Circling a Square

 Circling a Square

Class of 2017 "Doolies" in Dining Hall
During Basic Cadet Summer Training

    Recently, in The Spaghetti Western blog, I found myself reminiscing about my childhood cap-piston cowboy days as a novice “square shooter.”  The phrase seemed fitting for a kid who imagined the Wild West as a place where every problem could be solved with a six-shooter and a trusty horse. 

Years later, only days after graduation from high school, I entered a very different frontier as a newly minted Air Force freshman cadet, known affectionately or perhaps not so affectionately, as a doolie.  The term stems from the Greek word doulos, meaning “slave” or “servant” and served as a daily reminder that I’d arrived at the bottom rung of a very tall ladder.  I soon discovered another kind of square.  This time I wasn’t playing “square shooter.”  I was being taught to become a “square eater” in the Academy dining hall.

While upperclassmen ate like ordinary human beings, we had not yet earned that luxury.  We had
rules instead: a strict code governing newly arrived novitiates like me.  We followed two rules at table:

"U-Gotta-Wan-It" ... A Newly Arrived 
Doolie Meets an Upperclassman

the first was “eyes in the boat,” meaning our gaze had to remain fixed on the center of our plates throughout the meal.  As young eaglets being groomed for life in the “wild blue,” the nautical metaphor seemed misplaced.  I wondered silently why a boat had wandered into an Air Force dining hall. Of course, no one asked for my opinion.  While the Academy had many traditions, soliciting feedback from a doolie wasn’t among them. 

The second mealtime canon was even more memorable: we had to “square corners” with our forks.  Rather than lifting a fork naturally in a graceful arc from plate to mouth, we were required to move the utensil in a precise square pattern, straight up from the plate, then directly toward our waiting mouths.  Squaring corners was a ritual designed to build discipline, precision, and attention to detail.  We did it everywhere, even in hallways when an upperclassman approached.  Apparently even mashed potatoes and smacking against the wall became character-building exercises. 

By Parent’s Weekend I’d lost weight.  Whether the result of fork drills, a summer of exercise, or simply the realization that cafeteria food was now a training method rather than a meal, remains open for debate.  But the future would see this ingrained discipline and consistency rewarded in the strict, to the letter, adherence to procedure and checklists.  Time and again it saved my life.

Conversation was another matter.  At meals, you never spoke unless addressed.  Between forkfuls, answering questions became yet another exercise to endure.  I vividly recall one upper-class

To Young Me, It Was Something Called 
"The Kentucky Derby"

cadet from bluegrass Kentucky who decided to interrogate me about horses.  Unfortunately, there was little I could do to shield myself from his criticism.  He’d chosen a subject about which my expertise was roughly equivalent to my current knowledge of quantum physics.  I had no idea what the top three races were beyond a lucky guess at the Kentucky Derby at Churchill Downs.  Horses were a distant concept for a kid raised in an industrial New England town.  He may have grown up surrounded by stables.  I considered myself fortunate to have had a cat.

A Kilo of Equina Please

    Being Italian, however, I did know a little something about horses ― horsemeat (carne equina) is a popular meal choice in Italy.  Wisely, I didn’t mention this fact that I’d once heard during family mealtime where conversation was seldom calm dialogue, and only “any-which-way” strategically timed fork movements guaranteed your plate would remain filled.  Somewhere in those boisterous exchanges there was also made mention of an ancient horse race in a faraway place I was unfamiliar with.  It was an obscure reference and topically in bad taste for me to voice to someone so obviously keen on and especially during Academy mealtime interrogation.  A doolie offering unsolicited foreign historical commentary was about as welcome as a horse wandering into formation.  I’d need to wait a year or two.

Time drip-dripped and decades passed.  Eventually, Maria Elena and I, our language fluency lacking, discovered this foreign place together, extracting meaning from it in a way only first-time tourists can ― slowly, enthusiastically, and occasionally without knowing exactly what we were looking at.  In Tuscany, we eventually reached what seemed like a fairy-tale place following a brief train ride from Certaldo and our agriturismo home base, Tenuta Torciano (click).  On the

Tower-Laced Skyline of San Gimignano 

horizon stood the remaining towers of San Gimignano, rising like medieval exclamation points against the Tuscan sky.¹

Then came Siena which revealed itself slowly, almost theatrically.  The memory that remains most vivid is the great shell-shaped Piazza del Campo, where we sat on the warm brick pavement, shifting from one patch of shade to another as the slender fourteenth-century Torre del Mangia clock tower cast its moving shadow across the square.  The tower seemed less like a building than a giant sundial, quietly reminding us that, as always, time was passing.

