1499: Paolo Vitelli, duplicitous commander

Add comment October 1st, 2018 Headsman

On this date in 1499, Florence decapitated its chief general for dereliction of command.

Paolo Vitelli, a noted condottiero whose family had taken over Citta di Castello, was hired by the post-Savonarola Florentine Republic during the Italian Wars to campaign against Florence’s traditional rival, Pisa.

“If this man had taken Pisa, nobody can deny that it would have been proper for the Florentines to keep in with him,” mused Machiavelli years later in The Prince. “For if he became the soldier of their enemies they had no means of resisting, and if they held to him they must obey him.”

The prospective kingpin made fantastic progress against the Pisans, and when news reached his Florentine patrons that Vitelli had taken a key gate in Pisa’s walls, the city smugly began drawing up wishlists of humiliations to heap upon the vanquished. But at the critical moment, “just when the whole army, and especially the youthful Florentines who had joined the camp as volunteers, were carrying all before them by their indomitable ardour, they were suddenly ordered to retreat. And Paolo Vitelli, seeing the unwillingness of the soldiers to obey, rushed among them with his brother Vitellozzo* and drove them back with blows.”

As jaws hit tables all around Florence, Pisa’s defenders were hurriedly patching the breach and retrenching. The attackers had ransacked their treasury to finance the expedition; there was nothing for a do-over. Had Vitelli quailed, or was he playing some double game? Either way, Machiavelli lamented — contemporaneously this time, in his capacity as an emissary of state — “We should have preferred defeat to inaction at so decisive a moment.”

With mingled urgency and circumspection, Florence’s leaders arranged to invite Vitteli to a war council at which he was arrested. Interrogated on September 30th, he was beheaded the very next day.

* Three years later, Paolo’s brother Vitellozzo would also achieve the pages of Executed Today … and once again did so under the sharp eyes of Machiavelli.

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1513: Pietro Boscoli and Agostino Capponi, but not Niccolo Machiavelli

Add comment February 23rd, 2015 Headsman

Niccolo Machiavelli‘s exile from Florentine politics — and subsequent entry into the intellectual canon — was cinched this date in 1513 when two of his friends (or possibly co-conspirators) were executed for a plot against the Medici.

Before he was an adjective, Machiavelli was a powerful minister of state for the Florentine Republic — the polity ensuing the 1498 execution of Savonarola.

Days after that stern friar burned to ashes on the Piazza della Signoria, Machiavelli was named the secondo segretario fiorentino,* alongside a primo segretario counterpart, the older and more cautious Marcello Virgilio Adriani.

What a moment this was to be a Florentine! The mighty Medici had been chased out of Florence and with the fall of Savonarola and his grim morals police the humanist dream of a classical republic suddenly seemed within grasp.

Machiavelli was just 29 years old when he reached this office, bursting with a patriot’s reckless exuberance — and a virile young man’s hedonism. He delighted in whores and in boozing around with his Chancery cronies Agostino Vespucci** and Biagio Buonaccorsi.

The correspondence of these indiscreet young Turks fill with profane and cutting takes on the leading citizens of Florence; Machiavelli, who was known in his own time as a playwright and not a political philosopher, was even bold enough to put such ridicule in print. The 1504 play Le Maschere is tragically lost, but by surviving accounts it lampooned “under feigned names, many citizens who were still living.”†

A few books about Niccolo Machiavelli

While not scribbling pasquinades and getting laid, the Second Secretary had matters of state to attend to. We have met him in these pages, as the Florentine ambassador to the court of Cesare Borgia; Machiavelli could not help but admire the condottiero‘s ruthlessness. Machiavelli also represented Florence in Rome, Spain and France.

Showing an equal aptitude for politics by other means, Machiavelli moved the Florentine military muscle towards a citizen militia, presciently replacing its dependence on mercenaries. In 1509 this force captured Pisa.

But Machiavelli’s excessive regard for this strategic advance married to his excessive affinity for the republic of Piero Soderini undid him in the end. While the First Secretary, Adriani, quietly cultivated contacts of various political persuasions, Machiavelli went all in against the stirring Medicean party. This became a problem when the fortunes of peninsular war drove Florence’s French allies away, leaving the city ripe for recapture by Giuliano de’ Medici, who also happened to be the brother of the pope in waiting.

