority. The Bulgarians are recently independent, recon quest would greatly shore up the prestige of the dynasty at home and abroad and push the frontier away from Greece. If bits of Anatolia are lost in the meantime it is not fatal, as Alexios proved, holding defensively there would be preferable for the moment.

All of this said the biggest issue facing Constantinople is as (nearly) always from within. The 4th Crusaders were themselves brought to Constantinople on the promises of an imperial pretender after all...
 
a) They can probably extract quite a few concessions from Isaac Angelos; and even more from a pretender of their own, should they successfully install him...what would they ask for, though? It's widely assumed that the ultimate goal of the invasion was to take the Byzantine crown for William II himself.
(I certainly hope it was - I I've been working on and off on a TL which centers on the foundation of a Hauteville Empire in Constantinople. It uses a different PoD, but no doubt some of these PoDs could also lead to the same result.)


b) Alexios Branas seems to have been personally loyal to Andronikos. In this scenario, I think either Andronikos snaps out of it or he is overthrown by his son Manuel and carted off to a monastery. In either case, Branas may still play a key role in the governance and defence of the capital.

It's hard to say what defeated the Normans in OTL: was the leadership of Branas really the key? Or was it the fact that the 5-6 different armies sent against the Normans were finally unified under one command? The question may be important for the outcome of this scenario, as well.


The Sicilians were, IIRC, not invading in the name of a single specific pretender; rather, they had two pretenders - Alexios the Cupbearer (= "Pinkernes") and a false Alexios II. And they operated in a sort of legal twilight, never specifying which of the two they actually fought to restore. So the death of the Cupbearer, in itself, doesn't really hurt the Sicilians in any way. In fact, you could argue that the fake Alexios II would be a more useful candidate for the Normans, in terms of sowing dissent and attracting support in Constantinople...but that's debatable.
 
@The Undead Martyr while I mostly agree with your post, the premises of this thread is actually the Hohenstaufen never inheriting Sicily.
I take it that it would likely mean an even bigger Papal victory in the XIII century?
Much depends on whether Henry marries again and manages to have an heir... There might even be a chance of a Welf Emperor getting elected, although I wouldn't bet on it.
 
I'm always skeptic on the chances to forge a solid HRE from Germany to Sicily and from Burgundy to Austria and Bohemia and I'm also convinced that it would be in the interest of the kingdom of Sicily not to get involved in the imperial struggle. Which means that I'd be most interested in the last alternative (Costanza dies before marrying Henry VI), since it would be quite hard to prevent a more or less faithful replay of OTL if the Houenstaufen/Hauteville marriage still happens.
The line of succession is not assured though: Tancredi would certainly become king (although in a TL where the Houenstaufen don't have any claim on the kingdom of Sicily it is quite likely that the pope will extract some concessions), assuming that ITTL too William the Good dies on schedule in 1189 (he died very suddenly when he was just 36 years old, apparently of some illness, but I was unable to find an actual cause of death).
Let's say that Tancredi dies in 1194, on schedule too (he was 55 years old, but again there is no mention of the actual cause of death). The problem is that IOTL his son and heir Roger pre-deceased him in 1193, when he was just 19 years old (maybe there was something wrong in the Hauteville line), and his other son William was 9 years old in 1194: we can assume that a regency under his mother Sibilla would be established as per OTL, and that there would be no imperial invasion (no claim ITTL). It would be quite a long regency, though, and I'm pretty sure there would be problems in the continental part of the kingdom (Tancredi died after successfully putting down a rebellion there, and a regency would probably be not strong enough to assure peace). There might be problems in Rome too, the more so if Henry VI dies also on schedule after marrying someone other than Costanza and siring a heir, but leave this aside for the moment: Sicily's influence in Rome would be anyway decreased by the unsettled status in southern Italy.
IOTL Roger III may have died in Germany in 1198, after having been deported there by Henry VI (and according to some sources he was also blinded and castrated). It would be quite possible that ITTL Roger III does not die, but rather reaches his adult age, is crowned king, marries someone (who?) and produces a bunch of sons and daughters, so ensuring the succession line. Given the early death of his brother, it is also possible that he never manages to marry and produce a heir: who would have the best claim to the throne? Note that the pope is the overlord of Sicily, and he would have to approve the crowning of a pretender from a collateral line.
 
