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One Foot Wrong: An Alternate History of the Siege of Forli

By Charlie Allison

Caterina Sforza as painted by Lorenzo di Credi

In January 1500, Cesare Borgia concluded his twenty-four day siege of Caterina Sforza’s fortress of Ravaldino in Forli, Italy. Cesare Borgia sacked Ravaldino, captured Caterina Sforza and eventually imprisoned her in a Roman fortress when she refused to sign over her claims to Imola and Forli to the Papal State. The French troops under Cesare—on loan from Louis of XII France—were so impressed at Caterina’s vigor and courage during the course of the siege that they took her under their personal protection en-route to Rome, though they were powerless to directly defy their temporary employer. When she was freed after a year of hellish imprisonment from the dungeons of the Castel Sant Angelo, it was due to pressure from the French envoys. Caterina Sforza, the woman who had once held the college of cardinals under siege with artillery from the same fortress she had been imprisoned in, knew how to make an impression.

The foundational gains for Papal power in the Romagna started with Cesare Borgia’s victory over Caterina Sforza in 1500. Up until then, the Romagna, in central and north-central Italy, was only nominally part of the Papal State. In reality, the region consisted of dozens of petty lords, decentralized and quarrelsome, owing no loyalty to Rome. The siege of Forli was Cesare Borgia’s initial foray into the Romagna— bloody deeds and political dealings that Machiavelli immortalized in his works On The Art of War and most famously, The Prince. The goal was to carve out a critical foundation for increased Papal reach and control over the region at his father, the pope’s instigation. Cesare Borgia succeeded, and Forli was the first step.

The consolidation of the Romagna into the Papal State’s infrastructure and power continued until 1503 with the death of Pope Alexander VI. After that, Cesare was forever on the back-foot—losing his reputation, his finances and his political power thanks to the maneuvers of his father’s successor, Pope Julius II. He died in ignominy in Spain. Much of Pope Julius II’s power-base in the Romagna that he depended on to fight Venice, France and Ferrara had been won by Cesare Borgia. To whit: the petty lords wiped out or brought onside, its people taxed, the fortresses held firmly by the Papacy. The Romagna was the battery that made the Papal state a power from 1500 onwards.

As we shall see, this degree of power and expansion by the Papacy was only possible due to the one-time loan of French troops and wall-breaking cannons in their possession, combined with Cesare’s leadership at Forli. Had Borgia failed at Forli, especially if he'd been captured or killed, it is unlikely the Papal State would have become the force it did in the Franco-Italian wars, the War of the League of Cambrai, or even sufficiently wealthy enough to shape policy to warrant the existence of a Reformation.

And there was nothing pre-ordained about Cesare Borgia’s capture of Caterina’s fortress of Ravaldino. If not for luck, timing and a remarkable display of agility by Cesare Borgia, it is likely that we would be living in a very different world.

On Christmas Day, 1499, about a week into the siege of Forli, Caterina Sforza played a bluff. Caterina knew that the pope wanted to conquer her lands to enrich the Borgia papal dynasty—she said as much in her letters. Caterina’s own counselors had warned her about this invasion well in advance, in particular Calmeta, who wrote: “Everyone is waiting for your undoing and ruin, most of all Rome, from whence comes this evil.”

Caterina Sforza was determined not to make this an easy siege for the Borgia heir. So she employed some deception and ordered the Lion of Saint Mark—the flag of Venice—flown high over her rocca of Ravaldino. She commanded the cannons fired into the occupied town of Forli, where the Papal troops were billeted, as a distraction. She hoped to cause confusion and fear among Cesare Borgia’s ranks—and for a few hours she succeeded.

Banner of Saint Mark

Venice was a powerful wild-card player in Italian politics and had a vast network of alliances and spies strewn like landmines across the Italian peninsula. You never knew who might secretly be best-friends with Venice, therein lay the danger. Cesare Borgia recalled all his troops from their plundering and foraging. He sent scouts out to see if this bold claim of assistance was true—had Caterina Sforza been a secret ally of Venice the whole time? Had his troops just blundered into a hornets nest? Was a Venetian army marching on Forli to help her? Cesare’s rapid gains—the town propers of Imola and Forli that Caterina had once ruled—looked in danger of being undone as swiftly as they had been accomplished.