In 1512, a hastily-assembled city militia of about three or four thousand infantry and 100 men-at-arms met an overwhelming Spanish-Papal-Medicean force at Prato. Scrambling to defend a lost cause, Machiavelli had mustered about a third of the militia and was trying to organize the city’s defenses. Florence’s crushing defeat in this battle and the ensuing civic massacre in Prato (with “countless murders, sacrileges and rapes”) convinced the Florentines to depose Piero Soderini and throw open the gates to Giuliano de’ Medici.

This was the end of Machiavelli the statesman … and, of course, the birth of Machiavelli the philosopher. The ensuing 15 years’ frustrating exile left him no other outlet for his political passions save his pen; needless to say, works like The Prince and Discourses on Livy retain exalted seats in the canon down to the present day. (They made little impression on Machiavelli’s contemporaries; Florentines still knew him for the plays he kept writing.)

A few books by Niccolo Machiavelli

When evening comes, I return home and enter my study; on the threshold I take off my workday clothes, covered with mud and dirt, and put on the garments of the court and palace. Fitted out appropriately, I step inside the venerable courts of the ancients, where I nourish myself on that food that alone is mine and for which I was born; where I am unashamed to converse with them and to question them about the motives for their actions, and they, out of their human kindness, answer me. And for four hours at a time I feel no boredom, I forget all my troubles, I do not dread poverty, and I am not terrified of death. I metamorphose into them completely.

-Machiavelli, December 10, 1513

The cautious primo segretario Adriani, who could better see where the winds were blowing, survived the transition by having the wisdom not to align himself with the losing party. Whatever the verdict of posterity, the 1510s were Adriani’s time to bask in the center of events while Machiavelli did his work of ages in obscurity.

But what cinched Machiavelli’s unhappy permanent banishment from Florentine politics — notwithstanding unctuous expedients like dedicating The Prince to the Medici ruler — were the events culminating in two February 23, 1513 beheadings.

Machiavelli had been dismissed in November 1512. Four months later, a nascent (or wildly exaggerated) anti-Medici conspiracy led by a republican named Pietro Boscoli came to light. Its chief, and paltry, evidence was little more than a written list of around 20 fellow-travelers, upon which appeared the name of Niccolo Machiavelli. It’s more than likely that the “treason” comprised merely to the idle chatter of some disaffected republicans, but after a generation in exile the newly restored Medici dynasty wasn’t taking any chances.

For the onetime Second Secretary, this meant prison and torture by the strappado. Three months on, he was released to his estate with no political succor save the haunts in his head.

But the head he got to keep — and that was better than one could say for Pietro Boscoli.

Boscoli and one Agostino Capponi were beheaded early in the morning of February 23, a bare eight hours after their death sentences were announced. Their last hours were recorded as a Recitazione by a young friend named Luca della Robbia: the tender Passion scene of Boscoli in particular struggling to come to grips with his shockingly sudden fate. The full narrative can be found in translation by Alison Knowles Frazier in The Art of Executing Well: Rituals of Execution in Renaissance Italy. We excerpt a little taste below:

At about 8 o’clock, having had his supper, Boscoli was brought with his legs in irons to the chapel where … he was told that he had to die …

Pietro Paolo cried out “Oh Pietro Paolo, oh poor Pietro Paolo! What has become of you!”

Then I, moved by the greatest compassion, seeing my beloved friend in such great distress, went first to him as lovingly as I could, with a gesture full of mercy, and greeted him like this: “God save you, dearest friend. ‘Do not fear those who kill the body, for they cannot kill the soul.’

Poor Pietro Paolo struggles on here for 15-odd pages in evident anguish, veering between practical considerations of the family he is leaving behind and whom to rustle up as his last-minute confessor, and his uncertain spiritual readiness for death (he was particularly upset at being told of his fate after dinner, for “I am too loaded down with food, and I have eaten salty things, so that I don’t feel able to join my spirit to God”). Della Robbia stays with him the whole time; in the latter’s introduction, he says he “noted diligently all his words, both questions and replies, and kept them in my memory … that such a great and well-formed example of strength and spiritedness would not be lost” and recorded them faithfully later on.

By the end, Boscoli has reconciled his mind to the scaffold.

He is escorted down the stairs from the chapel of the Bargello to its interior courtyard where

leaving the first step, he encountered the Confraternity’s‡ crucifix.

“What am I to do?” [Boscoli] said.

“This is your captain, who comes to arm you,” the friar responded. “Greet him, honor him, ask him to make you strong.”

