And his company had the results to prove that the two-year-old Half Moon Bay event may soon rival the Concours d'Elegence in Pebble Beach, which many consider the premier vintage car event in all the world.
The Ritz-Carlton, Half Moon Bay squeezed in thousands of people willing to pay as much as $65 each to see more than 300 vintage and collectable motorcycles. Cars were parked all the way up Miramontes Point Road and up and down Highway 1 for at least a quarter mile in each direction.
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In its second year, Legends grew bigger, better organized and began to garner serious international attention.
The event is a combination of high-end auction and historically minded showcase for generations of meticulously restored motorcycles. It may have come along at the right time to fill a lucrative niche in the automotive world.
"The whole scene has really changed in the last 20 years," said David Reidie, a judge at the event and the owner of an Australian motorcycle dealership. "It's turned more toward the preservation of different generations of bikes and not just rebuilding. Authenticity is the catch cry."
For some of the older bikes on display, "authenticity" means "dangerous" by today's standards.
Saturday, a 1922 Excelsior "Big Bertha Hill Climber" stood quietly in the shade. But it was once ridden to victory by Edward Ryan in hell-for-leather uphill sprints. The battered but functional machine had a nasty metal outer rim clamped to its back wheel that bristled with blades like a mutant snow tire. And there were straps on the handlebars for the riders' wrists.
"Oh, man ..." said one onlooker. "Talk about being next to a lethal weapon."
Several world-speed-record Vincents from the 1940s and 50s were on display, complete with hair-raising photographs snapped as they pushed 150 mph on the Utah salt flats. The photographs gave a glimpse of motorcycling's split-second mortality.
Charley Boorman, the motorcyclist and author who completed a round-the-world motorcycle adventure with actor Ewan McGregor, had flown from London for the event.
"This is very luxurious," said Boorman. "It's a real expression of the art of motorcycling." Boorman said that as far as showcases go, Legends was quickly becoming the top event in the world. The auctioneers agreed.
"We thought we'd try 40 or 50 bikes," said Malcolm Barber, the CEO of Bonhams and Butterfields. The auction house was present last year as a sponsor - and to size up the potential for a serious sale, he said. Barber and his associates liked what they saw. Bikes were shipped in from all over the world for a main auction held at the end of the day. Bidders were on the line from Greece, Spain and Austria, Barber said.
The auction paid off. Bonhams and Butterfields recorded $800,000 in total sales. A 1914 Henderson sold for $93,600, as did a 1929 Indian.
"This was a bit of a toe in the water for us this time," said Osborne.
Osborne said top-end car collectors were starting to get involved in motorcycles as well and that a comparison to the Concours d'Elegence in Pebble Beach was in order.
"If you are offering a six-figure motorcycle, Legends has got to be the place," he added. The auction house will certainly return if invited, he said, adding that he expects the event to grow rapidly for top international collectors.
Out on the lawn some Coastside locals were getting their first taste of Legends. Ray Ebersole had a couple of bikes in the show and has been working on old motorcycles "all my life," he said.
"I think it's a great show, probably the classiest motorcycle event I've been around," said Ebersole. But the sight of so much high-end work and gleaming restorations seemed to overwhelm him a little. He has a 1927 Henderson "long tank," for which he machined some of the parts himself.
"I have a picture of a family of five riding to church on it from the lady I bought it from in a barn in Iowa," said Ebersole. "It's that history that makes it fun. That's much better than all this shiny stuff."
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