We wandered through the Palazzo Pubblico, Siena’s

Effects of Good and Bad Government Side by
Side in the Hall of the Nine, Palazzo Pubblico

Gothic town hall, and stood before two monumental paintings, Good Government and Bad Government.  Their immense scale and historical significance left a lasting impression.  Today copies, greatly scaled down copies, hang on our walls.  Those moments remain among our treasured travel memories.  Yet whenever we think of Siena, another image comes to mind, one we have yet to experience.

Though, in my humble estimation, it is far too early to rush around checking off the final items on a “bucket list,” as a return to Siena has earned on ours.  We did not miss its

Started Mine Early

most celebrated spectacle through poor planning or chance.  We missed it for the simplest reason of all: Timing.  

This extravaganza occurs only twice each year.  And true to its rare schedule, it arrives with enormous drama and is over almost as quickly as it begins.  Its infrequency is part of its magic, drawing visitors from across the globe who compete for the simple privilege of being there.

On those occasions, Siena transforms.  The city swells to spill over capacity, like a stadium overflowing before a World Cup final.  Crowds pour into the Piazza del Campo, claiming every possible viewing position, hours, sometimes days in advance.  In the center of the square, spectators stand shoulder to shoulder inside an dirt track as the piazza becomes the stage for one of Italy’s most extraordinary traditions.  This is not a medieval reenactment staged for tourists.  It is not a flag-throwing performance, although one can precede the race, nor a nostalgic nod to another era.  This is the Palio di Siena.  

Piazza del Campo on Race Day

The Palio is a breathtaking bareback horse race and a fiercely cherished civic tradition whose origins stretch back centuries, first mentioned in a document dating to 1239.²  Piazza del Campo is not merely a beautiful square.  It is transformed into a living theater.  Siena remains one of those rare cities where communal structures still shape modern life, and the Palio is its most vivid expression — a spectacle carrying nearly eight centuries of memory, rivalry, faith, and pageantry.

The race itself has evolved significantly.  For centuries, it was run “alla lunga,” a long-distance course beginning outside the city walls and ending at the Cathedral.  The route was thrilling but dangerous as horses thundered through narrow medieval streets where stone walls and sharp turns left little room for error.²  Its deeper roots reach into medieval public games held in Piazza that included contests of strength, jousting, even bullfights.  By the 13th century, Siena was already holding horse races in honor of the Virgin Mary. 

    The first circular Palio or “alla tonda” held in the Campo in 1633, establishing the form recognized today.  But calling the Palio a sporting event only tells part of the story.  It is more accurately a civic and religious ritual. 

By 1701, the twice-yearly race had been fixed on important Marian feast days: 2 July, dedicated to the Madonna di Provenzano, and 16 August, dedicated to the Assumption of Mary.  The July race is beloved but the August steeplechase, associated with the Assumption, thought more prestigious, is exalted.  Together, they are not simply two competitions on a calendar, they are two acts of civic devotion.

At its heart, the Palio belongs not to tourists but the living heartbeat of Siena’s seventeen Contrade (districts), which extend outward from the piazza.  These are historic districts that have shaped the city’s identity since the Middle Ages.  Originally medieval military companies, the tight-knit Contrade evolved into neighborhoods, social clubs, extended families, and cultural identity anchors, each carrying generations of memories.  To Sienese citizens, the Palio goes much deeper than a horserace.  It is history made visible.  It is the sound of centuries galloping through the streets.

Each Contrada has its own church, fountain, colors,

Surrounding the Piazza - a Breakout
of Siena's 17 Contrade

animal symbol, centuries of lore, and rivalries.  Some rivalries are friendly.  Others are definitely not.  These relationships shape alliances, betrayals, and race strategy more than any horse or jockey can.  Losing is taken personally, particularly when the winner happens to be a rival Contrada.  It is nowhere near the severity of the Capulet and Montague feud in Shakespeare’s imagined Verona, but after centuries of wins and losses, outsiders can scarcely fathom the emotional toll extracted by the swings from delirious victory to agonizing defeat. 

The pieces of a winning strategy begin to jell well before the horses enter the Campo.  The winning formula takes a special sauce that blends the quality of the horse, the jockey’s tactics, alliances, rivalries, and as might be expected, money.  In fact, being first across the finish line may not be the most important consideration.  If your sworn enemy is racing, what’s wrong with making sure they lose, even at the cost of your own victory?