Flagging @Basileus444 and @Vasilas as active Byzantinophiles who could be interested to this: if there is no Norman invasion and no sack of Thessalonike how stronger would Rhomania be? Conversely, could amnest victorious Norman amnrmy, camped in front of Constantinople, extract significant territorial concessions?


@LordKalvan I concur with most of your analysis, except for the fact that I think that at least some of these deaths can be easily butterflied away:

- Henry VI died of malaria near Messina, not many chances of it happening if he stays away from Sicily.

- Roger III died very young and suddenly, which points at some infectious disease that probably won't hit him at the same time or in the same way with a POD some years before. Interestingly, he had just married a Byzantine princess.

-William III was a very undesirable claimant, deported in Germany in likely terrible conditions even if he had not been mutilated. If he is king of Sicily chances are that his life expectancy would be much higher. His father also had many children, I don't think there is reason to suppose he would be sterile as William II likely was.

- Tancred himself seems to me to have died while on campaign and had been quite active until shortly before his death, which again point at infectiois disease. Maybe his death could be postponed for a couple of years.

-William II was possibly not an healthy person: it is strange that he had his barons pledge themselves to Constance (and Henry) as heirs while he and his wife (who later had several children of her own) were still relatively young. Him surviving a little longer would mean a participation in the third crusade (and likely death there).


The easiest dynastic solution would be giving a son to William II, thus avoiding the complications of having the "bastard" Tancredi getting the throne and facing revolts which are really likely to receive imperial support (I am sure that Henry would try some way to mess with Sicily even without a direct claim, given the history of hostility between Staufers and Hautevilles), but I am convinced that William was physically unable to procreate, so that would need am secondary POD.

About the vassalatic link to Rome, while it gives great leverage to the Pope (especially in a situation where someone like Tancred asks to be recognized) it also confers the rank of Papal legate to the King of Sicily, meaning great liberties in the appointment of Bishops and a larger degree of control over the local Church than in other contemporary realms.
 
In the long run, yes, controlling Germany, Burgundy, Italy and Sicily is a formidable challenge. But it's not impossible IMHO provided one breaks away from an anachronistic national state and views it more as an Austrian style primus inter pares, even if likely to end in a Charles V style partition with a younger branch getting Sicily. Think of how long England controlled Aquitaine, for instance. Given the Staufers are based out of Swabia and their longstanding southern ambitions it's likely that they would be heavily interested in Burgundy (Provence might well get annexed/integrated by marriage in place of the French connection of OTL) as well as Tyrol and OTL Switzerland which they own. OTL two families (the Zahringen and one other) died out in the 1220s, a strong Emperor could seize that land and Austria if/when the Babenbergs die out, even if the latter will probsbly be (partially) gifted to a Habsburg or some other Swabia retainer, a stronger more stable Emperor could use the opportunity to divide the lands.

Or Toulouse with Provence gets separated from French influence with Hohenstauffen help..

The Hohenstauffens do back the Counts of Toulouse in their claims to Provence.
 
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@Yanez de Gomera
I do agree that it would be possible to butterfly away some early deaths of the Hautevilles (and also Henry VI might survive, good point there). OTOH it is quite normal - given the medical science in the 12th and 13th centuries - that some early deaths occur in a royal family (even if there is quite a surprising cluster in the early 1190s, and after all the climate in Palermo is better than in northern Europe).
IMHO the critical death is Roger's one: if the heir survives and gets crowned king in 1194, there is no problem with succession (we obviously don't know if his marriage with the Byzantine princess will be fruitful, but there is still the spare wheel represented by his brother William, who should survive ITTL), and no need for a prolonged regency.

Why do you think that Henry VI would be still interested in making trouble in the south if Costanza dies before the marriage? I can understand the usual back and forth in the marches between the HRE and the Kingdom, but there should be no reason (and no need) for an outright invasion.