Then he said, “Greetings, Lord Jesus. I adore you, hanging on the cross. Make me, I beg you, like to your Passion. True Lord, I ask you for peace.”

And thus, going down the second step, he kept commending himself, saying, “‘Into your hands, Lord, I commend my spirit. You redeemed me, Lord, God of truth.’” When he was on the little platform of the stair, he said, “Is it enough, a good preparation towards God? For I feel some battle. Recall to me those three things.”

Then I, who was behind him, said, “Well you know that it is enough. Say to him, Fra Cipriano, that verse by David, ‘Your ear heard the preparation of their heart, Lord.’

“Okay, yes,” the friar replied, “Your ear heard the preparations …,” and told him once again the three things.§

And he answered, and said, “‘Let your ear hear the preparation of my heart, Lord Jesus.'”


Then the executioner, because he wanted to put a kerchief over his eyes, asked his forgiveness and offered to pray to God for him.

“Go ahead and do your duty,” Pietro Paolo said. “And when you have put me at the block, leave me like that for a bit and then finish me off, and that you pray God for me, I accept.”

The reason why he asked for a little time at the block, was that he had all night long always desired a great joining with God and he didn’t feel that he had achieved it as he desired, so that he hoped in that last moment to make a great effort and so to offer himself wholly to God …

And placing himself down, and the executioner, giving him the shortest time, cleanly removed his head, which, so cut, continued to move its mouth for a time.

Agostino Capponi, whom della Robbia has seen only glancingly over his long narrative, follows Boscoli. Although Capponi required two blows of the executioner’s blade, he perhaps went into the hereafter with a soul better at peace — for he “retained on his face a certain wry expression, perhaps not distant from true sincerity.”

* Summary of Machiavelli’s career based on William Landon’s Politics, Patriotism and Language: Niccolò Machiavelli’s «Secular Patria» and the Creation of an Italian National Identity.

** Machiavelli’s clerk Agostino Vespucci — a cousin of the explorer Amerigo Vespucci for whom the American continents were named — made the headlines recently when discovery of a scribble he left in the margin of a 16th century text established the identity of the long-mysterious first lady of Renaissance art, Mona Lisa: she was Lisa del Giocondo, the wife of a Florentine cloth merchant.

† Landon says the primo segretario Adriani encouraged Machiavelli to publish this play, even though Adriani himself is one of its targets — in Landon’s view, because Adriani was playing a long game for power, and revenge: quietly encouraging Machiavelli’s excesses while positioning himself politically to profit from his consequent fall.

‡ The Confraternity of the Blacks: a lay brotherhood associated with Florence’s [former] Chiesa di Santa Maria Vergine della Croce al Tempio, tasked with the spiritual assistance of prisoners condemned to death.

§ Shortly before proceeding to execution, Boscoli steeled himself for the ordeal by resolving that “In this journey I have to have three things. I have to believe the faith. I have to have firm hope that God will pardon me. And the third is that I have to suffer this death for love of Christ and not for others.”

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1477: Gerolamo Olgiati, ducal assassin

Add comment January 2nd, 2015 Headsman


Dramatization of events in this post for the video game-derived film Assassin’s Creed: Lineage.

On this date in 1477, the assassins of the Duke of Milan suffered bitter death for fame eternal.

Famous for both his astute political machinations and for cruelty verging on the sadistic, Galeazzo Maria Sforza inherited leadership of Milan in at the age of 22 with the passing of his father, the great condottiero Francesco Sforza.

Francesco, the founder of the Sforza dynasty, had dynastically married himself to one Bianca Maria Visconti, a daughter of Milan’s previous ruling house.* But not all of the Visconti were at home with the Sforza.

A brash young man of that noble family, Carlo Visconti, as full of humanistic idealism as he was of bile for the licentious Duke’s alleged violation of his sister, joined a conspiracy also compassing two other gentlemen, Giovanni Andrea Lampugnani and Gerolamo Olgiati, to do Galeazzo Sforza to death.

At a St. Stephen’s Day service in a basilica christened to Stephen Lampugnani approached the prince feigning supplication for some audience, then produced a hidden blade and stabbed Galeazzo Sforza. Visconti and Olgiati then rushed on Sforza as well and before anyone realized what was happening the Duke, croaking some half-heard invocation of Mary, was falling dead on the church floor.