Borgia set up a perimeter for defense and waited anxiously for his scouts to return. The horsemen returned hours later bearing news—no Venetian army was coming to destroy the force sieging Forli. But during those brief hours, Caterina achieved her two goals for the day— to give the remaining citizens of Forli a few hours of peace and make Cesare Borgia look foolish and unprepared. She had wasted Cesare Borgia’s time.

Time was the most valuable thing, more valuable than food, than ammunition, even than men. The longer this siege went on, the more chances for the situation to resolve in her favor. Caterina’s sister, Bianca Maria, was married to the Holy Roman Emperor, the same Holy Roman Emperor who was hosting her uncle, Ludovico Sforza, after the French had ousted him from his throne in Milan. Ludovico had hired himself an army and was marching to retake Milan any day now—a move that would require the French to fight him—and that meant her salvation.

After all, the majority of the Borgia forces were French and on loan—they were expected to return to Milan at their king’s command, no matter Cesare’s situation. Without the French—both their numbers and their game-changing, wall-destroying cannons that were the only real threat to the fortress—the taking of Ravaldino with papal troops and assorted mercenaries was a laughable idea. The expedition to the Romagna would be over the second the French left and Cesare would have to retreat in disgrace. That or risk battle with professionally trained soldiers who were entrenched in an impenetrable fortress.

Cesare Borgia was in a precarious position: Caterina Sforza had powerful friends and family in high places, any one of whom might send her aid—the Germanic Holy Roman Empire far to the north was one, ever-cagey Florence to the west another. Both of those players had good reason to want Cesare Borgia’s enterprise to fail.

The fortress of Ravaldino at Forli

The siege was not a private affair. According to historian and pre-eminent biographer of Caterina Sforza, Elizabeth Lev, the siege of Forli was crawling with eyes from the major powers. France, Spain, the Holy Roman Empire, Venice, Rome and Florence all had their spies and informers around the town and fortress of Forli—and wrote copious correspondence as the siege unfolded.

And aside from the figurative eyes of geopolitical actors, there were garden variety gawkers and curious onlookers, those who survived the pillaging of Cesare’s troops. This was a confrontation with a very real audience—people who were curious to see the most dangerous man in Italy square off against the tigress of Forli. They wanted a show, and they got one.

It was in this very public context that Caterina Sforza parleyed with Cesare Borgia the next day, December 26th 1499: Caterina on the battlements of the castle, the pope’s son under a white flag. Cesare Borgia made his usual mix of promises, praises, and threats: if Caterina surrendered Ravaldino and came out peacefully, all would be spared. She would be safely escorted to Rome and compensated for the loss of her lands.

Caterina accepted his compliments with good grace, but then proceeded to skewer the Borgia heir. How could anyone trust a word he said—the Borgia word and its worth were known to be worthless throughout Italy. No matter his accomplishments, Caterina concluded, she simply couldn’t believe a single, solitary sentence Cesare uttered. She showed no fear, and Cesare rode off in a huff.

Cesare Borgia by an unknown painter

Several hours later though, Caterina called a second parley and tried a different tact. She lowered the drawbridge and walked out along it alone. Cesare arrived on horseback in full armor and dismounted. Caterina, according to Lev, feigned contrition and a certain degree of coquettishness. She invited Cesare to come and discuss terms inside Ravaldino. Cesare had always fancied himself a ladies’ man.

Cesare walked to the edge of the drawbridge and reached out to put one hand on Caterina’s shoulder. Caterina Sforza gestured back, suddenly demure—they could certainly talk more inside. She turned her back on Cesare Borgia and walked back along the drawbridge.

Cesare stepped onto the drawbridge. One boot then another. Two steps now. On the third step, Cesare felt the bridge move under him.

The drawbridge was being pulled up as he stood—dumping him towards the fortress. He turned, realising with growing horror the obvious trap he’d been lured into—and jumped for the safety of solid ground. In our timeline, our history, he made the leap to safety—but in this one, Cesare Borgia fails. The bridge went up, he lost his footing and the pope’s son’s fate was sealed. Cesare Borgia was trapped like a cockroach under an upside-down cup.