Agreed on the benefits of being a Papal Legate, if there is a strong (or at least a competent) king on the throne in Palermo. If there is a prolonged regency, or a weak king who cannot keep his nobles under check, the Church will move to increase their benefits and trim down the prerogatives of the kings of Sicily.
In the worst case, there is always the possibility that the pope grants the kingship to a different pretender even without an actual dynastic claim. It happened IOTL when the Anjous received the kingship, or later on when Aragon was invested with the kingdom of Sardinia, simply out of the blue. It also happened in a way when William the Conqueror received the Papal banner on the eve of the invasion of England.
 
@Yanez de Gomera
I do agree that it would be possible to butterfly away some early deaths of the Hautevilles (and also Henry VI might survive, good point there). OTOH it is quite normal - given the medical science in the 12th and 13th centuries - that some early deaths occur in a royal family (even if there is quite a surprising cluster in the early 1190s, and after all the climate in Palermo is better than in northern Europe).
IMHO the critical death is Roger's one: if the heir survives and gets crowned king in 1194, there is no problem with succession (we obviously don't know if his marriage with the Byzantine princess will be fruitful, but there is still the spare wheel represented by his brother William, who should survive ITTL), and no need for a prolonged regency.

Why do you think that Henry VI would be still interested in making trouble in the south if Costanza dies before the marriage? I can understand the usual back and forth in the marches between the HRE and the Kingdom, but there should be no reason (and no need) for an outright invasion.

I think Frederick I already tried to assert his sovereignty over Southern Italy some times, but failed because he had the greater and closer problem of having to fight against the Lombard cities. Henry seemed quite an ambitious ruler and could try something, especially if the throne falls to an illegitimate branch like Tancred's. On the other hand you are right that outright conquest without any hereditary claim seems quite iffy (and and POD in 1184 will also most likely butterfly away the train of events that lead to Richard of England's ransom enriching the HRE and at least partially financing Henry's expeditions against Sicily (BTW the first failed and it seems that the Kingdom only really collapses after Tancred's death - it might be possible to keep it separated from the Empire even with a very late POD such as Roger out living his father and having issue.

In the worst case, there is always the possibility that the pope grants the kingship to a different pretender even without an actual dynastic claim. It happened IOTL when the Anjous received the kingship, or later on when Aragon was invested with the kingdom of Sardinia, simply out of the blue. It also happened in a way when William the Conqueror received the Papal banner on the eve of the invasion of England.

Yes, that's a risk, but Charles d'Anjou was only invited at the climax of the decisive conflict between Papal and Imperial power and I'm a moment of great weakness for the empire and of shaky legitimacy for Sicily, since Manfred was illegitimate. And it could well have failed (in part it did, since after 1282 Sicily proper went back to an Hohenstaufen descendent (by female line, but still...), opening the way for the Wars of the Vespers and a separation between Sicily and mainland Italy that was imho never truly healed back).
 
I think Frederick I already tried to assert his sovereignty over Southern Italy some times, but failed because he had the greater and closer problem of having to fight against the Lombard cities. Henry seemed quite an ambitious ruler and could try something, especially if the throne falls to an illegitimate branch like Tancred's. On the other hand you are right that outright conquest without any hereditary claim seems quite iffy (and and POD in 1184 will also most likely butterfly away the train of events that lead to Richard of England's ransom enriching the HRE and at least partially financing Henry's expeditions against Sicily (BTW the first failed and it seems that the Kingdom only really collapses after Tancred's death - it might be possible to keep it separated from the Empire even with a very late POD such as Roger out living his father and having issue.
The Barbarossa had other fishes to fry in Northern Italy and in Germany, so I doubt he ever envisaged a strategy of conquering the south of Italy aside from the usual plotting in the areas around Benevento. Mounting up a campaign against the kingdom of Sicily would have required significant money, a good understanding of logistics and would have pinned him far away from the places where trouble was already occurring on a regular basis (and any bad news from the south of Italy would have sparked an insurrection in northern Italy or Germany; or most likely both). There is also the issue of the troubles in Outremer and the mounting up of the third crusade: an emperor who choose to make war against a christian king without a real claim and to the detriment of the crusade against the infidels would have found himself in a lot of troubles. Most likely Barbarossa strategy was to lead a successful crusade and on his return to take advantage of his clout and get rid of all rebellions.

