Coins of Southern Italy
(Largely the Kingdom of Sicily and Naples)
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Byzantium
Constans II, with Constantine IV (641-668) 
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AU Solidus, 19mm, 4.34 gr.
In the 4th C Constantine moved the capital of Rome to Constantinople (Istanbul today). When the Western Empire fell to the Ostrogoths in the 5th C, Byzantium held territory on the Italian peninsula and in 535 Sicily came under Byzantium control. Much of this mainland territory was initially lost in the Lombard invasion but Sicily remained in Byzantine hands.
In 660 Constans moved the capital the the Byzantine empire back to the West and for 5 years Sicily (Syracuse) was capital of the empire, before this decision was reversed. This coin is linked to more to Constans II than Italy, but earns a place here since since he moved the capital (and it's a neat coin).
Constantine V, Leo III and Leo IV (751-775)
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AE Follis, 16x19mm, 2.52gr. Obv (from seller): "Constantine V, bearded left and Leo IV beardless right, standing facing, each wearing crown and chlamys, and holding akakia. Rev: Leo III, bearded, standing facing, wearing crown and chlamys, and holding cross potent." Mint is Syracuse.
Michael II (820-829)
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AE Follis,
18x20mm, 4.19gr. Obv (from seller): "Facing busts of Michael with short
beard (on l.) and Theophilus, beardless, both crowned, Michael wearing
Chlamys, his son loros. Rev: Large M with cross above and O beneath." Mint is Syracuse. SB
1652.
Byzantium experienced a resurgence in the 9th C and reacquired extensive territory in southern Italy, about the same time Sicily was succumbing to Arab pressure. Syracuse remained an important Byzantium outpost, but one increasingly vulnerable to the Arab threat. In 827, when the Byzantium admiral Euphemius revolted against the emperor, he called on Arab forces in north Africa to help him in his conflict. His goal was to become ruler of Sicily but he effectively opened the island to Islamic invasion. Sicily fell to the Arab invaders in 878, essentially establishing Arab dominance on the island. Fighting continued for almost 100 years and Messina fell in the 10th C. Fighting finally ended when the last mountain stronghold fell in 965.
Carolingian
Louis II of Italy (855-875)

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AR denier, 17mm, 1.1gr. Obv: +LVDOVVICVS INP, central cross over lines. Rev: +ANGILBERGA NP, central cross with eight rays. Mint is Benevento (It). R2013; MG 1178; Dep 10-F1, 141M (8 examples); MEC 1116; not in Prou. Note the cross potent, similar to Constans II above.
Louis II is descended from Louis the Pious via his son first Lothar. Lother I's inheritance from his father was the central Carolingian territory, running from the Low Countries through Burgundy down into Italy. When he died, his first son, Lothar, inherited the northern part of his father's lands, to be called Lotharingia, while his other son inherited Italy and ruled as Louis II.
At the time this coin was minted mainland Italy was subject to Arab raids and invasion. Disunity among the Italian princes made effective resistance difficult and the trade relationships coastal cities had with the Arabs made them less than enthusiastic to fight their Arab trading partners. Coastal communities were glad to see the Lombard hold on southern Italy weakened. Even the intervention of Louis II was unable to generate a sustained effort against the Arabs. It was only in the early 10th C that the Arabs were finally driven out of the mainland, although they continued to hold Sicily. In addition to the Arab threat, the Byzantium resurgence in this century caused attention to focus as well on the east coast of Italy, Byzantium's stronghold. Benevento fell to Byzantine forces in 891, who succeeded in holding it only for four years.
Kingdoms of Sicily and Naples
**
Maps from Loud, The Age of Robert Guiscard
At the start of the 11th century southern Italy was a cultural melange. Lombards controlled territory on the mainland, as did Byzantium. At the same time, Sicily was under Islamic control. Islamic forces were once against pressuring the mainland and raiding extensively, penetratring as far as Benevento in 1102. (Loud 29) In addition to the native Sicilians and Italians in the region, there was a significant Jewish population in southern Italy and Sicily. Most broadly, as Takayama (5) describes it, 'Thus, in the 11th century the Mediterranean world consisted of three major cultural zones: Latin-Christian Western Europe, Greek-Christian Byzantine East and Arab-Islamic north Africa and Spain. Southern Italy and Sicily formed their borders." However, Smith (32) notes "... in the passage of time, it became clear that these cultural traditions had mixed but never completely fused." This would set the stage for strife in the 12th C.
The Normans arrived in the south, on the mainland, in the second decade of the 11th C. They were drawn by pilgrimage and opportunity. Their military skills were utilized by both Greeks and Lombards and as time went on, their numbers increased and they began to carve out their own territory. They were both allies and enemies of the 11th C papacy. Out of this fluid political environment Robert Guiscard emerged as the dominant figure who was recognized as count of Apulia. As the Normans strengthened their hold on the southern mainland, their attention turned to Sicily. It is at this point that Roger I enters the picture.
Roger I: count of Sicily (d 1101)

