For Richard Pickering, his 1955 Triumph TR2 brings him full circle, back to the day when he was a young car nut growing up in Toronto.

At that time, those with a high percentage of gasoline coursing through their veins (leaded of course) were divided into two polarized automotive camps – the ’55 Chevy crowd and the Tea Cuppers.

Richard found himself drawn to the latter, embracing the weird, wonderful, oil dripping and oxidizing world of two seat roadsters from ‘Ol Blighty. It was quite a scene back them, with bountiful pickings from the likes of MG, Triumph, Sunbeam, Austin Healy, Jaguar et al.

This fraternity embraced the de rigor string-back driving gloves, tweed caps and even the odd fake British accent. It was all about the adoption of a lifestyle. “Most of the guys didn’t even know what handling meant.”

As with any society, it was hierarchal and certain protocols had to be observed. A Bug-Eye Sprite approaching a Triumph on the road would guarantee a friendly headlight flash and wave from both parties.

However, said lower rung cars would not flash a Jag E-Type unless he flashed first. Which he most likely wouldn’t.

Yes, the time-honoured Upstairs/Downstairs British class system made its way across the pond within the fragile doors of these tiny ragtops.

And tiny they were. Standing next to Richard’s TR2, its cowl line hovers well below the family jewels and every detail is a study is quaint delicacy. The fender mounted rear view mirrors looks as though they could snap off in your hands, and the gloriously thin-rimmed steering wheel with its fine metal spokes is a work of art. Still, after 60 years the doors close with the solid click of an antique fridge.

Since learning to drive at the tender age of thirteen in a Sunbeam Alpine, Richard has spent a life immersed in car culture, from co-hosting automotive TV shows to putting together special exhibits for the Toronto Auto Show (he’s got stories about Carol Shelby) to racing his highly modified ’68 Camaro Z28.

He now owns BHG Media Fleet services in Toronto, where on any given Monday one is guaranteed to find a posse of auto writers sitting around chewing the fat and telling lies.

After selling his Z28 a couple of years ago, Richard decided he wanted something analogue. Primitive was his word. Waving his hand toward the window, he notes “When you’ve got a parking lot full of F-Types, civilized just wasn’t going to cut it.”

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