Illustration of Galeazzo Sforza’s murder on the title page of a 1476 Lament for the Duke decrying the assassination.

Pandemonium ensued, and in the ensuing helter-skelter, Sforza’s bodyguards fell on Lampugnani and killed him on the spot, while Olgiati managed to escape.**

“It now only remains for us to consider those dangers which follow after the execution of a plot,” Machiavelli mused in his “Of Conspiracies” typology of his Discourses. “These in fact resolve themselves into one, namely, that some should survive who will avenge the death of the murdered prince. The part of avenger is likely to be assumed by a son, a brother, or other kinsman of the deceased.”

Well, yeah.

The assassins of the Duke of Milan appear not to have burdened themselves overmuch with advance consideration of this danger, possibly indulging the dream of Brutus that by a dagger’s stroke alone they could restore the lost republic.

Needless to say, this beautiful hope vanished in the bloody revenge carnival that actually ensued the murder. Just a few days after the assassination, having taken refuge with a priest — his justly frightened family had closed its door on him and needed to make theatrical denunciations of his treason for their own safety — Olgiati was captured, put to a torturous interrogation, and publicly butchered. He had outlived the Duke by only a week, and his gashed carcass was hung up in sections around town by way of warning. The rotting heads of the conspirators remained impaled on lances on the city’s bell tower well into the 1490s.

According once again to Machiavelli, Olgiati “exhibited no less composure at his death than resolution in his previous conduct, for being stripped of his apparel, and in the hands of the executioner, who stood by with the sword unsheathed, ready to deprive him of life, he repeated the following words, in the Latin tongue, in which he was well versed

“‘Mors acerba, fama perpetua, stabit vetus memoria facti.'”

That is,

‘Death is bitter but fame is eternal, and the memory of the deed will endure.’

This attempt, quixotic and doomed, to depose an Italian tyrant by murdering him in church might well have formed the blueprint for a similar plot in Florence in 1478, the Pazzi conspiracy. That version was even less successful than its Milanese predecessor: at least Olgiati and company could say that they actually managed to kill their target before everything else hit the fan.

And republic or not, Sforza’s murder did shake up the polity. It put the Duchy of Milan in the hands of his wife, as the unsteady regent of a seven-year-old heir. A few years later, the late duke’s brother Ludovico displaced the regent and effectively bossed Milan until the French imprisoned him in 1500 during the Italian Wars.

While he had the run of the place, Ludovico Sforza commissioned of Leonardo da Vinci a monumental equestrian statue in memory of his brother that da Vinci never finished.† Quite strangely, the master’s notes were plumbed by a 20th century Pennsylvania airline pilot who dedicated the latter part of his life to actually casting “Leonardo’s Horse”.

* The names Visconti and Sforza are also associated with some of the earliest tarot decks and among the first to introduce to playing cards the use of trionfi, or “triumph” cards — that is, “trumps”. One can readily purchase present-day reprints of this historic pack.

** There is a positively maddening inconsistency, thus far irresolvable for this author, between accounts (here’s one example | and another) asserting that Carlo Visconti was slain by Sforza’s bodyguards directly after the assassination, and other accounts (like Gregory Lubkin’s 1994 history of Sforza’s Milan) that put Visconti on the scaffold beside Olgiati.

† Da Vinci’s ponderously slow progress on this high-profile project led Michelangelo to cattily impugn the rival artist’s bronze-casting aptitude.

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1502: Ramiro d’Orco, discarded by Cesare Borgia

Add comment December 26th, 2014 Headsman

On this date in 1502, Ramiro d’Orco (Ramiro de Lorqua or de Lorca) was put to death in the main square of the city he had governed mere days before.

In 1498, Cesare Borgia, the bastard son of Pope Alexander VI, resigned his cardinalate* to pursue a conqueror’s laurels.

Dynastically allied with France and backed by il papa‘s ducats and decrees, Cesare seized control of Romagna after Alexander helpfully pronounced his vicars there deposed.

As Borgia extended his sword up and down the peninsula, he left his Spanish steward Ramiro d’Orco in Romagna’s capital of Cesena as his governor. D’Orco was a capable, cruel ruler. But his fall likely owed as much to his master’s gifts for the condotierro racket as to d’Orco’s overeager resort to torture and public executions .

Borgia’s conquests multiplied his rivals, fellow condotierri who feared that he could soon come to dominate Italy. The discovery of one plot by former allies against him might have inspired Borgia to consider the damage that the captain of Romagna could do, should he shift his loyalties.