AE Follaro, 12mm, .63gr. Obv from MEC: 'Arabic legend on three lines: 'bi-'l-amr al-maliki duriba,' or 'struck by royal command.'' Rev: circular arabic legend, central cross. MEC 14: 220, not in Biaggi.


AE Mezzofollaro, 16mm, 1.46gr. Obv: =OPERATO IN VRBE MESSANE, central ./REXW/SCoS. Rev: CONIATO PER ORDINE RE MAGNIFICO BRAMOSO DI ESSERE ESALTATO DA DIO. Mint is Messina. B 1233; Spahr 109.

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AE Follaro, 14mm, 2.14gr. Obv: lion's head. Rev: IL RE GUGLIELMO IL SECONDO, central Arabic text. Mint is Messina. B1232; MEC 432.

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Follaro, 12mm, 1.6gr. Obv: lion's head. Rev: IL RE GUGLIELMO IL SECONDO, central Arabic text. Mint is Messina. B1232; MEC 432-6.
William II
is son of William I, grandson of Roger II. His mother was Margaret of
Navarre and she was his regent during his minority. His reign was
characterized by conflict between competing Christian factions and
William's power was limited. William sponsored the Benedictine abbey at
Monreale, with the hope it would become a religious counterweight to
power concentrated by the bishop of Palermo. William's mother
encouraged the in-migration of Spanish and Norman knights and the
kingdom became increasingly Latinized. William himself was comfortable
with Greek and Arab culture, although Sicily as a whole was moving
towards the generalized Latin intolerance of Islam, a product of the
crusades. The fact that Jerusalem fell to Saladin in 1187 acerbated
Christian-Islam tensions in his lands.
Tancred of Sicily (1189
- 94)

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Follara, 6mm, 2.44gr. Obv in Arabic: KING TANCRED. Rev: +ROVERIVS, central REX. Mint is Messina. Spahr 139v (description by Berman).
Tancred is a first cousin of William II, nephew (illegitimate) of William I. He is an illegitimate son of Roger (died 1149) who in turn is a son of Roger II. Tancred had two sons who briefly claimed kingship of Sicily (Roger III, 1192 - 93 and William III, 1194) but neither appear to have had coinage. Tancred came to the throne during a conflict over succession, since William II died without an heir. Tancred was supported by a number of barons who recognized that any conflict over the throne would weaken the monarchy and thereby effectively shift power to them. Tancred had allies beyond Sicily in pursuing his claim. The alternate claimant was Henry of Swabia, husband of his aunt Constance. The pope was not enthusiastic about having a German presence both north and south of Rome, given his conflicts with the HRE, and therefore favored Tancred. It is possible the Byzantium also favored Tancred, who was culturally sympathetic to Greek ideas. Tancred died when he was only 39 and the throne passed via his aunt to German control.
Tancred had a hard reign. He found himself the unfortunate host of Richard the Lion Hearted and Philip August who stopped (and looted) in Sicily on their way to the Holy Land during the Third Crusade. This visit was complicated by the fact that Richard's sister, Joanna, was the widow of William II, and Richard claimed that her dowry should be returned since William died. This six month visit contributed to the erosion of Tancred's authority, as did the constant opportunistic pirate raids on the Sicilian coast during his reign. He also lost authority to the Church, which was able to assert ecclesiastical control it has not been able to exercise under earlier rulers.
Henry VI (of Swabia) (1194-97)and Constance
d'Altavilla (1195-98)