Henry had a valid claim over the Sicilian crown, since Roger II had the barons swear fealty to Constance and him. Notwithstanding this, the conquest of the Kingdom was not an easy task, and as you say Henry had to mount two expeditions before being successful. IMHO if Roger (III) does not die at the ripe age of 19 and succeeds his father on the throne there is not a big chance that Henry can make good his claim.



Yes, that's a risk, but Charles d'Anjou was only invited at the climax of the decisive conflict between Papal and Imperial power and I'm a moment of great weakness for the empire and of shaky legitimacy for Sicily, since Manfred was illegitimate. And it could well have failed (in part it did, since after 1282 Sicily proper went back to an Hohenstaufen descendent (by female line, but still...), opening the way for the Wars of the Vespers and a separation between Sicily and mainland Italy that was imho never truly healed back).
As a matter of fact, the first invitation to Charles of Anjou dates back to 1248, and was put forward by pope Innocent IV: it went nowhere, also because of the opposition of the king of France. A second invitation was delivered under pope Urban IV in 1262, after the failure of the negotiations between the church and Manfred. This second invitation had a somehow better result (even if the French crown was not supportive), but the negotiations between the church and Charles were long since pope Urban IV wanted to make sure that the southern kingdom would never again become a threat to the papal states. Urban IV died, and another French pope was elected (Clement IV). More importantly Manfred woke up from his torpor and started to threaten the papal states and to meddle in Rome, in Tuscany and in Lombardy with the Imperial party. Finally Charles came to Italy, after managing to raise enough loans to finance the expedition, entered Rome and was proclaimed king of Sicily (in January 1266). Incidentally, there is a great POD in 1265: Charles was coming from Provence by ship with 1500 men but without horses. The Sicilian fleet blockaded the mouth of the Tiber and the access to Ostia, but the bad atmospheric conditions forced them to abandon the blockade and Charles could land without opposition on 21 May 1265. Better weather conditions might allow the Sicilian fleet to engage the ships of Charles with very good chances of success, or maybe a more decisive Manfred might play his cards better both in Rome during the election of the Senator or by sending troops to oppose the Anjou landing. As a matter of fact, the more I look into the matter the more I become convinced that good old Manfred frittered away his chances because of his indecision. He had almost 7 years to put his house in order and move decisively to link with the Northern Ghibellin party, and it should not have been impossible to secure the victory of the pro-Imperial faction in Rome. He never did this, and started to move aggressively when the political situation was almost compromised. I know that the deciding even was the battle of Benevento, but it shouldn't have been like that. Charles should have been stopped well before.

The illegitimacy of Manfred did not play a role in the events, other than providing a convenient fig-leaf for the machinations of the Roman Curia who was devoted to the emasculation of the southern kingdom and its detachment forever from the HRE. Even as late as 1263, one of the papal conditions was that besides Benevento most of coastal Campania (including Naples, Amalfi and other key cities) was to become part of the Patrimonium Petri directly governed by the church: this condition was later dropped because Manfred started to make threatening noises but other conditions (such as the king of Sicily could not hold imperial dignities, or become lord of Tuscany or Lombardy, and that the people of the kingdom were committed to depose the king if the pope found him guilty) remained.
 
The Barbarossa had other fishes to fry in Northern Italy and in Germany, so I doubt he ever envisaged a strategy of conquering the south of Italy aside from the usual plotting in the areas around Benevento. Mounting up a campaign against the kingdom of Sicily would have required significant money, a good understanding of logistics and would have pinned him far away from the places where trouble was already occurring on a regular basis (and any bad news from the south of Italy would have sparked an insurrection in northern Italy or Germany; or most likely both). There is also the issue of the troubles in Outremer and the mounting up of the third crusade: an emperor who choose to make war against a christian king without a real claim and to the detriment of the crusade against the infidels would have found himself in a lot of troubles. Most likely Barbarossa strategy was to lead a successful crusade and on his return to take advantage of his clout and get rid of all rebellions.

