Larry Ellison, the Oracle chief executive, has leveraged his skills as a dealmaker to become a dominant force in the technology business and the richest man in the Bay Area.

But his negotiations with the City of San Francisco over staging the America's Cup sailing competition have been anything but artful. Rather, the same arrogance and overreach that caused him to lose out on buying the Golden State Warriors basketball team have been on display.

It seems that what works in the software world, where Oracle just reported blowout earnings and its stock hit a 10-year high, is not what works in big-time sports. And if the next America's Cup happens somewhere other than San Francisco Bay, it will be Ellison's loss.

Ellison won the sailing trophy last February, and with it the right to choose the venue and write the rules for the next Cup series. Initial negotiations with San Francisco produced a preliminary agreement in September to hold the races here in 2013.

But that deal met stiff resistance from Chris Daly, a San Francisco supervisor, and other local officials who declared it was too expensive -- a taxpayer giveaway to a billionaire.

A new plan, much cheaper for the city and much better for competitors and spectators, won unanimous support from the Board of Supervisors last week. But that was only after the lead negotiator for Ellison's BMW Oracle Racing told the city that the new offer was unacceptable, and that if it didn't cough up more incentives and guarantees, the regatta would go elsewhere.

The city did make some further revisions before the vote but didn't meet all of the demands, so it's up to Ellison to make a choice. He's now shopping the new San Francisco deal to Newport, R.I. -- arguably a bad-faith maneuver in itself. Rome may be in the mix, too. A decision is expected by the end of the year.

The benefits of holding the Cup in San Francisco are so obvious that it's surprising there has been such a fuss. The Bay is all but made for big-boat sailing, its natural amphitheater promising to make the event a much more dramatic -- and lucrative -- media spectacle than in the past. That's a big lure for corporate sponsors.

Ellison lives here. His team sails under the flag of the Golden Gate Yacht Club. The America's Cup is as much about high-tech as it is about seamanship, and there could hardly be a better showcase than the shores of Silicon Valley. Already, a Who's Who of the San Francisco philanthropic circuit has signed on to help raise hundreds of millions for the event.

It's conceivable, in theory, that a huge subsidy from another city could result in more short-term profits for the America's Cup Event Authority, the entity established by Ellison to stage the races and hopefully create a long-term structure to promote competitive sailing. But the San Francisco deal -- which includes facilities improvements, long-term development rights to attractive waterfront locations, and serious fund-raising support -- is nothing to sneeze at. It's almost unprecedented in this city for elected officials, business leaders, environmentalists and community groups to unite behind a big project like this.

Ellison's team, which declined requests for comment, would say it's the city that fouled things up by backing out of the original agreement. But officials are obliged to do what's best for the city. One would think someone with Ellison's skills would recognize that trying to squeeze the last dime out of city taxpayers is not the same game as pushing Hewlett-Packard to the wall in a business deal.

People familiar with the Warriors sale say Ellison's initial bid was lower than others, and that he then came in with a slightly higher bid after the deadline, only to whine when it wasn't accepted. In this case, too, he seems to have misread the deal dynamics in a way he never does in his day job.

Ellison is notoriously abrasive and not very generous locally with his money. If he dumps the Cup deal because he didn't get everything he wanted, he'll alienate virtually every public official and major private philanthropist in town -- and undermine his effort to make the competition something more than an overblown rich men's yacht race. Strange behavior for one of the world's most successful businessmen.

This article also appears in the Bay Area edition of the New York Times.