Subscribe for ad free access & additional features for teachers. Authors: 267, Books: 3,607, Poems & Short Stories: 4,435, Forum Members: 71,154, Forum Posts: 1,238,602, Quizzes: 344

The Duke Valentino




The Duke Valentino had returned from Lombardy, where he had been to
clear himself with the King of France from the calumnies which had
been raised against him by the Florentines concerning the rebellion of
Arezzo and other towns in the Val di Chiana, and had arrived at Imola,
whence he intended with his army to enter upon the campaign against
Giovanni Bentivogli, the tyrant of Bologna: for he intended to bring
that city under his domination, and to make it the head of his
Romagnian duchy.

These matters coming to the knowledge of the Vitelli and Orsini and
their following, it appeared to them that the duke would become too
powerful, and it was feared that, having seized Bologna, he would seek
to destroy them in order that he might become supreme in Italy. Upon
this a meeting was called at Magione in the district of Perugia, to
which came the cardinal, Pagolo, and the Duke di Gravina Orsini,
Vitellozzo Vitelli, Oliverotto da Fermo, Gianpagolo Baglioni, the
tyrant of Perugia, and Messer Antonio da Venafro, sent by Pandolfo
Petrucci, the Prince of Siena. Here were discussed the power and
courage of the duke and the necessity of curbing his ambitions, which
might otherwise bring danger to the rest of being ruined. And they
decided not to abandon the Bentivogli, but to strive to win over the
Florentines; and they send their men to one place and another,
promising to one party assistance and to another encouragement to
unite with them against the common enemy. This meeting was at once
reported throughout all Italy, and those who were discontented under
the duke, among whom were the people of Urbino, took hope of effecting
a revolution.

Thus it arose that, men's minds being thus unsettled, it was decided
by certain men of Urbino to seize the fortress of San Leo, which was
held for the duke, and which they captured by the following means. The
castellan was fortifying the rock and causing timber to be taken
there; so the conspirators watched, and when certain beams which were
being carried to the rock were upon the bridge, so that it was
prevented from being drawn up by those inside, they took the
opportunity of leaping upon the bridge and thence into the fortress.
Upon this capture being effected, the whole state rebelled and
recalled the old duke, being encouraged in this, not so much by the
capture of the fort, as by the Diet at Magione, from whom they
expected to get assistance.

Those who heard of the rebellion at Urbino thought they would not lose
the opportunity, and at once assembled their men so as to take any
town, should any remain in the hands of the duke in that state; and
they sent again to Florence to beg that republic to join with them in
destroying the common firebrand, showing that the risk was lessened
and that they ought not to wait for another opportunity.

But the Florentines, from hatred, for sundry reasons, of the Vitelli
and Orsini, not only would not ally themselves, but sent Nicolo
Machiavelli, their secretary, to offer shelter and assistance to the
duke against his enemies. The duke was found full of fear at Imola,
because, against everybody's expectation, his soldiers had at once
gone over to the enemy and he found himself disarmed and war at his
door. But recovering courage from the offers of the Florentines, he
decided to temporize before fighting with the few soldiers that
remained to him, and to negotiate for a reconciliation, and also to
get assistance. This latter he obtained in two ways, by sending to the
King of France for men and by enlisting men-at-arms and others whom he
turned into cavalry of a sort: to all he gave money.

Notwithstanding this, his enemies drew near to him, and approached
Fossombrone, where they encountered some men of the duke and, with the
aid of the Orsini and Vitelli, routed them. When this happened, the
duke resolved at once to see if he could not close the trouble with
offers of reconciliation, and being a most perfect dissembler he did
not fail in any practices to make the insurgents understand that he
wished every man who had acquired anything to keep it, as it was
enough for him to have the title of prince, whilst others might have
the principality.

