It is not needful to follow Duke Frederick in his military career. We may briefly remark that when he succeeded to Urbino by his brother's death in 1444, he undertook generalship on a grand scale. His own dominions supplied him with some of the best troops in Italy. He was careful to secure the good-will of his subjects by attending personally to their interests, relieving them of imposts, and executing equal justice. He gained the then unique reputation of an honest prince, paternally disposed toward his dependants. Men flocked to his standards willingly, and he was able to bring an important contingent into any army. These advantages secured for him alliances with Francesco Sforza, and brought him successively into connection with Milan, Venice, Florence, the Church of Naples. As a tactician in the field he held high rank among the generals of the age, and so considerable were his engagements that he acquired great wealth in the exercise of his profession. We find him at one time receiving 8000 ducats a month as war-pay from Naples, with a peace pension of 6000. While Captain-General of the League, he drew for his own use in war 45,000 ducats of annual pay. Retaining-fees and pensions in the name of past services swelled his income, the exact extent of which has not, so far as I am aware, been estimated, but which must have made him one of the richest of Italian princes. All this wealth he spent upon his duchy, fortifying its cities, drawing youths of promise to his court, maintaining a great train of life, and keeping his vassals in good-humour by the lightness of a rule which contrasted favourably with the exactions of needier despots.

While fighting for the masters who offered him condotta in the complicated wars of Italy, Duke Frederick used his arms, when occasion served, in his own quarrels. Many years of his life were spent in a prolonged struggle with his neighbour Sigismondo Pandolfo Malatesta, the bizarre and brilliant tyrant of Rimini, who committed the fatal error of embroiling himself beyond all hope of pardon with the Church, and who died discomfited in the duel with his warier antagonist. Urbino profited by each mistake of Sigismondo, and the history of this long desultory strife with Rimini is a history of gradual aggrandisement and consolidation for the Montefeltrian duchy.

In 1459, Duke Frederick married his second wife, Battista, daughter of Alessandro Sforza, Lord of Pesaro. Their portraits, painted by Piero della Francesca, are to be seen in the Uffizzi. Some years earlier, Frederick lost his right eye and had the bridge of his nose broken in a jousting match outside the town-gate of Urbino. After this accident, he preferred to be represented in profile—the profile so well known to students of Italian art on medals and bas-reliefs. It was not without medical aid and vows fulfilled by a mother's self-sacrifice to death, if we may trust the diarists of Urbino, that the ducal couple got an heir. In 1472, however a son was born to them, whom they christened Guido Paolo Ubaldo. He proved a youth of excellent parts and noble nature—apt at study, perfect in all chivalrous accomplishments. But he inherited some fatal physical debility, and his life was marred with a constitutional disease, which then received the name of gout, and which deprived him of the free use of his limbs. After his father's death in 1482, Naples, Florence, and Milan continued Frederick's war engagements to Guidobaldo. The prince was but a boy of ten. Therefore these important condotte must be regarded as compliments and pledges for the future. They prove to what a pitch Duke Frederick had raised the credit of his state and war establishment. Seven years later, Guidobaldo married Elisabetta, daughter of Francesco Gonzaga, Marquis of Mantua. This union, though a happy one, was never blessed with children; and in the certainty of barrenness, the young Duke thought it prudent to adopt a nephew as heir to his dominions. He had several sisters, one of whom, Giovanna, had been married to a nephew of Sixtus IV., Giovanni della Rovere, Lord of Sinigaglia and Prefect of Rome. They had a son, Francesco Maria, who, after his adoption by Guidobaldo, spent his boyhood at Urbino.

The last years of the fifteenth century were marked by the sudden rise of Cesare Borgia to a power which threatened the liberties of Italy. Acting as General for the Church, he carried his arms against the petty tyrants of Romagna, whom he dispossessed and extirpated. His next move was upon Camerino and Urbino. He first acquired Camerino, having lulled Guidobaldo into false security by treacherous professions of good-will. Suddenly the Duke received intelligence that the Borgia was marching on him over Cagli. This was in the middle of June 1502. It is difficult to comprehend the state of weakness in which Guidobaldo was surprised, or the panic which then seized him. He made no efforts to rouse his subjects to resistance, but fled by night with his nephew through rough mountain roads, leaving his capital and palace to the marauder. Cesare Borgia took possession without striking a blow, and removed the treasures of Urbino to the Vatican. His occupation of the duchy was not undisturbed, however; for the people rose in several places against him, proving that Guidobaldo had yielded too hastily to alarm. By this time the fugitive was safe in Mantua, whence he returned, and for a short time succeeded in establishing himself again at Urbino. But he could not hold his own against the Borgias, and in December, by a treaty, he resigned his claims and retired to Venice, where he lived upon the bounty of S. Mark. It must be said, in justice to the Duke, that his constitutional debility rendered him unfit for active operations in the field. Perhaps he could not have done better than thus to bend beneath the storm.

The sudden death of Alexander VI. and the election of a Della Rovere to the Papacy in 1503 changed Guidobaldo's prospects. Julius II. was the sworn foe of the Borgias and the close kinsman of Urbino's heir. It was therefore easy for the Duke to walk into his empty palace on the hill, and to reinstate himself in the domains from which he had so recently been ousted. The rest of his life was spent in the retirement of his court, surrounded with the finest scholars and the noblest gentlemen of Italy. The ill-health which debarred him from the active pleasures and employments of his station, was borne with uniform sweetness of temper and philosophy.