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Denero 13mm, .46gr. Obv: E.NPERATOR, central cross. Rev: C.INPERATRIX, central eagle. Mint is Brindisi. Biaggi 433.
Constance was a daughter of Roger II and sister of William I and aunt of William II. She became queen of Sicily in 1195, after the death of Tancred and his sons. She married Henry of Swabia, which took the line out of direct Norman control and passed it to the Germans. Henry was son of Barbarosa, who died on the Third Crusade. Whereas as the Normans had Sicily as their central focus, Henry saw it as an incidental part of of his German territories. He essentially looted Sicily and carried its treasures back to Germany. Henry and Constance died within a year of each other aqfter a short reign and left a very young Frederick II as their heir. He had to rely on the papacy protection, which turned out to be fairly ineffective, given the limited resources of the papacy and the rapaciousness of the German nobles who had settled in Sicily. Henry's greatest legacy was the intorduction of Germanic influence and Germanic nobility into Sicily. Neithyer seemed to serve Sicily well.
Henry VI (of Swabia) and Frederico
(1196)
king of Rome

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Denero, 15mm, .61gr. Obv: + E INPERATOR, central facing head. Rev: +FREDERIC'REX, central eagle. Biaggi 436.

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Denero, 16mm, .69gr. Obv: +ROM.NPERATOR, central F with three stars. Rev: +.R.IERSL'.ET.SICIL', central cross with four stars. Mint is Brindisi. Biaggi 473.
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Conrad I (1250-54)

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Denero 13mm, .52gr. Obv: +CONRADVS, central cross. Rev: JERRL'ET .SICL'., central large R. Mint is Brindisi. Biaggi 475.
Conrad was son of Frederick II, HRE. In Sicily he was Conrad I, but via other German titles he was known as Conrad IV. His reign was short and ineffective and he never really established control over Sicily. This was a time of turmoil for the island, as it came into political play more dramatically than during Frederick's life. Frederick had been excommunicated and the pope was looking for someone other than a direct Hohenstaufen to take the throne. It was offered to Alponse of Spain (who declined) and Richard, Earl of Cornwall, who also declined. He responded along the lines, says Benjamin (206) "it was like being offered the moon, provided he could take it from the sky." Charles of Anjou also initially declined and final it was accepted by Edmund, a son of English king Henry. However the English never paid the pope nor tried to exercise the claim and the offer was subsequently rescinded. While Conrad's reign was short, he had quite a varied coinage. Here are several more examples.

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Denero 13mm, .53gr. +IERVSLEM, central COR. Rev: +ET SICIL 'REX., central cross. Mint is Brindisi. Biaggi 476.
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Billon denero, 16mm, .58gr. Obv: +CONRADVS, central cross. Rev: +IERL'ET.SICIL', central REX or RE omega. Mint is Messina. B 1269; MEC 579-80.
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Billon denero, 15mm, .5gr. Obv: +CONRADVS, central cross. Rev: +IERL'ET.SICIL, central REX or RE omega. Mint is Messina. B 1269.
Conrad (Conradin) II (1254-68)

