The clocks had already struck the chimes of four on a glorious day of spring, and the Mille Miglia, the greatest of all open-road events in history, was coming to an end. Quite literally. The date was May 12, 1957, and in Brescia, the start and end point of the competition in the foothills of the Italian Alps, Piero Taruffi, Italy’s senior statesman of racing, was already being celebrated for finally mastering a challenge that had eluded him twelve times before. Count Wolfgang Berghe von Trips in the second works Ferrari 315 S had followed closely behind Taruffi for a perfect photo at the finishing line, while Olivier Gendebien completed Ferrari’s perfect 1-2-3 bringing home the gorgeous 250 GT LWB Scaglietti. In fourth, Alfonso de Portago was reported to be no more than ten minutes behind, eating up the long straights separating Goito from Brescia at blinding speed. Then there was a rustling, the sort of chill that announces a tragedy, followed by the quiet, apprehensive hum of a rumor that no one, really, wishes to spread. There was talk of an accident, not a mere retirement, a serious crash, a burst tire, a blazing bullet spinning out of control, the ditch, the railing, the crowd—oh, the crowd—and the resulting scene, precisely the sort of calamity the authorities had feared so badly they had tried to stop the race from taking place in the first place.
The Mille Miglia was a thousand-mile-long road race around the northern half of the Italian boot which took competitors from Brescia to Rome and back up to Brescia in a loop that encompassed both coastlines and part of the tough Apennine landscape in the middle of the country. Inaugurated in 1927, it quickly became a crowd favorite, not least for the bravado that characterized racing in the 1930s, the days of Rudolf Caracciola, Tazio Nuvolari and Achille Varzi among many others. Suspended by Mussolini in the advent of the Second World War, the Mille Miglia came back with increased interest in 1947, and soon became the battlefield where Italy’s most remarkable carmakers—Ferrari, Alfa Romeo, Maserati, Lancia—settled the all-important question of bragging rights.
Alfa Romeo dominated the first decade of the Mille Miglia, and while Ferrari’s record after the war was impressive, with consecutive victories from 1948 to 1953, Mercedes-Benz became the only foreign marque to win the race proper both in 1931 and 1955. Ironically, 1955 was a key year for sports car racing altogether, for the horrendous accident at Le Mans, the deadliest crash in racing history, inevitably raised major concerns about crowd safety, putting the onus on the authorities and organizers, and forever changing the nature of the sport. This change, however, was gradual, and the figure of Alfonso de Portago, Fon to his friends, was right in the middle of the transition period.
Young, good looking, fearless and laid back, de Portago broke into the European racing scene in 1954 at the age of 25, after participating with Luigi Chinetti in the Carrera Panamericana the year before. Sporting a black leather jacket in the age of suit-an-tie racers, de Portago played the Jimmy Dean role for a jet-set crowd not terribly used to welcoming into their club members from Spain, perhaps the continent’s poorest and most isolated country at the time. The son of an American millionaire, Olga Leighton, and Antonio Cabeza de Vaca, a Spanish aristocrat and fierce supporter of General Franco in the Spanish Civil War, Alfonso was born in London and raised in France. Remarkably talented at sports and addicted to danger, he learned to fly as a teenager, was a three-time steeplechase amateur champion, took part in two Grand Nationals in Aintree, and eventually became attached to bobsleighing, introducing the sport in Spain and earning a fourth place in the 1956 Winter Olympics.
Fon lived life like there was no tomorrow, seizing the day like few others. Legend has it that he flew a plane under London Bridge at the age of 17, just for kicks, and by the time he was 21 he had married American socialite Carroll McDaniel, with whom he would have two children. Ever the playboy, he separated (but never divorced) McDaniel and in 1954 began dating Dorian Leigh, perhaps the first super model ever. By then de Portago had already been stung by the car bug and was acquiring quite a reputation for his uncompromising driving style. In 1955 he joined the Ferrari works team, bringing home his 750 Monza in second place both at the Venezuelan Grand Prix and, a few weeks later, at the Governor’s Cup in Nassau. After competing in the Winter Olympics in January 1956 he rejoined Ferrari, coming third in the 1000 kilometers of Nürburgring before winning the Portuguese Grand Prix in Oporto and the Tour de France for cars in a Ferrari 250GT with his good friend Ed Nelson as copilot.