Then come the true heroes, the horses.  Jockeys are hired mercenaries.  Horses are treated like sacred champions, with some winning horses celebrated for decades.  You might think that every Contrada maintained its own stable to groom their future race champions.  Not so.

Horses and riders (cavalli e fantini) are assigned formally only days before the race.  In Piazza del Campo a drawing of lots occurs at a highly charged public meeting known as the la Tratta (The Assignment).  This lottery is designed to eliminate favoritism by making horse assignments intentionally uncontrollable, thus preventing a district from providing its own horse.  In the space available only ten Contrade compete in each Palio.  Seven are selected because they had not raced in that same Palio the previous year; the remaining three are drawn by lottery from the remaining eligible districts. 

A district can only hope for a horse with proven Palio experience, one that can accelerate well during the start, and is agile enough to survive the brutal turns.  However, captains do participate in preselecting and testing horses for the lottery pool.  Technically this is not “choosing your horse,” but it does allow captains to influence which horses are suitable for the pool.  Captains try to avoid a situation where one super‑horse dominates which makes the entire Palio a single-horse drama.  If the pool contains many strong horses, the lottery proves less risky.  If the pool contains several mediocre horses, strategy, jockey selection and alliances matter more.  Captains influence their preferences by advocating for or against certain horses by arguing a horse is unsafe, inexperienced, or does not fit Palio traditions (e.g., proven runners, “veterans”).

Once a horse is drawn, the Contrada’s racehorse groom and guardian, the barbaresco takes custody of the horse.  From that moment on, the horse becomes the center of the district’s life until the race.  It becomes almost sacred to the Contrada, blessed in the district’s church, and guarded day and night.  Only following assignment can the chess match of maneuvering fully play out for advantage through strategic deal-making, sometimes with a hint of scheming involved. 

Jockeys are selected by individual Contrada not for the piety they display during church services but for their cunning.  They need to dominate the famously chaotic mossa (the start), block rivals; negotiate the dangers of riding bareback on this treacherous track; and, above all, follow contrada orders, even when those orders mean sacrificing a chance to win in order to prevent a rival from doing so.

And then there is the money.  What outsiders might call cheating has been woven into the tradition.  It is no secret that Contrada negotiate covert pacts with one another:

“You help us at the start.”
      “Create traffic to block our rival.”
      “If you win, we’ll fund your feast, if you ….”
      “Support us now and we’ll support you later”

Siena does not describe this as corruption.  Instead, they prefer to elevate its characterization to “ritualized negotiation” and part of tradition.  Counter alliances and secrecy are all part of the negotiations.  It is “pay to play” morphed into “pay to win.”  It seems Sienese horse racing, having arrived centuries before John Lyly wrote in 1578 that “the rules of fair play do not apply in love and war,” had already decided that the Palio belonged in the same category.  Fair play, apparently, is negotiable. ³ 

 Then comes the mossa.  The Start of the Palio,²

Palio Start With the Rincorsa Horse Far  
to the Right Ready to Storm the Line

(click) unlike most horse racing starts, can determine as much as 70 percent of the race outcome.

§  Nine horses line up between ropes.  The tenth horse, the rincorsa, waits behind and outside the rear rope.

§  There is no mechanical starting gate as with a thoroughbred horse race.  No orderly countdown.  Instead, the rincorsa charges into the pack, triggering the start.

§  Jockeys immediately shout, shove, block, and fight for position.

§    False starts are common.

§ A perfect start can make the race unwinnable for everyone else.

The horses run three clockwise laps around the Campo on a dirt track laid over the brick piazza.  Danger is part of the tradition’s identity and like Spain’s Running of the Bulls is intentionally built in. 

Crash at the San Martino Turn

The Campo’s geometry creates sharp, uneven turns, none more notorious than the especially treacherous downhill San Martino turn back toward the tower.  Horses skid, jockey’s slam into one another, and falls are common.

Once underway, strategy becomes brutally simple:

If ahead: block aggressively, force a rival wide, use the whip strategically even against other            horses and riders.

If behind: exploit alliances, disrupt the leader’s rhythm, pray for a helping hand of someone            ahead makes a mistake or falls.

After all that buildup, the actual competition is breathtakingly brief.  The Palio may be one of Europe’s oldest, fiercest, and most theatrical of civic rituals, but it lasts all of about ninety seconds.  Centuries of tradition, months of anticipation, days of maneuvering, religious ceremonies, political alliances, money, strategy, horses, jockeys, rivalries—and then it is over before you have time to finish a cup of coffee.

