The gathering, as reported by New York magazine, was booked at Pranna, a cellar basement restaurant featuring a southeast Asian menu. The restaurant wasn't tipped off that Jobs himself would be in attendance.
The Apple executive reportedly arrived wearing a a very funny hat a big top hat kind of thing, and ordered penne pasta with a mango lassi to drink, sending the staff scrambling to accommodate his unusual request. Jobs sat at the head of the table of Times executives as he demonstrated the iPad's functionality to executives in an "intimate, family-style gathering."
While newspaper executives are reportedly wary of entering into an exclusive deal that they fear might install Apple as the content broker of print media in the same model as iTunes' music and video businesses, they're also facing tough times monetizing their content as the Internet eats away at their display ad model.
After decades of selling their own ad space in print, they're now facing the problem of trying to make money on the web, where Google dominates ad sales and advertising space is effectively in infinite supply, and therefore worth very little. Jobs is pitching iTunes' paid downloads model to print and broadcast media companies with the iPad, an idea they like but also fear, apparently much more so than the alternative of Google's virtual monopoly on online ads.
Jobs faced similar fears in hammering out deals with music and movie executives, which balked at the company's plans to sell their content without ads at relatively low prices to an audience millions of iTunes users.
Music labels' own digital plans all failed until they teamed up with Apple in the new iTunes Store. Immediately after the company saved their future however, they began complaining about the control Apple exercised over prices and marketing, demanding that users buy songs only in albums and lobbying for "variable pricing" that would give the label suits the power to charge more for new acts and threaten their own talent with cheap pricing that would devalue their work if they didn't play the labels' game.
Movie studios similarly dragged their heels in joining the iTunes Store, with early adopters limiting the number of movies they made available and worrying about the prospect of digital downloads and then rentals hurting their lucrative DVD sales. Jobs used his influence at Disney to help pave the way for broader adoption of iTunes by other studios, but it still took years to win the movie executives over.
In print media, Jobs is now working to convince publishers to embrace digital distribution, particularly for the new larger format iPad, although Jobs also reportedly said "he likes to hold the Sunday edition in his hands."
Jobs has also brokered deals with booksellers and continues to talk with print and broadcast publishers about getting their content in iTunes and customized for use with the iPad. Clayton Morris of Fox News just tweeted today that Jobs had made an appearance at his company: "It's not everyday you walk into work and see Steve Jobs standing there."