After Larry Ellison finally took possession of the America’s Cup in 2010, he had grand plans for the race. He would transform this elite, gentleman’s sport into a TV spectacle for the masses: Nascar on San Francisco Bay. Ellison was going to reinvent the cup for “the Facebook generation, not the Flintstones generation.” Yes, disruptive innovation was coming to sailing!

In a way, Ellison has been true to his word. The result is the sports equivalent of Apple’s Newton or Microsoft’s Bob: a disruptive, innovative, colossal failure.

The America’s Cup, which likes to describe itself as “the oldest trophy in international sport,” dates to an 1851 race around the Isle of Wight in which an American schooner beat 15 members of England’s Royal Yacht Squadron. The winning crew donated the trophy to the New York Yacht Club, under the condition that it be held in trust as a challenge trophy to “promote friendly competition among nations.”

I’m not sure exactly what they meant by that. But I’m pretty sure they didn’t have in mind the years of litigation that accompanied Ellison successfully wrestling the cup away from his longtime nemesis, the Italian-born Swiss billionaire Ernesto Bertarelli. With the trophy safely in hand, Ellison set about realizing his deluded dreams.

Drunken Skipper

As the greatest prize in yachting, the cup has long been coveted by the world’s richest men. Tea magnate Thomas Lipton tried five times between 1899 and 1930 to win the cup and never did. More recently, Ted Turner won it in 1977, though he’s probably better remembered for turning up drunk at his post-victory news conference than for the race itself. Now there is Ellison, the founder and chief executive officer of Oracle Corp., who has spent hundreds of millions of dollars over the years in pursuit of the cup. He won it three years ago and will defend it this summer.

Ellison, however, is no ordinary billionaire. He is a Silicon Valley billionaire, and thus sees it as his sacred duty to disruptively innovate -- or is it innovatively disrupt? -- every industry he can, whether it be software or yachting. The America’s Cup was the perfect vehicle for his entrepreneurial evangelism: One of its quirks is that the winner of the last race basically gets to set the rules for the next one.

What Ellison wanted was bigger, faster boats. Specifically, 72-foot-long catamarans with massive, computer-controlled fixed “sails.” (They’re not sails that you or I would recognize, the sort that billow in the wind. More like the wing of a Boeing 747, only upright and 13 stories tall.) The boats can travel up to 50 miles per hour, riding above the surface of the water on rudders and carbon-fiber blades. Is this even “sailing”?

Ellison liked these big, fast boats because he thought they would make better television. And he was sure that sailing belonged on television. To that end, he hired the mastermind who brought the virtual first-down line to the NFL’s broadcasts and the glowing hockey puck to the NHL’s. Ellison was going to turn sailing into a spectator sport. Even if that meant buying the airtime himself to get any of the races leading up to the cup -- the “America’s Cup World Series,” as he called them -- on TV.

Where do Ellison’s dreams of revolutionizing sailing stand now, with the start of the competition just weeks away? Instead of 15 teams contending for the cup, as he had imagined, there are just four. (Bertarelli is among those who dropped out.) There are two main reasons for this.

Frightened Crew

First, amazingly enough, it turns out that not even yachting billionaires are prepared to spend the $100 million it takes to build and maintain boats that meet Ellison’s absurd specifications. Second, it turns out that sailors don’t necessarily want to sail them. Last month, one of the boats capsized, killing the British Olympic gold medalist Andrew “Bart” Simpson. (Like “sail,” the term “sailor” may need updating: These aren’t guys in polo shirts and Sperry Top-Siders. America’s Cup racers now wear padded body armor and crash helmets and carry oxygen tanks.)

Of course, no story of a megalomaniacal billionaire imposing his will on a sport would be complete without the fleecing of taxpayers. The city of San Francisco has spent millions to redevelop its waterfront for the race, even as it has come to grips with the reality that Ellison’s promises of “economic activity” around the cup were mostly just hype. Russell Coutts, his team’s CEO, is now acknowledging that mistakes have been made, and suggesting that whoever wins this year’s cup will probably opt for smaller, safer boats.

That’s a start, but it’s hardly enough. In Silicon Valley, they like to say that failure is a prerequisite for success. In yachting the lesson is slightly different: Innovation doesn’t always equal progress. Also, it may be possible for one man to singlehandedly destroy the sport’s oldest and most famous race.

So no hard feelings, Larry. But maybe yachting would be better off if you spent a little more alone time on that Hawaiian island of yours. In the meantime, the America’s Cup can go back to wooden yachts and Newport, Rhode Island, where it belongs.

(Jonathan Mahler is a sports columnist for Bloomberg View. He is the author of the best-selling “Ladies and Gentlemen, the Bronx Is Burning” and “Death Comes to Happy Valley.”)

To contact the writer of this article: Jonathan Mahler at jmahler11@bloomberg.net or @jonathanmahler on Twitter.

To contact the editor responsible for this article: Michael Newman at mnewman43@bloomberg.net.