When he died, in 1508, his nephew, Francesco Maria della Rovere, succeeded to the duchy, and once more made the palace of Urbino the resort of men-at-arms and captains. He was a prince of very violent temper: of its extravagance history has recorded three remarkable examples. He murdered the Cardinal of Pavia with his own hand in the streets of Ravenna; stabbed a lover of his sister to death at Urbino; and in a council of war knocked Francesco Guicciardini down with a blow of his fist. When the history of Italy came to be written, Guicciardini was probably mindful of that insult, for he painted Francesco Maria's character and conduct in dark colours. At the same time this Duke of Urbino passed for one of the first generals of the age. The greatest stain upon his memory is his behaviour in the year 1527, when, by dilatory conduct of the campaign in Lombardy, he suffered the passage of Frundsberg's army unopposed, and afterwards hesitated to relieve Rome from the horrors of the sack. He was the last Italian Condottiere of the antique type; and the vices which Machiavelli exposed in that bad system of mercenary warfare were illustrated on these occasions. During his lifetime, the conditions of Italy were so changed by Charles V.'s imperial settlement in 1530, that the occupation of Condottiere ceased to have any meaning. Strozzi and Farnesi, who afterwards followed this profession, enlisted in the ranks of France or Spain, and won their laurels in Northern Europe.

While Leo X. held the Papal chair, the duchy of Urbino was for a while wrested from the house of Della Rovere, and conferred upon Lorenzo de' Medici. Francesco Maria made a better fight for his heritage than Guidobaldo had done. Yet he could not successfully resist the power of Rome. The Pope was ready to spend enormous sums of money on this petty war; the Duke's purse was shorter, and the mercenary troops he was obliged to use, proved worthless in the field. Spaniards, for the most part, pitted against Spaniards, they suffered the campaigns to degenerate into a guerrilla warfare of pillage and reprisals. In 1517 the duchy was formally ceded to Lorenzo. But this Medici did not live long to enjoy it, and his only child Catherine, the future Queen of France, never exercised the rights which had devolved upon her by inheritance. The shifting scene of Italy beheld Francesco Maria reinstated in Urbino after Leo's death in 1522.

This Duke married Leonora Gonzaga, a princess of the house of Mantua. Their portraits, painted by Titian, adorn the Venetian room of the Uffizzi. Of their son, Guidobaldo II., little need be said. He was twice married, first to Giulia Varano, Duchess by inheritance of Camerino; secondly, to Vittoria Farnese, daughter of the Duke of Parma. Guidobaldo spent a lifetime in petty quarrels with his subjects, whom he treated badly, attempting to draw from their pockets the wealth which his father and the Montefeltri had won in military service. He intervened at an awkward period of Italian politics. The old Italy of despots, commonwealths, and Condottieri, in which his predecessors played substantial parts, was at an end. The new Italy of Popes and Austro-Spanish dynasties had hardly settled into shape. Between these epochs, Guidobaldo II., of whom we have a dim and hazy presentation on the page of history, seems somehow to have fallen flat. As a sign of altered circumstances, he removed his court to Pesaro, and built the great palace of the Della Roveres upon the public square.

Guidobaldaccio, as he was called, died in 1574, leaving an only son, Francesco Maria II., whose life and character illustrate the new age which had begun for Italy. He was educated in Spain at the court of Philip II., where he spent more than two years. When he returned, his Spanish haughtiness, punctilious attention to etiquette, and superstitious piety attracted observation. The violent temper of the Della Roveres, which Francesco Maria I. displayed in acts of homicide, and which had helped to win his bad name for Guidobaldaccio, took the form of sullenness in the last Duke. The finest episode in his life was the part he played in the battle of Lepanto, under his old comrade, Don John of Austria. His father forced him to an uncongenial marriage with Lucrezia d'Este, Princess of Ferrara. She left him, and took refuge in her native city, then honoured by the presence of Tasso and Guarini. He bore her departure with philosophical composure, recording the event in his diary as something to be dryly grateful for. Left alone, the Duke abandoned himself to solitude, religious exercises, hunting, and the economy of his impoverished dominions. He became that curious creature, a man of narrow nature and mediocre capacity, who, dedicated to the cult of self, is fain to pass for saint and sage in easy circumstances. He married, for the second time, a lady, Livia della Rovere, who belonged to his own family, but had been born in private station. She brought him one son, the Prince Federigo-Ubaldo. This youth might have sustained the ducal honours of Urbino, but for his sage-saint father's want of wisdom. The boy was a spoiled child in infancy. Inflated with Spanish vanity from the cradle, taught to regard his subjects as dependants on a despot's will, abandoned to the caprices of his own ungovernable temper, without substantial aid from the paternal piety or stoicism, he rapidly became a most intolerable princeling. His father married him, while yet a boy, to Claudia de' Medici, and virtually abdicated in his favour. Left to his own devices, Federigo chose companions from the troupes of players whom he drew from Venice. He filled his palaces with harlots, and degraded himself upon the stage in parts of mean buffoonery. The resources of the duchy were racked to support these parasites. Spanish rules of etiquette and ceremony were outraged by their orgies. His bride brought him one daughter, Vittoria, who afterwards became the wife of Ferdinand, Grand Duke of Tuscany. Then in the midst of his low dissipation and offences against ducal dignity, he died of apoplexy at the early age of eighteen—the victim, in the severe judgment of history, of his father's selfishness and want of practical ability.

This happened in 1623. Francesco Maria was stunned by the blow. His withdrawal from the duties of the sovereignty in favour of such a son had proved a constitutional unfitness for the duties of his station. The life he loved was one of seclusion in a round of pious exercises, petty studies, peddling economies, and mechanical amusements. A powerful and grasping Pope was on the throne of Rome. Urban at this juncture pressed Francesco Maria hard; and in 1624 the last Duke of Urbino devolved his lordships to the Holy See. He survived the formal act of abdication seven years; when he died, the Pontiff added his duchy to the Papal States, which thenceforth stretched from Naples to the bounds of Venice on the Po.