Then came 1957, and de Portago’s journey through the first few months of the year could stand as an exemplary narrative of what life as a gentleman driver was all about in the so-called golden age of motor racing. Entangled in a passionate new relationship with the Mexican movie star Linda Christian, Fon came fifth in the Argentine Grand Prix, third in the 1000km of Buenos Aires and third again in the Cuban Grand Prix early in the season, before heading on a break to St. Moritz in the Swiss Alps to compete in the bobsleigh World Championship, where he would earn a silver medal. Back in the driver’s seat de Portago’s role at Ferrari would become more prominent as Italian driver Eugenio Castellotti, Enzo Ferrari’s favorite, was killed testing the new car for the upcoming season. After winning the Coupe USA in April, de Portago was included in the line up of five pilots representing Ferrari at the Mille Miglia.
The Spaniard had taken part in the competition twice before but he was not a fan of a race he considered too dangerous. Luigi Musso, another talented Italian driver, might have taken Castellotti’s place but he fell out of the fold through illness, and so it was left to de Portago to join Taruffi, Peter Collins, von Trips and Gendebien representing Ferrari on home turf in a race of utmost importance for Enzo, especially given how disappointing the 1956 season had been. Fon’s 315 S was given the green flag in Brescia shortly after 5 am, and de Portago raced a tough race, as was his wont, steadily sitting in fourth place as he went through control stations in Pescara, Rome and Florence. But in the final stop of the race, in Bologna, a mechanic noticed a bent control arm on the left side of the car, where Fon had hit a kerb and bent the wheel. Before the necessary changes could be made de Portago, urged by Enzo Ferrari himself, waved his mechanics away. His next move has been carved in racing lore forever: after a brief spell he stopped near the railings where he spotted his beloved Linda Christian, who scampered onto the track to send her lover on his way with a kiss.
The stills of that moment, dubbed the “Kiss of Death” by the world press, became the most famous photograph of 1957, for less than a hundred miles later, near the town of Guidizzolo, the Ferrari’s front left Engelbert tyre would explode, sending de Portago and copilot Ed Nelson flying at 150 miles an hour. The car hit a milestone and flew out of control over a ditch on the left side of the crowded road. By the time it came to a full halt the Ferrari had hit thirty people, injuring eighteen and killing nine, five children among them, as well as the two occupants. It was almost a suitably epic end for a man who knew not how to do things by halves—but it was also a terribly sad one.
Until the 1950s racing had always been accepted as a dangerous sport both for participants and spectators, but as cars grew faster and accidents more deadly the attitude towards the sport shifted dramatically. Even before de Portago’s end, there had been calls to stop the Mille Miglia from taking place, as it had claimed the lives of six people in 1956. The tragedy of Guidizzolo was immediately recognized as the final nail in the Mille Miglia’s coffin but with hindsight it’s obvious it didn’t simply signal the end of that race, it also marked the beginning of the end of an entire era, perhaps even of a lifestyle. Gentlemen drivers would soon give way to professionals, many of them mechanics with far greater knowledge of the machines beneath them, who would lead the sport in a very different direction. The days of the intriguing, impeccably educated, extravagant playboys competing in daredevil fashion in the most uncanny of settings—the Targa Florio around Sicily, the Carrera Panamericana in Mexico, even the rally, later on, from Liege to Rome and back again—were counted, and perhaps it was for the best. After all, looking back, those times predating political correctness seem so outrageous, so preposterous, and yet, at the same time, so bloody wonderful.
Written together with Adrian Kobbe and published by the WEEKender supplement of Sint Maarten’s The Daily Herald newspaper on Saturday May 6, 2017.