Henry had a valid claim over the Sicilian crown, since Roger II had the barons swear fealty to Constance and him. Notwithstanding this, the conquest of the Kingdom was not an easy task, and as you say Henry had to mount two expeditions before being successful. IMHO if Roger (III) does not die at the ripe age of 19 and succeeds his father on the throne there is not a big chance that Henry can make good his claim.




As a matter of fact, the first invitation to Charles of Anjou dates back to 1248, and was put forward by pope Innocent IV: it went nowhere, also because of the opposition of the king of France. A second invitation was delivered under pope Urban IV in 1262, after the failure of the negotiations between the church and Manfred. This second invitation had a somehow better result (even if the French crown was not supportive), but the negotiations between the church and Charles were long since pope Urban IV wanted to make sure that the southern kingdom would never again become a threat to the papal states. Urban IV died, and another French pope was elected (Clement IV). More importantly Manfred woke up from his torpor and started to threaten the papal states and to meddle in Rome, in Tuscany and in Lombardy with the Imperial party. Finally Charles came to Italy, after managing to raise enough loans to finance the expedition, entered Rome and was proclaimed king of Sicily (in January 1266). Incidentally, there is a great POD in 1265: Charles was coming from Provence by ship with 1500 men but without horses. The Sicilian fleet blockaded the mouth of the Tiber and the access to Ostia, but the bad atmospheric conditions forced them to abandon the blockade and Charles could land without opposition on 21 May 1265. Better weather conditions might allow the Sicilian fleet to engage the ships of Charles with very good chances of success, or maybe a more decisive Manfred might play his cards better both in Rome during the election of the Senator or by sending troops to oppose the Anjou landing. As a matter of fact, the more I look into the matter the more I become convinced that good old Manfred frittered away his chances because of his indecision. He had almost 7 years to put his house in order and move decisively to link with the Northern Ghibellin party, and it should not have been impossible to secure the victory of the pro-Imperial faction in Rome. He never did this, and started to move aggressively when the political situation was almost compromised. I know that the deciding even was the battle of Benevento, but it shouldn't have been like that. Charles should have been stopped well before.

The illegitimacy of Manfred did not play a role in the events, other than providing a convenient fig-leaf for the machinations of the Roman Curia who was devoted to the emasculation of the southern kingdom and its detachment forever from the HRE. Even as late as 1263, one of the papal conditions was that besides Benevento most of coastal Campania (including Naples, Amalfi and other key cities) was to become part of the Patrimonium Petri directly governed by the church: this condition was later dropped because Manfred started to make threatening noises but other conditions (such as the king of Sicily could not hold imperial dignities, or become lord of Tuscany or Lombardy, and that the people of the kingdom were committed to depose the king if the pope found him guilty) remained.

Oh you are right, Charles was really lucky and Manfred probably underestimated him too much (there is also the episode of Prencivalle Doris drowning in the Nera in 1264, just before reaching Spoleto and potentially capturing it. But that's a bit off topic...

An Hauteville dinasty that survives under the illegitimate branch of Tancredi di Lecce might be less friendly towards the Sicilian Muslims (he seemed to be more on the side of the Lombardy colonists in their disputes with the saracens in the Val di Mazara) but I don't think that the situation will become as bad as iotl, since there won't be a collapse of royal power like during the transition from Hauteville to Staufers and so we provably won't see something good like the deportation to Lucera. An organic Islamic populace in Sicily might survive for and lot longer, although not in great numbers, since their decline was already well underway.

Obviously the effects on any III crusade analogue are very intriguing: for example Cyprus seemed to be a Sicilian ally/vassal and I doubt the same chain of events can happen that lead iotl to the Lusignano rulers there.


Would a continued Hauteville Sicily being interested in recovering the Domain of Africa?
They most likely would, but it would also be extremely difficult to regain a foothold similar to the one they had under Roger II, at least until the disintegration of the Almohad Caliphate.
On the other hand a tributary relation is likely, since it happened iotl under the Hohenstaufen (Tunisia was really dependent on Sicilian grain to feed it's population).
 
