Isabella of Aragon (2 October 1470 – 11 February 1524), also known as Isabella of Naples, was by marriage Duchess of Milan and suo jure Duchess of Bari.

A member of the Neapolitan branch of the House of Trastámara, her life was characterised by the political crises surrounding the Italian Wars. Isabella often found herself torn between her native Kingdom of Naples and her marital home of the Duchy of Milan, causing her to suffer personal and political difficulties. After a disastrous marriage and lack of support in Milan, she received the Duchy of Bari as her personal property. This change in circumstances gave Isabella the opportunity to form her own court as well as build up political support and security against the ongoing wars. These reforms along with her interest in arts and literature, resulted in Bari undergoing revival and refurbishment. During this period, she also concentrated on the education of her daughter Bona, who became Queen of Poland.

Life Childhood and Family Isabella was born in the Kingdom of Naples, during the reign of her paternal grandfather King Ferdinand I of Naples. She was the second child of his heir, Alfonso, Duke of Calabria (who became King in 1494) and his wife, Ippolita Maria Sforza. Named after her paternal grandmother Isabella of Clermont (who died in 1465), the princess was educated at the residence of the Dukes of Calabria in Castel Capuano, and one of her teachers was the poet and humanist Giovanni Pontano. She was interested in music and poetry, and in her spare time she wrote some poems.

The only daughter from her parents' marriage, Isabella had two brothers: the elder was Prince Ferdinand (who would succeed their father to throne in 1495 but died one year later in October 1496) and the younger was Prince Piero (who was Lieutenant General of Apulia and Prince of Rossano, but died young of an infection following leg surgery on 17 February 1491). The siblings were raised alongside their cousins, the children of Eleanor of Naples, who included Isabella d'Este and Beatrice d'Este. Isabella had a particularly close relationship with the latter, developing into something of a sisterhood.

During her childhood, Isabella's parents had a difficult relationship, which was characterised by rivalry and contempt. Alfonso, perhaps threatened by Ippolita Maria's high level of education or disdainful of her pedigree, treated his wife with a lack of respect throughout the marriage. Alfonso preferred the company of his mistress, Trogia Gazzela, by whom he had two illegitimate children during Isabella's childhood. Her grandfather was a courageous ruler, who did not hold back when it came to dealing with his enemies. Being raised at this ruthless court in Naples certainly would have had an effect on Isabella, affecting her character as an adult.

From 1471, Isabella was planned to marry Gian Galeazzo Sforza, heir of the Duchy of Milan, and the preparations were concluded with the contract prepared on 26 September 1472. The bride and groom were first cousins (Isabella's mother and Gian Galeazzo's father were siblings), so a papal dispensation was needed, which was easily obtained from Pope Sixtus IV. On 30 April (or 1 May according to other sources) 1480 the betrothal was celebrated at the Castello di Porta Giova in Milan. In August 1488, the Sforza envoy Agostino Calco came to Naples to discuss the final details and the course of the ceremony. Calco's arrival coincided with the death of Isabella's mother, Ippolita Maria. Despite the period of mourning, King Ferdinand II of Aragon and Isabella's father decided not to postpone the wedding.

Marriage Wedding celebrations

In December 1488, the Milanese legation headed by the groom's brother Ermes, Marquis of Tortona went to Naples, where on 23 December, the marriage per procura took place. On 26 December, Isabella and her numerous entourage set off to meet her future husband. On 18 January 1489 she arrived in Genoa —there she rested before traveling to Tortona, where Gian Galeazzo was waiting for her. The meeting of the future spouses took place on 24 January. On 1 February, Isabella traveled from Vigevano to Milan, where the next day (2 February) the wedding ceremony was finally held in Milan Cathedral.

The ambassador Giacomo Trotti described Isabella on the occasion of the wedding: "the aforementioned new Duchess is a little dark-faced and not very beautiful, but she has a kind and beautiful person". Conversely, "the Duke is beautiful and very good".Archivio Storico Lombardo, serie quinta, anno XLVIII, Achille Dina, Isabella d'Aragona Duchessa di Milano e di Bari, p. 292.

Great celebrations followed the marriage. On 13 January 1490, in the Sala Verde of the Castello di Porta Giova, a masque or operetta entitled Il Paradiso, with a libretto by Bernardo Bellincioni was staged on the occasion of the wedding of Isabella with Gian Galeazzo. The scenography and costumes for the operetta were designed by Leonardo da Vinci. Despite the reports of ambassador Trotti, others praised Isabella for her beauty, like the Ferrarese ambassador who commented: "she was so beautiful and radiant that she seemed like the sun". The operetta was written very much with this praise for Isabella in mind. Il Paradiso was the representation of the seven planets orbiting round. A man portrayed each of the planets and all would speak praise of Isabella. Therefore, the operetta depicted Isabella as being at the centre of the universe. In addition to the acknowledgment of her physical appearance, Isabella was also noted for having an energetic personality; Gian Galeazzo, on the other hand, was quite a contrast to his wife; he was pale, studious and melancholy. The differences of personality would affect the marriage as well as in politics during the 1490s.