And the duke succeeded so well in this that they sent Signor Pagolo to
him to negotiate for a reconciliation, and they brought their army to
a standstill. But the duke did not stop his preparations, and took
every care to provide himself with cavalry and infantry, and that such
preparations might not be apparent to the others, he sent his troops
in separate parties to every part of the Romagna. In the meanwhile
there came also to him five hundred French lancers, and although he
found himself sufficiently strong to take vengeance on his enemies in
open war, he considered that it would be safer and more advantageous
to outwit them, and for this reason he did not stop the work of

And that this might be effected the duke concluded a peace with them
in which he confirmed their former covenants; he gave them four
thousand ducats at once; he promised not to injure the Bentivogli; and
he formed an alliance with Giovanni; and moreover he would not force
them to come personally into his presence unless it pleased them to do
so. On the other hand, they promised to restore to him the duchy of
Urbino and other places seized by them, to serve him in all his
expeditions, and not to make war against or ally themselves with any
one without his permission.

This reconciliation being completed, Guido Ubaldo, the Duke of Urbino,
again fled to Venice, having first destroyed all the fortresses in his
state; because, trusting in the people, he did not wish that the
fortresses, which he did not think he could defend, should be held by
the enemy, since by these means a check would be kept upon his
friends. But the Duke Valentino, having completed this convention, and
dispersed his men throughout the Romagna, set out for Imola at the end
of November together with his French men-at-arms: thence he went to
Cesena, where he stayed some time to negotiate with the envoys of the
Vitelli and Orsini, who had assembled with their men in the duchy of
Urbino, as to the enterprise in which they should now take part; but
nothing being concluded, Oliverotto da Fermo was sent to propose that
if the duke wished to undertake an expedition against Tuscany they
were ready; if he did not wish it, then they would besiege Sinigalia.
To this the duke replied that he did not wish to enter into war with
Tuscany, and thus become hostile to the Florentines, but that he was
very willing to proceed against Sinigalia.

It happened that not long afterwards the town surrendered, but the
fortress would not yield to them because the castellan would not give
it up to any one but the duke in person; therefore they exhorted him
to come there. This appeared a good opportunity to the duke, as, being
invited by them, and not going of his own will, he would awaken no
suspicions. And the more to reassure them, he allowed all the French
men-at-arms who were with him in Lombardy to depart, except the
hundred lancers under Mons. di Candales, his brother-in-law. He left
Cesena about the middle of December, and went to Fano, and with the
utmost cunning and cleverness he persuaded the Vitelli and Orsini to
wait for him at Sinigalia, pointing out to them that any lack of
compliance would cast a doubt upon the sincerity and permanency of the
reconciliation, and that he was a man who wished to make use of the
arms and councils of his friends. But Vitellozzo remained very
stubborn, for the death of his brother warned him that he should not
offend a prince and afterwards trust him; nevertheless, persuaded by
Pagolo Orsini, whom the duke had corrupted with gifts and promises, he
agreed to wait.

Upon this the duke, before his departure from Fano, which was to be on
30th December 1502, communicated his designs to eight of his most
trusted followers, among whom were Don Michele and the Monsignor
d'Euna, who was afterwards cardinal; and he ordered that, as soon as
Vitellozzo, Pagolo Orsini, the Duke di Gravina, and Oliverotto should
arrive, his followers in pairs should take them one by one, entrusting
certain men to certain pairs, who should entertain them until they
reached Sinigalia; nor should they be permitted to leave until they
came to the duke's quarters, where they should be seized.

The duke afterwards ordered all his horsemen and infantry, of which
there were more than two thousand cavalry and ten thousand footmen, to
assemble by daybreak at the Metauro, a river five miles distant from
Fano, and await him there. He found himself, therefore, on the last
day of December at the Metauro with his men, and having sent a
cavalcade of about two hundred horsemen before him, he then moved
forward the infantry, whom he accompanied with the rest of the men-at-

Fano and Sinigalia are two cities of La Marca situate on the shore of
the Adriatic Sea, fifteen miles distant from each other, so that he
who goes towards Sinigalia has the mountains on his right hand, the
bases of which are touched by the sea in some places. The city of
Sinigalia is distant from the foot of the mountains a little more than
a bow-shot and from the shore about a mile. On the side opposite to
the city runs a little river which bathes that part of the walls
looking towards Fano, facing the high road. Thus he who draws near to
Sinigalia comes for a good space by road along the mountains, and
reaches the river which passes by Sinigalia. If he turns to his left
hand along the bank of it, and goes for the distance of a bow-shot, he
arrives at a bridge which crosses the river; he is then almost abreast
of the gate that leads into Sinigalia, not by a straight line, but
transversely. Before this gate there stands a collection of houses
with a square to which the bank of the river forms one side.

