Siege of Messina (1282)

In the summer of 1282, Charles of Anjou began to muster his forces in southern Italy. Charles' plan was to cross the straits of Messina, take the city, and then use Messina as a beachhead to invade the rest of Sicily. While the Messinese organized their city's defenses, by June Charles had amassed 31,000 men and 82 ships in Catona, less than five miles away. Having lost a large number of ships when Messina drove out the Angevin garrison, Charles was forced to rely on a cobbled-together fleet of ships from his lands in Provence and southern Italy, supplemented by mercenary ships from Genoa, Pisa, and Venice. The Angevin army of 31,000 men, while large, was partially made up of feudal levies, who possessed limited combat experience and motivation. The first Angevin attempt to land on Sicily came on 2 June, when a force of 40 Angevin galleys attempted to make a landing north of the city before being forced to withdraw.^[2][1]

On 24 June a second Angevin landing attempt was made, succeeding in landing 5,500 Angevin troops near Milazzo, some twenty miles northwest of Messina. A force of Messinese militia was sent to counter this landing, but was engaged in battle and defeated, with over a thousand Mesinese casualties. The Angevins cut the coastal road running from Messina to Palermo via Milazzo, and the victorious Angevins marched south towards the city. In the aftermath of the defeat, Mussone was replaced as Captain of the People by Alaimo da Lentini. Lentini ordered the Messinese militias back behind the walls of the city, not wanted to risk further field battles with the Angevins.^[1]

In late July, Charles led the bulk of the Angevin army across the strait, making an uncontested landing four miles south of Messina. With an Angevin army pressing the city from the north, Charles and his army moved to surround the southern approaches to Messina. His encirclement of the city complete, Charles held a council of war to determine whether the city should be taken by storm or siege, ultimately deciding on the latter approach. The Angevin army of 31,000 men greatly outnumbered the Messinese garrison (which had at most 8,000 men), but Charles likely wanted to take the city and its vital port facilities intact. Charles was also aware that Messina had traditionally been a bastion of pro-Angevin support on Sicily, and so may have hoped to take the city without costly military action against the Messinese. Charles' forces burned the farmland on the outskirts of the city, hoping to starve Messina into submission, while his fleet blockaded the harbor.^[1]

With the Angevin encirclement of the city complete, both sides settled in for a siege. Charles began probing the Messinese defenses for weaknesses. He first attacked the Braccio di San Raineri, a sandy sliver of land that commanded Messina's harbor, but was unable to take a monastery the Messinese had fortified on the point. Unable to take the harbor, Charles re-oriented his assaults to capture the Monte della Caperrina, a prominent hill on the city's outskirts from which the Angevins could bombard the city with siege engines. Early attempts to take the hill by storm failed, as Lentini had ordered it fortified with trenches.^[1]

While the siege of Messina progressed, the political situation on Sicily remained uncertain. The newly formed Sicilian parliament was divided on what the political future of the island should be; one faction called for the island to seek the protection of the papacy, one wanted full Sicilian independence, while a third wanted to give the throne of Sicily to King Peter III of Aragon, whose wife Constance of Sicily was considered by some Sicilians to be the lawful heir to the Sicilian throne.^[2][3][4]

While the parliament debated, Messina remained under siege. In early summer, a papal envoy, Cardinal Gerardo da Parma, was allowed into the besieged city to negotiate with the Messinese. The defenders hoped he could be convinced to extend papal protection to the city; instead, Parma demanded the city surrender to Charles and delivered a papal censure to the Sicilian rebels, threatening further consequences if the city did not capitulate. The papal rebuke convinced many Sicilians to join the pro-Aragonese faction in the Sicilian parliament, which saw value in have Aragon as an ally against Angevin Naples. Peter of Aragon wanted to gain the Sicilian throne, and so in the summer of 1282 had sailed an army to the port of Collo in North Africa, using the prospect of a crusade as political cover. The Aragonese king landed his army of 8,600 men at Trapani on 30 August, marching on to Palermo to be crowned as King of Sicily. The Sicilian parliament crowned Peter as king on 2 September, and Peter began mustering an army to relieve Messina. While he ordered his main force to concentrate in the town of Randazzo, some 50 miles west of Messina, Peter sent an advanced force of 2,000 almogavars—elite infantrymen from the foothills of Aragon—and 500 crossbowmen as an advanced guard to disrupt the Angevin besiegers of the city. The advanced force, led by Sicilian exiles Niccola di Palizzi and Andrea da Procida, conducted a rapid advance to Messina, making the usual six-day trek in three days.^[3][5]

