It was built to be a grand touring car in the true sense of the word. Fast but very civilised, the way they designed the Alfa in its day. Seventy years later we were driving one of the most comfortable cars in the entire event!

It was positively electric. When Jon and Mary Shirley’s 1938 Alfa Romeo Berlinetta won its European Classic Closed Class J-3 at the 2008 Pebble Beach Concours d’Elegance in August, along with Most Elegant Closed Car and Pebble Tour’s Elegance in Motion trophies, expectancy shot through the event’s multitudes like a bolt of Italian lightning striking coastal California.

Jon Shirley, the soft-spoken former president of Microsoft, at that moment was feeling what he’s always thought since he first brought a car to Pebble Beach in 1994 (the third-in-class Ferrari 275GTS/4 NART Spider that he and his wife Mary had prepared).

‘Best of Show is kind of a crap shoot,’ he says. ‘You can come here with a really sensational car, then somebody else shows up with something fantastic, over-the-top, and takes it.’ This from the man who’s often won his class here, but never Pebble’s big one.

An hour-and-a-half later, juried from Pebble’s 24 class winners, three top-honour nominee cars were summoned to park near the awards ramp: Sam and Emily Mann’s black Hispano-Suiza, Jack and Helen Nethercutt’s red Packard LeBaron Sport Phaeton, and the Shirleys’ dark blue Alfa Romeo 8C-2900B coupé.

Edward Herrmann, the show’s master of ceremonies for the past ten years, announced: ‘Here is Sandra KaskyButton, chairman of the Pebble Beach Concours d’Elegance, with the information we
have been awaiting!’

At 5.05pm on that overcast Sunday by the flat Pacific, the car kingdom drama peaked in front of the stately Lodge at Pebble Beach. The Alfa won. Inside the 2.9’s tan leather cabin, Mary Shirley, in pre-war couture and holding the couple’s Coton de Tuléar puppy ‘Alfa’ for ‘just a bit of extra good luck’, sat beside her husband as he drove their winning car through the confetti storm and onto the awards ramp to accept the most coveted prize in our car hobby world – Pebble Beach Best of Show.

This 70-year-old automobile later prompted Pebble’s chief judge Ed Gilbertson to tell me: ‘The Alfa Romeo 8C-2900B that won Best of Show represents all of those things we seek in selecting the top car at Pebble Beach. In addition to meeting the elegance criteria – purity in the design, styling and presentation of an object – it is a very authentic and correctly restored car that serves as an accurate barometer of a great period in automotive history.’ In a nutshell, the judges’ choice was a landslide.

For Alfa chassis number 412035, the road to Pebble Beach began in earnest right after the 2007 Concours d’Elegance when it was driven to Dennison International’s workshop in Puyallup, Washington, near Tacoma, to begin its frame-up restoration.

Jon had purchased the 2.9 Alfa coupé from David Cohen in 2005. Well exercised since
its 1983 restoration in England by Tony Merrick, the car had been driven a great number of miles by Cohen. Jon Shirley and Butch Dennison, Jon’s vintage racing mechanic and resto chief, took the Alfa to the 2006 Mille Miglia Storica. Having already done the Mille with his son Peter three times in Ferraris – 375MM, 290MM, 166MM – the long-wheelbase Alfa, comparatively, was a heavenly ride.

‘It was built to be a grand touring car in the true sense of the word,’ says Jon. ‘Fast but very civilised, the way they designed the Alfa in its day. Seventy years later we were driving one of the most
comfortable cars in the entire event!’ Says Butch about Jon’s and his 1000-mile fling through Italy: ‘We had zero problems, except for fouling some plugs going into Rome after cruising at 110mph on the autostrada.’ Butch Dennison, a hefty man of easy demeanour with many formative years as an Indycar mechanic, enjoyed a particular Mille treat crossing the Futa Pass.

‘I was driving the Alfa at the time, winding through the hillsides, and the kids up there on their motorcycles were two or three feet off our fenders – on each side of us! They trusted us, and Jon and I trusted them. It was as good as it gets.’ Jon had already done the 2005 Alfa 8C Tour out of Jackson Hole, Wyoming – steep elevation changes, lots of miles – so the Mille was cake.

Shirley’s 2.9 wasn’t always strictly a road car. During its earlier history, the Alfa at one point was owned by Frank Griswold, who entered it in New York’s first Watkins Glen Grand Prix on October 2, 1948. An eclectic group of drivers that included cartoonist Charles Addams and yachtsman Briggs Cunningham, as well as brothers Sam and Miles Collier, roared off through the town’s streets and onto outlying country lanes, 6.6 miles of cement, macadam, oiled gravel, even dirt, over a stone bridge at the top of the course and, twice each lap, traversed railroad tracks during what’s known as The Day They Stopped The Trains.

Minus the rear fender skirts and spun aluminium wheel disc covers worn now, and with its race number 35 slopped on by paint brush, the Alfa coupé prevailed over a quite competitive field of 15 open and closed cars to win the Watkins Glen inaugural, instating both car and Griswold in the pantheon of American road racing – major provenance that was taken into account 60 years later at Pebble Beach.
Trekking back to the car’s Milano birth, Alfa guru Simon Moore found that this classic 2.9 Berlinetta by Carrozzeria Touring had a certificate of origin dated July 18, 1938. In Mussolini’s Italy, the eight-cylinder 180bhp twin-supercharged bella machina was a jewel for the world to see, and magazine ads teased a hard-pressed pre-war public with its dreamy elegance.