Ellison is that kind of adversary - a polarising figure who attracts as many detractors as acolytes for the winning-is-all mentality he applies to both business, as chief executive of software giant Oracle Corporation, and sport.
His hard-nosed business ploys have brought insane wealth - estimated at US$43 billion ($54 million). He was paid US$90.7 million last year, way beyond any other American CEO. He has spent hundreds of millions pursuing and securing the America's Cup (winning at his third attempt) and now defending it. Less well-known is his contribution to medical research and other charities.
He's a snazzily-dressed maverick; a non-conformist who found his feet in the technology revolution in the 1970s and became Silicon Valley's most flamboyant personality. He married and divorced four times. Success does not seem to have remoulded him and, at 69, he remains as politically incorrect as he is driven - and looks 10 years younger.
"He's a brilliant guy who is misunderstood," says San Francisco Chronicle feature writer Julian Guthrie, who enjoyed rare access to Ellison for a book on his cup quest, The Billionaire and the Mechanic.
"He is motivated relentlessly," Guthrie told the Weekend Herald. "His company won the race for relational database storage (for business networks), he's won the America's Cup - but he's always looking for the next challenge. For him, it's all about testing his own limits and finding out what he's really capable of."
His ascent to the cream of the world's richest is pure American Dream. Born in a working class area of Manhattan to a 19-year-old single mother in 1944, he nearly died of pneumonia as an infant, at which point his mother thought it best to adopt him out to an aunt in Chicago. His biological father, an airforce pilot of Italian heritage, was never traced. His elderly adoptive father, who'd lost his savings in the Great Depression, never warmed to the boy.
"His stepfather told him all too often that he would never amount to anything," Guthrie says. "He's motivated by that need to prove himself against the naysayers. He has this great line: 'I had all the disadvantages I needed to succeed'."
His school years were noteworthy for poor grades and his questioning of authority.
"I was a quick-witted and aggressively glib teenager," he recalls in a 2003 biography by Matthew Symonds, Softwar: An intimate portrait of Larry Ellison and Oracle.
"(Teachers) constantly made mistakes and I enjoyed pointing them out. They didn't like that." But in computer programming, he found "the only thing that matters is results".
For at least two decades, Oracle has been to business computer systems what Microsoft is to the PC; its software is a ubiquitous if largely invisible part of integrated networks. More important than innovation was Ellison's corporate raider strategy - buying out competitors such as Sun Microsystems. His rivalry with Microsoft boss Bill Gates is legendary, his company once using detectives to go through Microsoft's rubbish in a bid to expose underhand tactics in an anti-trust case. The litigation which is such a drag on the America's Cup is routine to Ellison the businessman.
He is also a rare example of a tycoon chasing a sporting trophy who has genuine credentials in the sport. And he's done that by working closely with New Zealand sailors and boatbuilders.
Chris Dickson, our first America's Cup hero, spent 10 years driving Ellison boats, first on Sayonara, which dominated the maxi racing circuit with a largely Kiwi crew, then through two America's Cup campaigns.
"He's an excellent big-boat yachtsman and helmsmen," Dickson says. "He's an intelligent guy - he knows what he doesn't know and when he wants to learn something he learns from the best. He's always the first person to put his hand up and say 'I don't know'."
Dickson recalls the final race in a maxi world series off Bermuda, when Sayonara fell behind and seemed destined to finish second overall. Ellison drove the boat away from the fleet in search of a wind change. "We kept doing the numbers on when to gybe and calculated we would still finish second. He kept saying there was no point in coming second so we kept going and going until it got beyond ridiculous; we were going to come in last. Then the wind changed, we gybed and won. Never give up as long as there's a glimmer - that's Larry."
Though notorious for quickfire sackings, Ellison's pursuit of perfection does not turn vindictive when things go wrong, Dickson says. "His attitude is: 'if it's not working, let's change it - either you change it or I change it'. He's not one to hesitate."
Oracle's boatbuilding subsidiary, Core Builders Composites, is led by Kiwis Mark Turner and Tim Smyth who were closely involved in construction of the 90ft trimaran that secured the cup for Ellison. In 2008, the company set up their high-tech shop in Warkworth and, at Ellison's urging, the 15 AC45 catamarans used in the America's Cup World Series and many components for Oracle's two AC72 catamarans were made there. Smyth reckons Ellison has directed nearly $150 million in foreign investment and export sales New Zealand's way in 12 years.
It was inevitable that Ellison would push the America's Cup to new extremes both on and off the water - in use of technology and litigation. After two "failures" - in 2003 when Oracle was the beaten challenger series finalist in Auckland and in 2007 - he adopted a "hire the best to be the best" approach and brought in New Zealander Russell Coutts. Oracle then launched a direct "deed of gift" challenge which triggered two years of bitter and convoluted legal jousting with erstwhile friend Ernesto Bertarelli, the billionaire behind the Cup-holding Alinghi syndicate. Finally, Ellison was cleared to pitch his trimaran with its revolutionary wing sail against Alinghi's catamaran. After the mismatch, Ellison and Coutts pledged to create fair rules; an event affordable for others, and to take the sport to a new audience with high-speed catamarans with wing-sails and high-tech equipment. Up to 15 challengers would come to San Francisco Bay for an extravaganza that would revitalise the waterfront, attract millions of spectators and generate US$1.2 billion in economic activity. Plans were dramatically scaled down after only three challengers emerged and fallout began over who would pay for facilities. The envelope-pushing designs had made participation unaffordable and concerns about safety boiled over in May when Swedish challenger Artemis capsized and sailor Andrew Simpson drowned.
Ellison has described his life as surreal. Mike Wilson, author of the 2003 book The Difference between God and Larry Ellison, argues differently. "His rise to fame and fortune is a tale of entrepreneurial brilliance, ruthless tactics and a constant stream of half-truths and outright fabrications for which the man and his company are notorious."
For all his phenomenal success, there have been other occasions when he's promised more than he's delivered - such as the Auckland press conference when he outlined plans to set up an Oracle Corp research and development branch in Northland. Many San Franciscans are similarly puzzled about the city's hosting experience to date, though Guthrie stresses it is still expected to pour US$900 million into the county's economy.
One contribution that all approve of is the advanced television coverage, with on-board sensors, cameras and microphones meeting graphics wizardry to make the racing dramatic and easy to follow.
Critics say San Franciscans' lukewarm response to the event won't bother Ellison, whose only focus is keeping the Cup in his trophy cabinet. Guthrie disagrees. "He's more sensitive than people think. He wanted to stage the event in San Francisco where there's this natural amphitheatre so people can watch from the shore.
"He's given up trying to sway public opinion. But he wants it to be a success - for people who don't understand what a tack or a gybe is to look at it and say 'this is pretty cool'. He wants there to be great sailing."
And should he lose? Those who know him say it would be no surprise if he walked away, satisfied with what he's achieved.
Says Guthrie: "There's that constant need to push the limits and move on."
Larry's accessories
• His US$150 million compound outside San Francisco was modelled on a Japanese palace, with a forest of cherry trees and a lake filled with mineral water.
• He collects Samurai body armour.
• Toys include fighter planes (he is a licensed pilot), sports cars (including a McLaren Formula One), a succession of maxi racers and super yachts.
• He owns a tennis tournament, at Indian Wells, which attracts the world's best.
• He bought the Hawaiian resort island of Lanai for US$650 million last year and plans to turn it into a model of sustainability.