While Aragon moved, Angevin Naples remained mired in siege warfare in front of Messina. Aragon's arrival in the conflict complicated Charles' siege of Messina; while he had heard rumors of Aragonese intervention, and possibly had received direct confirmation that Aragonese envoys were on Sicily in late August, he did not immediately take action. On 2 September, Charles ordered another major assault on the Monte della Caperrina, but was repulsed again. On the night of 5 September, the advance Aragonese force of 2,500 men arrived outside Messina, and successfully established themselves in the foothills of the city, undetected by the Angevin army. Some of the Aragonese advanced even further and made it inside the city walls, a huge boost to the Messinese defender's morale. The next morning, the Messinese defenders launched their first counterattack since July; Messinese defenders sallied forth from the city gates, taking the Angevins by surprise, while Aragonese almogavars and light cavalrymen attacked from the high ground. The sally did major damage to the Angevin siege lines, killing several hundred Angevin soldiers and resulting in some siege engines and supplies being burned.^[3][5]

Despite the success of the Aragonese sally, Messina remained under siege. In addition, Charles of Anjou was now aware that Aragon had entered the war and had landed an army on Sicily. Realizing the need to capture Messina before the main Aragonese force under Peter arrived, or before the powerful Aragonese navy cut his lines of communication to Calabria, Charles began to prepare a major assault on the city. On 15 September, the Angevin army stormed the city walls in force, fighting a fierce battle with the Aragonese-Sicilian defenders before being forced to retreat. The assault was costly for the Angevins; hundreds of men were killed attempting the scale the walls of Messina, while an attempt by the blockading fleet to simultaneously capture the city's harbor ended in failure. Charles himself was almost killed by a Messinese ballista bolt, which instead killed two of his bodyguards. As the battered Angevin army withdrew from the walls, the Messinese garrison sallied from the city gates, inflicting further casualties on the Angevins.^[5]

Having failed to storm the city, Charles and his army withdrew several miles from the city walls. The Angevin army, though badly battered, still had some months of supplies left, and so Charles wanted to continue the siege. In an attempt to peacefully capture Messina, Charles sent an emissary to Lentini, offering a large sum of money and a general pardon for the Messinese if they surrendered, but Lentini dismissed this offer out of hand. On 16 September, envoys from Peter arrived at the Angevin camp, where Charles delivered an official rebuttal to Peter's claim on the Sicilian throne.^[5]

While Charles wanted to continue the siege, by mid-September the siege was becoming increasingly untenable. Angevin morale was low; Feudal levies that Charles had called into armed service were starting to see their contracts elapse, while the stockpiles of food brought to sustain the siege were depleted. In addition, news of the approach of the main Aragonese army bolstered the morale of the Messinese defenders, who now knew that the city was likely to be relieved. Acting on the advice of his war council, Charles decided to end the siege and evacuate his army across the straits of Messina. Charles and his court were able to make the crossing into Calabria without incident, but the large and unwieldy Angevin army was unable to evacuate quickly; rivalries between the hired Italian ships, the re-organization of supplies, and the size of the Angevin army all complicated the withdraw.^[5]

Observing the Angevin withdraw, the Aragonese-Sicilian defenders launched a series of raids against the Angevin siege lines, disrupting the Angevin army as it tried to withdraw. On 21 September, the garrison of Messina sallied forth in the evening, striking the remaining Angevin forces. The Aragonese advance penetrated the Angevin lines, burning ships and killing soldiers as they attempted to disembark onto the waiting ships. Hundreds of casualties were inflicted on the Angevins, and over a hundred watercraft were burned. Contemporary Catalan chronicles claimed that 2,500 Angevins were killed or captured in the attack, and that the light of the burning Angevin ships could be seen in Catona. By the end of September, no Angevin troops remained on Sicily.^[5]

Having successfully defended their city, the Messinese sent envoys to Peter. They found the royal army camped in Randazzo, where they informed Peter that the Angevins had been defeated and forced to withdraw. Peter and the Aragonese-Sicilian army arrived in Messina in late September, where Peter was received with a hero's welcome, his authority as king of Sicily greatly bolstered. In the weeks after the Angevin withdraw, the large and highly capable Aragonese navy harried the scattered Angevin fleet, defeating it in the Battle of Nicotera.^[3][5]

The failed siege of Messina was a major setback for Charles of Anjou and Angevin Naples. While the kingdom still possessed a formidable military, the failed military campaign in the summer of 1282 ended Angevin hopes of quickly crushing the Sicilian rebellion. Subsequent attempts by the Angevins to regain the strategic initiative in 1283 and 1284 ended in failure, and Angevin Naples would not land significant numbers of troops on Sicily until the Angevin invasion of 1298.^[5]