It is legitimate for a riderless horse to win, for the horse is the competitor, not the jockey.  It has happened.  Most recently, in August 2023, “Crowned Goose,” representing the Oca Contrada, lost its jockey mid‑race yet crossed the finish line first, securing the victory.  Imagine spending months preparing for victory, watching your jockey

A Case Where a Riderless Horse Wins!

hit the dirt, and discovering that your horse has decided to finish the job without him.  That, in Siena, is called winning.

Victory celebrations can last all year with the winning Contrada holding feasts, parades, and rituals that can continue for months.  The triumphant district receives the pallium, a hand-painted silk banner that becomes an object of enormous pride to the Contrada.  History records that the last-place finisher received a pig.  A document from 1239 records a man being fined for refusing the pig awarded to the loser.  Even in medieval Siena, apparently, nobody wanted to be reminded of coming in last.  Today, the Contrada that comes in dead last is said to have “preso la cuffia,” literally “taken the cap.”  It’s not a prize but a mark of symbolic shame that Siena uses for social and political humiliation.  It matters because Palio rivalries are intense and deeply historical.  In the July 3, 2026 Palio, the Nicchio district “took the cuffia,” becoming not only the last place finisher but grabbed the added distinction as the “nonna del Palio.”  This distinction as “Grandmother of the Palio” marks this district as the Contrada with the longest victory drought. ⁴  True to its name Snail (Nicchio) indeed.  As I hope to have inferred by this point, Siena takes its races seriously.  

The Palio has even found its way onto the big screen.  In the 2026 romantic comedy, Solo Mio, staring Kevin James with a cameo by Andrea Bucheli, a brief scene offers a glimpse of the race from a balcony.  But Siena insists the Palio exists for Sienese identity, not entertainment for tourists.  Nonetheless, thousands descend on the city, crowding into the square or pay €1000-€1500 for the

privilege of watching from private balconies overlooking the Campo.  

Viewing from the square is free, non-ticketed, and first come, first served.  But wow, hold your horses.  Free does not mean easy.  Watching from the center of the Campo may be the most taxing way to experience the Palio: no shade, no seating, no bathrooms, and, once the crowd is packed in, no easy exit until the race is over.

But from wherever we watch it, we want to be there.  Because the Palio survives not as a reenactment of the past but as the past still being lived.  It binds neighborhoods, preserves medieval identity, turns rivalries into ritual, and compresses nearly eight centuries of memory into ninety explosive seconds. 

And perhaps that is why the story comes full circle for me.  As a child, I imagined the Wild West as a place where a horse, a six-shooter, and a little courage could solve almost anything.  At the Academy, I added “square eater,” one fork movement at a time, to “square shooter” and wondered why.  And like Daniel LaRusso, the Karate Kid endured “wax on, wax off,” I later realized it was all in preparation for what lay ahead.  Like rounding the corners of a square into a circle through continuous drill, rehearsal, and simple traditional repetition like the Palio, it becomes a part of us. 

In Beautiful Ruins by Jess Walter, I recently read:

“All we have is the story we tell.  Everything we do, every decision we make, our strength, weakness, motivation, history, and character – what we believe – none of it is real; it’s all part of the story we tell.  But here’s the thing: it’s our goddamned story!”

Unfortunately, had this been written years ago, I’d have had a story to tell that upperclassman.  One not simply adding to our rhythmic eating but one appending a wowing fourth race to the rather stodgy list of races he expected from me.  Damn the ensuing rebuff and demerits for speaking out of turn I’d have reaped.

Just maybe it’s time.  After all these years, bucket list aside, I find myself wanting to return to Siena.  Siena, where seventeen ancient rivalries, ten horses, ten jockeys, a piazza full of humanity, and centuries of Italian history merge into one magnificent ninety-second sprint on an improvised circular track inside a square piazza.  Siena, where the Palio becomes part of my goddamned story. 

See you in Siena.  

From that Rogue Tourist, 
Paolo

 

Refs:

1.  Tenuta Torciano - Wine and Tastings in San Gimignano, https://www.torciano.com/en/

2.  Race Start Video, https://www.youtube.com/watch?v=pDafJprXa90

3.  Origin of “All Is Fair in Love and War,” John Lyly novel “Euphues: The Anatomy of Wit”

4.  www.https://gazzettadisiena.it, 4 July 2026 report of 3 July 2026 race