The Vitelli and Orsini having received orders to wait for the duke,
and to honour him in person, sent away their men to several castles
distant from Sinigalia about six miles, so that room could be made for
the men of the duke; and they left in Sinigalia only Oliverotto and
his band, which consisted of one thousand infantry and one hundred and
fifty horsemen, who were quartered in the suburb mentioned above.
Matters having been thus arranged, the Duke Valentino left for
Sinigalia, and when the leaders of the cavalry reached the bridge they
did not pass over, but having opened it, one portion wheeled towards
the river and the other towards the country, and a way was left in the
middle through which the infantry passed, without stopping, into the

Vitellozzo, Pagolo, and the Duke di Gravina on mules, accompanied by a
few horsemen, went towards the duke; Vitellozo, unarmed and wearing a
cape lined with green, appeared very dejected, as if conscious of his
approaching death--a circumstance which, in view of the ability of the
man and his former fortune, caused some amazement. And it is said that
when he parted from his men before setting out for Sinigalia to meet
the duke he acted as if it were his last parting from them. He
recommended his house and its fortunes to his captains, and advised
his nephews that it was not the fortune of their house, but the
virtues of their fathers that should be kept in mind. These three,
therefore, came before the duke and saluted him respectfully, and were
received by him with goodwill; they were at once placed between those
who were commissioned to look after them.

But the duke noticing that Oliverotto, who had remained with his band
in Sinigalia, was missing--for Oliverotto was waiting in the square
before his quarters near the river, keeping his men in order and
drilling them--signalled with his eye to Don Michelle, to whom the
care of Oliverotto had been committed, that he should take measures
that Oliverotto should not escape. Therefore Don Michele rode off and
joined Oliverotto, telling him that it was not right to keep his men
out of their quarters, because these might be taken up by the men of
the duke; and he advised him to send them at once to their quarters
and to come himself to meet the duke. And Oliverotto, having taken
this advice, came before the duke, who, when he saw him, called to
him; and Oliverotto, having made his obeisance, joined the others.

So the whole party entered Sinigalia, dismounted at the duke's
quarters, and went with him into a secret chamber, where the duke made
them prisoners; he then mounted on horseback, and issued orders that
the men of Oliverotto and the Orsini should be stripped of their arms.
Those of Oliverotto, being at hand, were quickly settled, but those of
the Orsini and Vitelli, being at a distance, and having a presentiment
of the destruction of their masters, had time to prepare themselves,
and bearing in mind the valour and discipline of the Orsinian and
Vitellian houses, they stood together against the hostile forces of
the country and saved themselves.

But the duke's soldiers, not being content with having pillaged the
men of Oliverotto, began to sack Sinigalia, and if the duke had not
repressed this outrage by killing some of them they would have
completely sacked it. Night having come and the tumult being silenced,
the duke prepared to kill Vitellozzo and Oliverotto; he led them into
a room and caused them to be strangled. Neither of them used words in
keeping with their past lives: Vitellozzo prayed that he might ask of
the pope full pardon for his sins; Oliverotto cringed and laid the
blame for all injuries against the duke on Vitellozzo. Pagolo and the
Duke di Gravina Orsini were kept alive until the duke heard from Rome
that the pope had taken the Cardinal Orsino, the Archbishop of
Florence, and Messer Jacopo da Santa Croce. After which news, on 18th
January 1502, in the castle of Pieve, they also were strangled in the
same way.

Niccolo Machiavelli