First years in Milan Soon after the wedding, the spouses moved against their will to Pavia, where Gian Galeazzo's uncle and Regent Ludovico Sforza prepared their seat. Isabella's relationship with her uncle was not going well. The Duchess, on the other hand, had a great liking for Ludovico's lover, Cecilia Gallerani. Isabella's marriage was also unsuccessful at first. After the wedding, Gian Galeazzo did not intend to consummate the union. In April 1490, reports of Isabella's continuing virginity even reached the Hungarian court to her aunt, Queen consort Beatrice of Aragon. After almost thirteen months, Gian Galeazzo began sexual relations with his wife, and Isabella became pregnant in May 1490. On 30 January 1491, during the wedding celebrations of Ludovico Sforza and Beatrice d'Este, Isabella gave birth to a son, named Francesco Maria in honour of both hers and her husband's grandfather Francesco I Sforza. This worried Ludovico, since the birth of the heir could made Gian Galeazzo and Isabella as potential figureheads for opposition to his position as Regent, which he was unwilling to relinquish. In order to weaken any coup attempts made by Isabella and her husband, Ludovico had her Neapolitan retinue returned home and restricted the young Duchess from appointing and rewarding followers.

Despite the initial good understanding between Isabella and Beatrice, soon aroused serious disputes over precedence: despite being the Duchess consort and thus the highest ranking woman at the Milanese court, Isabella was displaced by Ludovico's wife: Leonardo da Vinci was active in creating pageants and decorations in honour of Beatrice, and she was even given a political role, acting as ducal ambassador to Venice in 1493. In contrast, Isabella and her growing family were starved of household funds and she was forced to make petitions for allowance increases. It is of little surprise that she wrote to her father, asking him to intervene on her behalf. Ludovico used the Neapolitan connection to his advantage, portraying Isabella as working in the interests of her Neapolitan family or indeed in her own desire to dominate her husband and obtain power in Milan.

Over time, the conflict between Isabella and Ludovico, fueled by Beatrice d'Este, intensified. The Regent gave Isabella a gloomy and insecure chamber intended to discourage her from staying in Milan. He also took on the responsibility of educating Francesco Maria, isolating him from his parents. When attempts to talk with Ludovico did not help, Isabella made efforts to get closer to the Regent's wife, her cousin and childhood friend Beatrice, who in exchange for her help urged Isabella to remove from the court Ludovico's mistress, Cecilia Gallerani.

Isolation at the Milanese court

Relations with her husband, Gian Galeazzo, worsened. The Duke preferred the company of young men sent to him by his uncle over his wife and reprimanded her Milanese pastimes, and during the quarrels there were fights. In the fall of 1492, a scandal broke out when Isabella was accused of attempted murder. When the Duchess found out that Gian Galeazzo had a special affection for a lover called Rozone, she (perhaps out of jealousy towards her husband) urged the servants to poison not only the Duke's favorite but also Galeazzo Sanseverino, probably another lover, who was accused by Isabella of persuading the Duke to lead a life of debauchery. King Ferdinand I of Naples, informed on the matter, replied that it was impossible that Isabella had tried to poison Galeazzo, who was "loved by them as a son and always proved to be a good servant and relative"; as for Rozone, he justified the behavior of his granddaughter, saying indeed that he was surprised that "out of desperation" she had not done worse.Archivio Storico Lombardo, serie quinta, anno XLVIII, Achille Dina, Isabella d'Aragona Duchessa di Milano e di Bari, p. 331.

Ludovico used this incident to completely discredit Isabella, who since then lived in complete isolation —appearing only at official ceremonies. When on 26 January 1493, Isabella gave birth to a daughter, Ippolita Maria (named after her maternal grandmother the Duchess of Calabria), the event passed without publicity, because the day before Ludovico's son, Ercole Massimiliano was born, and this event was greeted by great pomp and ceremony, befitting an heir, something that had been denied to Isabella's son. On 2 February 1494 in Vigevano, the Duchess gave birth to another daughter, Bona Maria (named after her paternal grandmother Bona of Savoy).

Ludovico was now openly pursuing his ambition for absolute control over Milan. An important aspect of this was foreign policy, and his anti-Aragonese policy was far from favourable to Isabella or her Neapolitan family. In response to Ludovico's actions, Isabella's father had encouraged French ambitions over Milan. Understanding the weight of this threat, Ludovico severed diplomatic ties with the Neapolitan court and built an alliance with Maximilian I, Holy Roman Emperor. The reason for this particular alliance was that the Emperor had the power to grant the Dukedom to Ludovico. Meanwhile, Isabella and her husband found themselves confined to Castello Visconteo in Pavia, where they were essentially prisoners.

Ludovico encouraged Charles VIII of France to attack Naples and remove the threat of Isabella's father. When the French King arrived in the Duchy of Milan in October 1494, on his way to Naples, he was well received by Ludovico and Beatrice. Around this time, Isabella made a move and appealed to Charles VIII. She tearfully pleaded for the King to have mercy on her father; Charles VIII was embarrassed by Isabella's actions but he did have sympathy for her husband, who was dying. Isabella's pleading was in vain, the Italian Wars were underway and her father would be ousted from his throne by the French in 1495. In his infamous work The Prince, Niccolò Machiavelli blamed Ludovico for the devastation, claiming that he invited the French to attack Naples.