The Price of Crossing Steve JobsS

Gordon McLeod has been packing up his office; today is his last at the Wall Street Journal. His ejection is complicated. But some coworkers think they know what did him in: insulting Steve Jobs in Rupert Murdoch's presence.

McLeod's exchange with Jobs, the fiercely willful Apple CEO, came one night this past June, at Murdoch's ranch in Carmel, California. An annual News Corp. retreat was under way and the theme, at least for the evening in question, was apps of the sort that run on Jobs' iPhone and iPad.

The Price of Crossing Steve JobsS

Jobs arrived for dinner by helicopter. He stayed maybe an hour; two tops. But he left an outsized impression, and not an entirely pleasant one: Even accounting for his reputation, some present were struck by what they saw as his arrogance and disdain. Over the past three decades, Jobs has left plenty of people feeling that way — underlings, competitors and especially journalists. But in Carmel (pictured, right), the assembled crowd had a reason to take it personally:

In a Q&A session with the assembled executives and managers, including Journal editors, Jobs railed against the apps newspapers like the Journal have created for his iPad. Their interfaces are terrible, he said, and their content is all too often limited . That the Journal's archrival the New York Times was among those singled out for criticism — Jobs hates the limited NYT Editors' Choice app — must have helped take the sting off. And Jobs did praise the WSJ's iPad app as very attractive. But the CEO also said the app was too slow, essentially calling it a clunky reading experience.

It was on this point that McLeod, who wouldn't comment for this post, is said to have engaged with Jobs. As president of the Wall Street Journal Digital Network, McLeod was at least a player on the paper's iPad strategy as well as a spokesman for it. It's not clear whether the Time Inc veteran got into it with Jobs during the more public Q&A or in a more private meeting afterward, but there was definitely a back and forth between the two men in front of other News Corp. hands: Word of McLeod's purportedly impertinent comments challenging Jobs ricocheted around the company almost instantly.

Jobs' visit to Murdoch's ranch was perhaps a more delicate occasion than McLeod had realized. On the one hand, you have a tightly wound tech executive — one with a rocky history with the Journal. It was the Journal's deputy managing editor who infuriated Jobs by tweeting from a prototype iPad that Jobs brought to the newspaper's office after the device was unveiled but before it was available for sale.

The Price of Crossing Steve JobsS

On the other hand you have News Corp. chairman Murdoch, an old school media mogul with, by all accounts, a huge admiration for Jobs and, in particular his iPad. Where Murdoch's digital nemesis Google specializes in indexing and aggregating free content and in offering free services, Jobs has built a brisk business selling old fashioned content for consumption on newfangled devices. Murdoch has called Jobs the best CEO in America.

That feeling is so genuine, some insiders believed, it's possible Murdoch would have seen any questioning of Jobs' statements as an insult to Jobs. The Apple CEO, after all, had been invited to hold forth, not necessarily to attend a press conference. (Wall Street Journal editor and ranch regular Robert Thomson was among those at News Corp. who declined to talk to us about McLeod's encounter and how it was received within News Corp.)

Or maybe McLeod really was over the line in whatever he said. Perhaps Jobs, who can be as icy as he is fiery, made it clear he felt insulted. It's not clear exactly how he reacted.

In any case, McLeod was not long for News Corp. Following the June Jobs encounter, his departure was announced publicly in early September. With no new gigs lined up and an avowed interest in finding similar work to tackle, McLeod did not appear to have planned his resignation.

It's widely agreed within the company that McLeod was not pushed out simply because of a conversation with Steve Jobs. There were other reasons the four year veteran didn't seem like the best fit for the company, which is trying to rapidly evolve its digital offerings. By some accounts, the Journal and News Corp. high command was already on the fence about whether they needed him prior to the Carmel retreat. There is a contingent who believe the Jobs encounter may have tipped the scales against him. And that perception alone testifies to the long shadow cast by America's most famous CEO — a shadow to be feared even in a different company, in a different industry, run by a CEO of very different generation, on a different side of the country thousands of miles away. Steve Jobs is the prototypical media mogul of the 21st Century, and you'd best not forget it.

[Photos of Jobs and Murdoch via Getty Images. Photo of McLeod via AllThingsD. Screenshot of Murdoch's ranch via NZ Life & Leisure.]