Cesare Borgia wouldn’t get to bombard Ravaldino for ten days with the latest French artillery when it arrived, crumbling the up-to-now invulnerable walls to powder as he does in our timeline. He wouldn’t even get to dig under the moat of the fortress or offer a thousand ducats for Caterina’s head. He wouldn’t be able to take the meager plunder inside the fortress or capture and rape Caterina Sforza as he did after the end of the siege of Ravaldino before shipping her to Rome, confident that he had established a crucial foothold in the Romagna.

No, Cesare Borgia’s fate—and that of the Papal State and the presumptive Borgia dynasty, takes a grim turn when he put a foot wrong on that Forli drawbridge. Cesare Borgia is a dead man. If he fell into the moat while wearing, as some sources suggest, full plate armor, he would have drowned. Or, if he lands on the banks of the fortress alive and unharmed, his situation would be no better. Perhaps one of the many archers, crossbowmen or arquebusiers on the walls of Ravaldino picks him off before he can gather his wits.

Even worse, he could be taken alive by Caterina Sforza, a woman notorious for her audacity, creativity and vengeful nature. The same woman, who when her lover was assassinated, had everyone involved in the plot and their immediate families down to the children, messily executed.

This the woman whom Cesare Borgia had threatened, repeatedly and publicly. His fate would not be pleasant. Given that in our timeline, Caterina Sforza offered a ten thousand ducat bounty for Cesare Borgia dead, we can safely conclude that the captured the Borgia heir would face immediate execution.

Even worse, at this time Cesare hadn’t yet paid his mercenaries: his capture and execution would likely spark a wave of desertions from his forces. If Caterina Sforza continued according to form, she might have simply paid them to go away. That’s the trouble with mercenaries.

Having lost their leader, the French troops—with their heavy cannon still days behind—would likely have gone north to Milan to rejoin their king early, abandoning their nominal commander to Caterina’s attentions. This Italian adventure lost its savor beneath the walls of Ravaldino.

Let us examine the immediate probable fallout from the failed expedition to Forli from three perspectives: from the local level, the international level, and the spiritual/economic level. The papal military ambitions—boosted by France before their return to northern Italy—have been thoroughly scuppered. The Borgia papacy wouldn’t get another chance to invade the Romagna with French support any time soon—that critical window had now been slammed shut on their fingers.

1. Florence acquires Forli

It is likely that Forli would fall under the protection of one of the other Italian principalities after a decisive blow like this to the papal interests. Florence is the best bet. Caterina and her youngest son, Lodovico d’Medici (the boy who would grow up to be Giovanni della Bande Neri, a legendary condottiere captain in his own right), were Florentine citizens thanks to her brief marriage to Giovanni d’Medici. Increased Florentine clout in the Romagna would be a likely outcome of this situation. Florence had been dissuaded from aiding Caterina during the siege itself for fear of a papal reprisal campaigned aimed at Pisa, a city they wanted to keep in their orbit. With the papal forces in disarray and France confined to the north of Italy, it would be more shocking if Florence didn’t use the chaos to expand their sphere of influence further still to include Forli.

Italy during this time period. Forli is considerably closer to Florence than Rome.

2. Rome is more vulnerable—to just about everyone.

The larger historical consequences of the failed Borgia attempt at securing the cornerstone of the Romagna would stretch beyond the scorched fields of Forli. There is no certainty that Rome wouldn’t be sacked well before it was historically—1527, by the Holy Roman Empire. One of the great powers—likely France—might seize the opportunity to fall on Rome earlier, and enlist the help of the various Romagnol lords—Caterina Sorza possibly included—for support.

This was an age of treachery and opportunism. Rome now lacked even the thin promise of a consolidated Romagna to repel invasion. There was no richer target in all Italy than Rome at this time. The French had proved (twice!) that they could more or less reach Rome with impunity in the opening years of the Franco-Italian wars—once on their march to plunder Naples in 1494, and again on the return trip under Charles the Affable. And without even the fig-leaf of a compliant Romagna, or hope of putting off the French or Spanish (who now controlled Naples—basically the entire southern half of Italy), the papacy’s future looked grim indeed.

3. Rome loses the Papacy

Rome might be finally played out as the holy city of Christianity after the disaster at Forli. It would be a desirable coup for Louis XII of France to restore the Papacy to Avignon and plunder Rome. Of course, the prospect of returning the papacy to French control had its share of supporters inside the college of cardinals, who would likely aid Louis or any other French conqueror in their ambitions.