Borgia, not present for events, had d’Orco arrested by surprise on December 22. He was on Christmas condemned to death for graft, and by the next day’s light his black-bearded head surmounted a bloody pike. Borgia also thereby reaped the benefits of d’Orco’s brutality while also dissociating his own person from the resentment those methods had engendered.

Niccolo Machiavelli, Florentine emissary to the Borgia court, watched Cesare’s career closely. In The Prince, Machiavelli is full of skepticism for rulers who come to power through the “fortune” of inheritance or another ruler’s patronage — but Cesare Borgia rates an exception. The conqueror “laid sufficiently good foundations to his power.”

When the duke occupied the Romagna he found it under the rule of weak masters, who rather plundered their subjects than ruled them, and gave them more cause for disunion than for union, so that the country was full of robbery, quarrels, and every kind of violence; and so, wishing to bring back peace and obedience to authority, he considered it necessary to give it a good governor. Thereupon he promoted Messer Ramiro d’Orco, a swift and cruel man, to whom he gave the fullest power. This man in a short time restored peace and unity with the greatest success. Afterwards the duke considered that it was not advisable to confer such excessive authority, for he had no doubt but that he would become odious, so he set up a court of judgment in the country, under a most excellent president, wherein all cities had their advocates. And because he knew that the past severity had caused some hatred against himself, so, to clear himself in the minds of the people, and gain them entirely to himself, he desired to show that, if any cruelty had been practised, it had not originated with him, but in the natural sternness of the minister. Under this pretense he took Ramiro, and one morning caused him to be executed and left on the piazza at Cesena with the block and a bloody knife at his side. The barbarity of this spectacle caused the people to be at once satisfied and dismayed.

* In fact, he was the first cardinal ever to resign the position.

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1502: Vitellozzo Vitelli and Oliverotto da Fermo, Borgia casualties

Add comment December 31st, 2013 Headsman

On New Year’s Eve 1502, Cesare Borgia had two treacherous condottieri put to summary death at Senigallia.


The Showtime series The Borgias got canceled before it reached this particular depredation in Cesare Borgia’s career.

The “nephew” — that is, son — of Pope Alexander VI, Cesare resigned a cardinalcy in 1498 to follow his true passion, bloodshed, and set up as one of the Italian peninsula’s warring dukes. He had many a martial adventure before getting ambushed by a party of Spanish knights in 1507. Machiavelli considered him an able leader compromised by owing his temporal power to the pope’s territorial allotment. In The Prince, Machiavelli remarks on the lesson of Borgia’s reign, that “he who has not first laid his foundations may be able with great ability to lay them afterwards, but they will be laid with trouble to the architect and danger to the building” — and yet Cesare Borgia’s own fall months after his patron paterfamilias passed “was not his fault, but the extraordinary and extreme malignity of fortune.”

Cesare went from victory to victory in the first years of the sixteenth century, enough so that he threatened to make himself hegemonic in Italy. Several of his own allies, of which our day’s principals Vitellozzo Vitelli (his family ruled Citta di Castello) and Oliverotto da Fermo* (lord of Fermo) were two, began plotting against him and sent out feelers to build an anti-Borgia alliance among small powers who fretted the prospective domination of Cesare. (Though Borgia had them killed on a separate occasion, the others of note for purposes of this post are two members of the powerful Orsini family — Francesco Orsini, known as the Duke di Gravina; and, Cardinal Pagolo.)

As Florence’s own representative to Borgia’s court during the events in question, Machiavelli had a first-person view of events and recorded them in some detail. Taken on the back foot momentarily, Borgia stalled, firmed up his relations with friendly cities like Florence, and beat a brief tactical retreat. He came to terms with his friends-cum-rivals, who once more resumed campaigning on Borgia’s side.

Putatively back on the same team, several of the plotters soon found themselves at a stalemate besieging Senigallia, which refused to surrender to any but Borgia himself. They were therefore required to summon the dangerous prince from Lombardy. True to his name, Borgia did not miss the opportunity of an innocent invitation to destroy his foes.

Borgia marched into Seniallia with 10,000 infantrymen and 2,000 cavalry for a friendly little reunion. According to Machiavelli (who in this passage refers to Borgia as Duke Valentino, or simply as “the duke”),

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.

* Machiavelli also wrote up Oliverotto in The Prince.

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