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Bloody Conspiracies at Castello del Trebbio


The medieval Castello del Trebbio was built in the 12th century.

By Uma Raja


A violent conspiracy. A stabbing in a church. Shady deals with the pope himself. At Castello del Trebbio, many would not expect a bloody history. The castle is located in the rolling green hills of Tuscany, burrowed in the Chianti Rufina region.


Chianti is known for producing artisan wine that is famous throughout the globe. A wine tour with Tuscan Trails allows guests to visit the winery at Castello del Trebbio. While sampling Chianti wine and nibbling on cheese and bread, guests are transported back to an era of warfare and political intrigue. What makes the tour stand out is not just delicious wine, but the comprehensive history that tour guide Todd Bolton provides.



The Tuscan Trails tour allows guests to sip on four varieties of wine at Castello del Trebbio. Vegetarian food options are available upon request.

A Sinister Past


In the 1400s, the wealthy Medici family was a household name. They sponsored the creation of timeless artworks and exerted political influence over multiple regions in Italy. The Pazzi family wanted to usurp the Medici, and it was in the Castello del Trebbio itself that the conspiracy was hatched.


Lorenzo Medici and his younger brother Juliano Medici were to be assassinated. They would have to be killed at the same time to avoid the wrath of a surviving brother. Pope Sixtus IV agreed to the plan, angered that the Medici family was pushing against papal rule in Romagna, a region in north-central Italy. If the brothers were to be killed, the pope would send in troops to ensure that the Pazzi take power.


It was almost impossible to find the Medici brothers at the same time and place. However, on April 26 of 1478, the plot would have an opening—an assassination during Easter mass in Florence’s Santa Maria del Fiore Cathedral. However, Juliano decided not to attend mass at the last minute. A few Pazzi brothers persuaded him to come, guiding him to the entrance of the church while Lorenzo stood by the high altar.


“The brothers were almost a football field length apart from each other,” Bolton said.


The signal to kill the brothers was the beginning of mass, after a bishop raised his hand to silence the church. Two trained soldiers flanked Juliano, stabbing him 19 times. Simultaneously, a priest and his assistant tried to kill Lorenzo at the altar by driving a dagger into the back of his neck, intending to sever his spinal column.


However, the priest made a large mistake: touching Lorenzo’s shoulder.


“Back in the day, people didn't touch Europe's noble families. They were constantly targets of assassination from their own siblings and cousins,” Bolton said. “Lorenzo's first reaction is to draw his sword, turning in that direction. As the priest’s dagger is coming down, the priest still gets him with a fairly nasty wound on his cheek and his neck. But because Lorenzo is turning and repositioning, it's not a lethal blow.”


Lorenzo briefly attempted to fight back and escaped by locking himself into the priest’s changing room until his forces arrive. While the younger brother died, the elder was filled with rage.


Pope Sixtus IV did not send in any troops. A major war could’ve been waged with Lorenzo still alive.


In his revenge, Lorenzo killed almost every male family member of the Pazzi family. He chose to exile the Pazzi male who was married to his sister. He also chose to slaughter any real or suspected enemies. People were rounded up to be tortured and killed. According to Bolton, historians estimate that over 350 people were killed because of the counter conspiracy.


Tour guide Todd Bolton (right) moved to Italy in 2002. Bolton earned the title of Sommelier from the Associazione Italiana Sommeliers in 2005.

“I hate when people romanticize about the past,” Bolton said. “We look at Florence and see all this beautiful art and architecture and think they were so great back then, so advanced. But it was a horrible, dirty, brutal, violent time in history. People were not just being killed. They were being eviscerated by their own entrails and hung outside buildings with their heads on spikes.”


After his rampage, Lorenzo Medici consolidated so much power that he had virtually no enemies until his deathbed. He had essentially wiped out the Pazzi, and he confiscated their wealth and property. The Medici family now owned Castello del Trebbio, the very building where the plot to overthrow them was conceived a week and half before the Easter mass.


Lorenzo knew he had to rebuild the Medici family’s relationship with the pope. He had figured out that the pope was conspiring against him, and Pope Sixtus IV excommunicated the entire city of Florence. Florentines were removed from the church until they handed over Lorenzo, which the citizens opted not to do.


Lorenzo knew the pope would either die or be removed from office. He chose to simply outlive Pope Sixtus IV and work on nestling the Medici family into the church’s hierarchy. He gifted most of the Pazzi family’s wealth and property to different districts of the Catholic church, fostering new relationships. Four popes later, Pope Leo X, would be Lorenzo’s youngest son.

Lorenzo Medici's nephew would become Pope Clemente VII.

Lorenzo would go on to sponsor artists such as Michelangelo and Leonardo da Vinci. He played a long-term game that ensured the prosperity of his family.


Castello del Trebbio Today


Castello del Trebbio was one of the properties distributed to the church. Until 1968, an administer lived within the castle and rented out the land to sharecroppers. The Baj Macario family then bought the castle, using it to produce wine and extra virgin olive oil.


Castello del Trebbio is now a site for fairytale weddings, tourist tours and a background for Instagram-worthy selfies. Flowers bloom and birds chirp as wine drunk guests stroll the property with lopsided smiles.


“Chianti is special, it’s admired and known all over the world. It offers both spectacular landscapes and spectacular wines,” Florence resident Filippo Vecchio said.


Chianti has been recognized as a wine-region since 13th century.

Tuscan Trails could have easily had guests sip on a few glasses of wine and mosey around the premises. Many may have felt content with a surface-level encounter. However, a tour of Castello del Trebbio provides an educational experience.


Guests will leave the tour with an appreciation for the meticulous work that goes into the production of wine and olive oil, and above all, a newfound perspective on the brutal reality of history. Only the select few who visit will know that the picturesque castle on the hillside hosts a dark and bloodstained history.



 
 
 

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This blog is provided by students enrolled in travel reporting within the
University of Florida College of Journalism and Communications'
2023 study abroad in Florence, Italy.

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