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Five reasons Oracle/PeopleSoft was more fun than Microhoo

As Microsoft's takeover attempt of Yahoo lurches toward an alleged deadline, some writers pine for a far more flamboyant fight from five years ago.

As the Saturday deadline looms for Yahoo to give Microsoft an answer on the latter's takeover bid, it's time for those of us writing about this to admit something: This is getting boring.

I mean "boring" in that Village of the Damned or Groundhog Day way, in which we're doomed to write the same story over and over and over again. Tomorrow, Yahoo may or may not respond to Microsoft with a carefully worded letter. Sunday, Microsoft may or may not respond with a carefully worded letter. Monday, The Wall Street Journal, which we suspect has a bat phone to Yahoo corporate PR, likely will publish yet another article quoting "people close to Yahoo" with another plan to wiggle out of Microsoft's grip.

We will dutifully cover all of it, and we will be bored. You know what this fracas really needs? Larry Ellison.

Ellison could make Microhoo interesting

Oracle's Ellison, of course, made a fine show of his hostile takeover of rival software maker PeopleSoft back in 2003. It was all vinegar from the start. Ellison mused about the thousands of PeopleSoft employees he'd have to lay off; the PeopleSoft customers who would be forced to migrate to Oracle software (the reality turned out to be much more accommodating); and at one point mused that if he had one bullet, PeopleSoft CEO Craig Conway's dog would be perfectly safe, but Conway could have some problems. (When Ellison made that crack in an analyst presentation, I was sitting behind an Oracle corporate PR person who made a sound something akin to "AIEEEEE!!!")

Conway responded by appearing on stage a few days later with his dog--both of them wearing bullet-proof vests. That's good stuff! So in the spirit of the real animosity that consumed that takeover, rather than the passive-aggressive testiness between Yahoo and Microsoft, here are five reasons the Oracle/PeopleSoft fight was so much more fun than this one:

The hostility was no act. Yahoo's Jerry Yang has made it clear he'd sooner kiss a Wookie than sell his company to Microsoft. But at PeopleSoft, there was genuine hatred for Oracle. You couldn't have two more different companies. PeopleSoft was viewed as the people-friendly company. Its core market was human resources software. Oracle was Oracle, with a well-earned reputation for cutthroat competition inside and outside the company. Its core market was databases and financial software. People...who needs people?

That's not to say the PeopleSoft people were pushovers. They were known to chant "Kill Oracle!" at corporate pep rallies, and were just as eager to brawl over big customers; their suits just weren't as fancy.

Craig Conway worked for Ellison

The Oedipal angle. At the time of the takeover fight, the CEOs of at least four major software companies had started their executive careers at Oracle, including PeopleSoft's Conway. Say what you want about Ellison, but he's good at spotting talent, and unfortunately turning that talent into rivals as they get older. That's what he had in Conway, a smart, aggressive executive who would, ummm, sooner kiss a Wookie than sell out to Ellison. I suppose you could make all sorts of Luke Skywalker/Darth Vader metaphors here, but I'll spare you the pain.

Ellison, the swashbuckler of software. Everyone loves a good show, and Ellison delivered. Besides the initial salt-of-the-earth musings and gunplay discussion, Ellison, the billionaire yachtsman, showed few executives can swagger like he can.

When he testified at an eventual antitrust trial that could have blocked the PeopleSoft takeover, Ellison arrived in celebrity style (with cameras swarming outside the federal courthouse in San Francisco where the trial was held) in a natty charcoal suit with patriotic red tie. On his way to the witness stand, he swiped a bottle of water off the Justice Department lawyer's desk, sat down, opened the bottle, and took a deep, satisfied swig. It was a moment of pure arrogance. Classic Ellison.

Dave Duffield, savior of kittens and puppies. Conway was the chief exec, but Duffield, PeopleSoft's founder, was still chairman of the board. Duffield's public persona was the antithesis of Ellison. He often signed his name with his initials, D.A.D., and that's how many longtime employees viewed him. Duffield had a reputation for lavishing his fortune on animal shelters, while Ellison had a reputation for lavishing his fortune on himself. They were the yin and yang of software.

Dave Duffield, PeopleSoft's founder, animal advocate Workplace

Oracle fought the law and Oracle won. Perhaps it's unfair to say the Justice Department prosecutors who tried to block Oracle from buying PeopleSoft were bumbling, but from the outset, their case seemed shaky. The federal judge presiding over the case started grilling them during opening statements, and didn't let up for the duration of the trial. Now I'm not ever going to argue that Oracle was an underdog, but for the anti-establishment types in the press corps, it was awfully interesting to see a government argument unravel so quickly.

Of course, there's still a very good chance Microhoo could draw government scrutiny. But I have no faith in the folks from Redmond (who have a long, painful track record with this sort of thing) to flamboyantly thumb their noses at the feds the way Oracle did.

So here's my plea to Ellison: Please, get involved, become Yahoo's white knight. It's not too late. Time-Warner's AOL and News Corp. (and probably Google, too) are just playing footsy with Yahoo. There's an opening for you. This is a great opportunity to piss off Ballmer and Gates & Co. Sure, you've got lots of other acquisitions to deal with, but you'll figure this out.

Help us, Larry Ellison. You're our only hope.