Ellison retrospective: An original straight out of central casting

It will be a long time before central casting provides the tech industry with another CEO like this one.

Whatever the business implications of Larry Ellison's surprise resignation as Oracle CEO, this much is clear: his departure leaves in its wake a horde of brokenhearted headline writers around the world.

Over the course of a four-decade plus career, Ellison cut a bella figura. And in an industry marked by turbulence and near-constant change, Ellison has proved to be great copy as he clawed and grasped and battled to build Oracle into one of the biggest and most successful software makers in the world.

There's an old joke once popular in Silicon Valley asking what's the difference between God and Larry Ellison? The answer: God doesn't think he's Larry Ellison.

After all, how many billionaires can you name who can visit their own Hawaiian island and with a yacht that also won the America's Cup? Or fly an SIAI-Marchetti S.211 fighter plane, used by the Italian Air Force. (At one point, he even tried to import a decommissioned Russian MiG-29, but the U.S. government said no. "It's considered a firearm, even though that's not my intention," he said. "It is disarmed, but theoretically you could rearm it and take out a couple of cities."

There are many signature Ellison moments like these over the years. But it's a narrative that testifies to a complicated multi-sided personality who -- whether by design or happenstance -- has earned a spot in the annals as one of those larger-than-life types who will be remembered for a long time.

The Microsoft Dumpster diver

"It's absolutely true we set out to expose Microsoft's covert activities," Ellison boasted in June 2000, while confirming that Oracle had hired a detective agency to find information about Microsoft-funded organizations opposing the government's effort to split up the software giant.

"I feel very good about what we did...Maybe our investigation organization may have done things unsavory, but it's not illegal. We got the truth out."

'Larry, stop spending like a drunken sailor'

Well, not exactly a drunken sailor but Ellison's spending had reached the point in 2002 where his accountant, Philip Simon, warned him to start throttling back on a lavish lifestyle that was costing him around $20 million in yearly expenses.

"I'm worried, Larry..." Simon wrote to Ellison in an e-mail. "I think it's imperative that we start to budget and plan.

Turns out that Ellison had financed his spending by borrowing against his stock ownership in Oracle -- a habit that maxed out his credit limit of more than a billion dollars.

"I know this e-mail may/will depress you," Simon wrote. "However, I believe it's my job to address issues you'd prefer not to confront. You told me years ago that it's OK to raise the 'diversification issue' with you quarterly....Well, I'm doing so. View this as a call to arms."

Let's buy Lanai

In 2012, Ellison bought most of the Hawaiian island of Lanai, well, because he could. So there. It didn't hurt that the purchase also shut out Bill Gates, who rented the island in 1994 for his wedding and figured in rumors as another potential bidder.

Sportsman of the seas

An avid yachtsman, Ellison's Oracle Team USA won the America's Cup in a nail-biting 2013 finish with the team from New Zealand. Ellison previously owned one of the world's largest luxury yachts. But it was too big to moor for many docks and so he sold it to record industry mogul David Geffen.

Buzzing San Jose

Ellison sued the city of San Jose, Calif., to challenge a city curfew preventing him from landing his private Gulfstream V at the local airport between 11:30 p.m. and 6 a.m. due to noise considerations. After four years of fighting, Ellison ultimately moved his plane to Stockton, Calif.

SAP's on drugs: Get me some of the same

Truth be told, the tech industry circa 2014 is so scripted that we've reached the point where boring is the best we can hope from a CEO's public comments. But throughout this long career, Ellison relished any opportunity to offer pungent disses of competitors -- even on quarterly earnings calls. In March 2012, Ellison veered from a high-end discussion of enterprise-level applications to lob a few bombs in the direction of rival SAP.

"Six years ago we made the decision to rewrite our ERP and CRM suit for the cloud. We called it Fusion. SAP called it confusion," Ellison said. "It will take years for SAP to catch up."

He followed that bon mot up with this precious jewel:

'When SAP, and, specifically Hasso Plattner, said they're going to build this in-memory database and compete with Oracle, I said. God, get me the name of that pharmacist, they must be on drugs."