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Like many enthusiasts, I mourned the passing of sports car builder Carroll Shelby this month. But I also mourned for the greatest kiboshed car deal of all time, and for my lost chance at connecting with a legend.

It began on a summer day in 1969, when I did my daily perusal of the Ottawa Citizen's Cars For Sale section. There, wedged in with the ads for high-mileage Ramblers. clapped-out Dodges and ho-hum family sedans, were three lines that stopped me in my tracks: "For sale – 1967 Shelby 427 S/C Cobra, royal blue, 2,500 miles. Never crashed. $6,000 or best offer."

I ran to my father, who was setting up the sprinkler in the back yard. My hands shook as I showed him the ad, which I had circled with blue pen. My father gave it a quick scan, then handed back the paper.

"Don't need it," he announced. And with that, he returned to the sprinkler.

I pleaded with my father for days, but I was wasting my breath. He wouldn't go to see the Cobra. And he wouldn't lend me the money to buy it. As far as he was concerned, our Ford Falcon wagon filled our automotive needs. He had three kids to feed, and a wife who wanted a new sofa. He had no intention of dropping $6,000 on a two-seat car with no roof and a trunk that would barely hold a suitcase.

For a teenage boy in the 1960s, the Shelby 427 Cobra was the holy grail of automotive cool. And so was the man behind it. Carroll Shelby was a chicken farmer and self-taught engineer who took on Ferrari (and won) with cars he built in a concrete building out in California. Shelby had the mojo, and when you bought one of his cars, his DNA came with it.

It's hard to convey just how cool a Shelby 427 S/C Cobra was back in the late 1960s. It ruled the world of performance driving in the same way that Jimi Hendrix dominated the world of electric guitar. The Cobra was like a steroid-abusing MGB – a two-seat roadster with a stonking V-8 engine under the hood, bellowing side pipes, and steamroller tires jammed into cartoonish fender wells. It was a legend.

And now an S/C Cobra could be mine. All I needed was $6,000. But it may as well have been a million (I earned about $20 a week from my paper route). I went to the bank where I kept my savings account (balance approximately $50) and asked about a $6,000 loan. They said sure – if my parents would put up their house as collateral and act as guarantors. (My father considered my proposition for about three seconds before turning me down.)

Two days later, I called the number in the Cobra ad and asked if it was still for sale. It was. I asked the seller if he'd take any less. He said to come over with cash and make an offer. I went back to my dad. The answer was still no. A week later, the ad disappeared from the classifieds. I called the seller. The Cobra was gone. And so was my chance at owning a piece of the Shelby legend.

If I'd bought that car, I could be a wealthy man today. (Original Cobras now sell for more than a million.) But I'd probably be dead – in the hands of an untutored, speed-crazed teenage boy, a Cobra might as well have been a nuclear grenade with no safety pin.

Oh, well.

My Cobra dream was one of many that I chased and missed. But I have always felt a bond with the Cobra, and with Carroll Shelby. He and his car represented the best of America: raw energy, pragmatic yet inspired engineering, and pure, rawboned style.

The Cobra has always been out there, circling in my imagination, calling to me. The value of a Cobra has soared beyond my reach, and yet there have been unexpected connections. In the late 1970s, I got to drive a 427 Cobra that showed up at the shop where I worked as a mechanic (an awesome experience, but I realized that my dad was right – I would have killed myself if I'd owned a Cobra as a teenager).

And in 2009, I had the pleasure of meeting Peter Brock, who worked with Shelby back in the 1960s (he was Shelby's first employee). Like Shelby, Brock is a gearhead's gearhead, and a man I'd always admired. Brock helped design the original Corvette Sting Ray at General Motors, ran a car racing team, and launched a hang gliding manufacturing company that revolutionized the sport. He's an awesome guy.

I called Brock this week to talk to him about his years working with Shelby back in the early 1960s. He described an amazing time. Shelby ran his company out of an industrial building in Marina Del Rey. He had the best engineers, builders and drivers in the business – men like Ken Miles, Phil Remington, Bob Bondurant, Dan Gurney and Brock. They tested prototypes on a nearby boulevard, drifting through the long curves at more than 100 mph.

The shop was a crucible of automotive creation: sparks flew, and the space reverberated with the sound of howling engines and metal being hammered into shapes that would go down in history.

"There was a lot of energy and excitement to do things," Brock said. "It was incredible."

Brock's job was to design a car called the Daytona Coupe – a car that would win some of the biggest races in the world, including the 24 Hours of Le Mans. Brock sketched the Daytona on paper, then built plywood templates that were used to shape the aluminum body panels. The finished car was sensational, and slayed the competition.

Shelby's shop was in endless transition, with countless projects on the go. Shelby himself was like a pre-digital, gasoline-powered Steve Jobs, with instinctive taste and relentless energy. (The name of the Cobra came to him in a dream, and his engineering was pure seat-of-the-pants.) Working with him wasn't always easy. After Brock finished the Daytona Coupe, a friend of Shelby's who happened to be an aircraft designer, looked at the car and said it was all wrong, and that it needed a longer tail, like the one on the Porsche 917.

Brock had considered that option and rejected it in favour of a chopped-off version known as a Kamm tail. He knew his choice was best, and his design had been proven on the track with a long string of wins. Yet Shelby never fully accepted Brock's design.

"He could be quirky," said Brock. "But I've accepted that. The man was a legend."

Shelby's drive was reflected in both his cars and his lifestyle. He went flat-out through the decades, rising from Texas chicken farmer to world-beating car designer and racing icon. By the time of his death this month at the age of 89, he had gone through seven wives, two livers and two hearts (his second heart was transplanted from a Las Vegas gambler). In 1960, he drove a 200-mile race with nitroglycerin pills under his tongue in case his heart stopped.

Peter Brock went through some hard times with Shelby over design rights to the Daytona Coupe after he tried marketing an improved reproduction car known as the Brock Coupe. (Legal battles with the inventor of the Cobra weren't a unique occurrence; Shelby fought dozens of legal battles with kit-car manufacturers who cloned his iconic car.)

Despite all that, Brock's memory of Shelby is a positive one: "There were some tough business things that went down," he said this week. "But the guy created a legacy. I cherish the days I worked there. It was the best."

I've thought of Carroll Shelby countless times, and of that 1969 advertisement that could have connected me with him through that blue Cobra 427 S/C. It could have made me a millionaire. Or it could have killed me. But the Cobra and I were ships in the night. Probably for the best.

Godspeed, Carroll Shelby.

Click here for our special photo gallery: In pictures: Remembering automotive legend Carroll Shelby

And for more on Caroll Shelby: Like the Cobra he created, Carroll Shelby was a classic

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Twitter: Peter Cheney@cheneydrive

E-mail: pcheney@globeandmail.com

Globe and Mail Road Rush archive: https://www.theglobeandmail.com/globe-drive/car-life/cheney/

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