Of course, Rodrigo Borgia (Pope Alexander VI) wouldn’t take this lying down—presuming France acted immediately after their capture of both Ludovico Sforza and Milan in April 1500 at the Battle of Novara. He would likely would have to appeal to Spain for help.

Even if Spain defended Rome against a French assault on the Holy See—there was no impediment to Spain doing what France had intended in the first place. To whit: either incorporating Rome into its Neapolitan holdings or simply disposing with pretense and moving the papacy to the Iberian Peninsula.

Best case scenario, the Italians accept the movement of the papacy away from the peninsula as the way things are. Worst case, the Catholic church splinters again between pope and anti-popes as it did with the first Avignon papacy.

Either the French or Spanish empire would be happy to have a king-legitimizing papacy in-house, ready to rubber-stamp policy and rulers alike. The papacy itself would grow in power, but Rome would lose its luster as a holy city. The Church as an institution would become more overtly French or Spanish, and far less Italian, politically speaking. Likely result—a newly empowered French or Spanish empire absorbs the legitimacy of the papacy, and possibly another schism in Catholicism.

4. Even if Rome is not sacked early, it is still diminished

Even if, for the sake of argument, Rome avoids a premature sacking by one of the great powers in the early 1500s, the scars made by the fiasco at Forli would likely be deep. The great legacy of the Borgia papacy—a Romagna and all its resources firmly under the Papal boot—wouldn’t exist. And neither do the funds such a state would produce.

The first popes of the 1500s—Julius, Leo, Clement—would be poorer, weaker and more at the mercy of the many foreign powers trampling over Italy—France, Spain, the Holy Roman Empire etc. This means that they cannot enact the policies for which they are most infamous. Chief among them being the ramping up of selling indulgences. With the Church’s reach and temporal power shriveled without the combined coffers of the lords of the Romagnol, few would be interested in purchasing indulgences due to the smaller pool of rich nobles. A lot of effort for little financial gain.

This makes it very, very unlikely that the Protestant Reformation occurs in the same way it does in our time-line if Rome remains the seat of the papacy. Even if the church retained Rome and the papal miter, the papacy would not be as powerful. Nor would it be as keen to push indulgences—a key issue that stimulated Luther’s criticisms and subsequent fracturing of the church into Protestant and Catholic spheres. No Diet of Wurms, no Calvinism, or Thirty Years War, for example—at least, they would be unlikely to happen in the same way, for the same panoply of reasons.

This is a lot to extrapolate from a simple failure of agility on one cold December day. The fact is that Cesare Borgia expiring or being made politically irrelevant in the last days of 1499, rather than dying in disgrace in Spain in 1507 as a broken man, changes the entire Renaissance political and geographic landscape. In his place rises Caterina Sforza, already famous for her deeds before the siege of Forli, eclipsing him and going on to shape the face of European history.

Could the Prince become the Princess?

It is not inconceivable that Cesare Borgia would be relegated to the role that Caterina Sforza occupies in our current history: a formidable historical figure whose fortunes were abruptly cut short. After all, Machiavelli idolized the Borgia heir—and despite his personal dislike for Caterina Sforza, the Florentine diplomat admitted to admiring her courage. Caterina and Cesare shared many traits that Machiavelli praised in his most famous work: unscrupulousness, political acumen, physical bravery and ceaseless ambition. In short, it wouldn’t be beyond the pale to speculate that Machiavelli might write The Prince (or an equivalent)—but with a focus on Caterina Sforza’s exploits rather than Cesare Borgia’s.

Perhaps instead of the bittersweet tune in her honor that was composed in our timeline, the people of Forli and the Romagna would sing a different story of the tigress of Forli. A happier song, for Caterina Sforza. Sadly, we must make due with the songs we have, so we will end this essay with the words of Marsilio Compagnon’s “The Lament of Caterina Sforza”, a popular song after the fall of Forli: “Ah, you frightened Italians

I will stand with my armor

I’d rather lose in battle

and die with honor

Before I’d be sent to wander

with my children through the world

and sink shamefully into oblivion,

I’d sooner be tortured and killed

Listen to this brokenhearted plea

I am Caterina of Forli.”


Charlie Allison is a writer, speaker and researcher who talks about history on his blog (where he has started a new series about Catherine Sforsa) and has had several short stories published


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