Assuming Tancred's line survives and prospers - which is quite possible with a minimum of luck averting the death of Roger III - its destiny should be in the Mediterranean: Tunisia, Greece, and the ultimate plum: Egypt.
Which means that they should stay out of possible involvements in central and northern Italy and concentrate on keeping at least a protectorate over Tunisia as well as a presence on the coast of Libya. In other words, play the role of Aragon IOTL.
Ideally they would be allied with Aragon (God knows there were enough marriage links between them), although it is likely there will be some competition between them (as well as with Pisa, Genoa and Venice) over the eastern trade.
It would be great to see a Sicilian-Aragonese empire ruled from Palermo (say by the Hautevilles having a claim over the Aragonese throne and being able to enforce it during a succession crisis), but it looks like I'm asking for too much.

OTOH a surviving Manfred's line (which is very possible too) would almost certainly lead to an involvement in central and northern Italy, to the detriment of the Mediterranean strategy.

It is quite funny: if one looks for an Italian unification led by the south of Italy, rooting for Manfred might be the best bet. However I feel that the unification would result in a progressively reduction of the importance of Sicily (and the south) since the more rich and populous north would become more and more important.
If one wants to keep and increase the centrality of Sicily, the best way is rooting for Tancred.
 
Indeed. An Hauteville Mediterranean empire is rather interesting, but, if Sicily can remain relatively stable and prosperous, exploiting her strategic position to carve her "place in the sun" among Mediterranean powers (at the expense of Pisans and partially Aragon) it would be by far the strongest Italian state by the early XV century and who knows what could happen then? (With the added bonus of possible inheritances through marriage alliances which could give it an edge over Venice or Florence).
I doubt a union with Aragon would leave Sicilian interests at the helm... On the other hand Sardinia is a relatively easy prize (as long as she one has relatively good relations with the Pope) and a powerful bulwark against naval incursions from Imperial-aligned Pisa (or Genoa).

Egypt seems impossible to control, good trade relations on the other hand are quite possible...

As for Greece: some of it could already be taken in 1185, but the key is the fourth crusade: if something similar happens while Sicily is ruled by a somewhat capable king then very nice prizes are at hand and the Hautevilles seem more flexible in dealing with their Orthodox subjects than other Latins, also because they have a sizeable number of them in the Terra d'Otranto and Sicily.

Obviously it would be difficult to compete with first tier commercial powers like Venice and Genoa, but I don't think the kingdom is doomed never to develop an indigenous merchant class...

Whereas Manfred (as intriguing as he is as as person) would still have to contend with a powerful and hostile papacy: true, if he wins the Ghibellines would have the upper hand in Italy, for a time at least, but I really doubt him managing to formally extend his rule northwards.
 
A last bump, still hoping for some Byzantinophiles to join the discussion...

If there is no marriage and William II doesn't feel safe enough to have a great expedition against Rhomania for fear of Imperial encroachment what might he do with at least part of the navy and army he had already prepared by early 1185?

An invasion of Sardinia would make sense, there were many dynastic squabbles between the local Judikes/reguli and it could be seen as a useful base to control and possibly intercept naval expeditions coming from Pisa or Genua.

A more conservative option would be limited, mostly naval,operations in the East, possibly a capture of Corfu and generic piracy, since their Admiral Megareites/Margaritone was reportedly very skilled at it.
 
Forgot to say one of the sons of Andronikos can marry Constance..
Ah ok, this is a bit more plausible, but still, the Imperial marriage was a centerpiece of William's policy in the later part of his reign and a very good reason would be needed to change that. Besides, Constance probably lived in a convent until she was thirty and her marriage seemed to be a last resort to avoid the dinasty extinction (probably with the thought that she would have more than one male heir and therefore a personal union could be avoided.

A Greek king would never be accepted even if it didn't mean a return to Byzantine sovereignty.

To get a Roman marriage we need to get a bit back in time and marry William to Maria Komnene, the porphyrogenita, which could be interesting in itself. Marriages of a male Hauteville to a Byzantine princess are not unlikely, and the one between Roger of Lecce and Irene Angela is another promising one, but marrying the heir apparent to a potential future Basileus seems very very unlikely and would incur in all sort of troubles.
 
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