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Denero 13mm, .67gr. Obv: +MANFRIDVS, central eagle. Rev: +.REX.SICILIE, central cross. Mint is Messina. Biaggi 1275.
Manfred is an illegitimate son of Frederick II, HRE and brother of Conrad I (died 1254). He was crowned in Palermo in 1258 and was the de facto ruler of Sicily, regardless of the claim of his nephew Conradin. He functioned both as a regent and king. I'm not aware of how succession was planned. Manfred had support in Sicily and hostility from the pope. The Sicilians saw him as a proponent of Sicilian nationalism and someone familiar with their culture and traditions. He was successful in exerting control over Sicily and extending it to the southern Italian peninsula. By this time the papacy was help by Urban IV, a Frenchman. After the previous failed efforts to get an Englishman on the Sicilian throne, Urban turned again to Charles of Anjou, brother of the king of France. This time around, Charles was more interested in the prospect of his own kingdom and accepted the Urban's offer of the crown. Charles entered Italy with papal support and a large army to pursue his claim. He and Manfred met near Benevento in 1266 and defeated him in combat. Manfred was killed in this battle.
While king, in about 1259, Manfred married his daughter (Constance) to Peter of Aragon, heir to that throne. This marriage opened the door to Sicily for the Aragonese after the revolt of the Sicilian Vespers.
Charles of Anjou/ Charles I of Sicily (1266 - 85) 
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Denier, 19mm. Obv: K COMES PROVINCIE,
central monogram. Rev: +FIL_REGIS FRANCIE, cross with two besants, one
lis and one ?. R4124, not clearly in Boudeau but obv same as 814, not in
Bel.
Charles had territorial interests in both Italy and Provence. He received a papal offer of the crown of Sicily from Urban IV.
Popes propose but others contest. In Italy Charles ran into problems. He manipulated the execution of Conradin, successor to Barbarossa and Frederick II and heir of king Manfred. His death angered the Italians, who held no love for the French. The French imposed strict controls over Italian territories, rankling the local populace. In response to an instance of French abuse, particularly the supposed abuse of a Frenchman (soldier?) of a Sicilian woman on March 30, 1282, the citizens of Palermo rose against the French, slaughtering thousands. This episode is referred to as the night of the Sicilian Vespers. This revolt in Palermo quickly spread throughout Sicily and ultimately led to a complete French withdrawal from the island. Charles had to defend his nearby territories on the mainland. Charles made his headquarters in Naples and the island and mainland began to have significantly different experiences. Sicily soon fell under Aragon's control and turned to Spain while the peninsula remained focused on the papacy and north. Sicily lost access to the university in Naples, which weakened the educational base of the island.
This conflict in Sicily was further complicated by the fact that the next pope (Nicholas III) sought greater control over Italy than his predecessor had exerted. Nicholas wanted to rule Italy himself. In a negotiation with the Hapsburgs (who were papal allies at the time) and Charles, Charles was to relinquish Sicily in return for the kingdom of Arles and Vienne. (The crown would actually go to his heir - Charles the Lame.) After the episode if the Sicilian vespers Charles no longer had Sicily to relinquish. However, he was prepared to fight to regain it.
After Charles' death Sicily goes to Aragon.
Charles,
being of royal blood, was
entombed in St. Denis outside of Paris, burial place for the French
kings.
This is the effigy from his tomb.

Charles II of Anjou (1285-1309)

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Denero gherardino, 13mm, .52gr. Obv: +ROBERTV.DEI.GRA, central four lis-like elements. Rev: +IERL.ET.SICIL'.REX, central cross. Mint is Naples. Biaggi 1637.
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AR denero, 15mm, .47gr. Obv: +DE ANCONA. central cross. Rev: +.PP.S.QVI.R.I.A, central CVS. Biaggi 33v. See also B 42-44. This reverse punctuation does not match any of the Biaggi citations.
Federico il Semplico (1355-77)

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AR Pierreale, 24mm, 3.26gr. Obv: +FRIDERICVS:DEI:GRA:REX.SICILIE, central eagle. Rev: +AC AThENAR:2:NEOPATRIE:DVX, central shield of Aragon. Mint is Messina. B 1319; Sp 210.Alphonso 1, Kingdom
of Sicily (1415-58)

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Billon denero, 15mm, 72g. Obv: +ALFONS:D:GR, central eagle. Rev: REX SICILI, cross on shield of arms. Mint is Messina. Biaggi 1349.
Sources:
Astarita, T., Between Salt Water and Holy Water, Norton, N.Y., 2005
Benjamin, S., Sicily: Three Thousand Years of Human History, Steerforth Press, N.H., 2006
Finley, M.I., Smith, D.M. and Dugan, C., A History of Sicily, Viking, N.Y., 1987
Loud, G.A., The
Age of Robert Guiscard, Longman, London, 2000.
Smith, D.M., A History of Sicily: Medieval Sicily (800 - 1713), The Viking Press, N.Y., 1968
Takayama, H., The
Administration of the Norman Kingdom of Sicily, EJ Brill,
N.Y., 1993