That isn't as ridiculous as it sounds! While I listened to the conference call of the deal with Yahoo, a couple things seemed to stand out to me. The ad industry wants an alternative to Google (Is it unusual that advertisers don't want to deal with the company whose motto is "Do no evil?" ) and MSFT was encouraged by media companies to make an acquisition like this and they received positive "unsolicited feedback this morning from publishers and advertisers."
Yahoo already has partnerships with 555 daily papers; why not seal the deal by buying the NY Times? Go back to aQuantive. MSFT bid $6 billion for them on option expiration on May 18th, 2007, and then two months later, they bought AdECN. Obviously synergistic. Yahoo bought 80% of ad exchange company Right Media that they didn't own for $680 million on April 30, 2007. (In October of 2006 they picked up 20% of the company for $30 million.) MSFT's price for AdECN was undisclosed, but using YHOO's metrics, (and the $347 million MSFT spent on undisclosed acquisitions) I would guess it would be around $140 million. Now Mister Softee has the ad exchanges!
So add the Times to their portfolio and get the paper that matters! Wouldn't this complement the content from Yahoo, and increase it's advertising platform? It also works linguistically. Yahoo's name came from the "rude, unsophisticated, uncouth" humanoid creatures known as Yahoos of which the super intelligent well reasoned horses called Houyhnhnm's ruled over in Jonathan Swift's 1726 classic, Gulliver's Travels. A hundred years ago, the anti-intellectual right wingers were known as "Yahoo's." As everyone knows, the Times nickname is "the old gray lady," the province of the intellectuals and left wingers.
Remember back in 1999 when Mister Softee invested $5 billion in ATT? Oh that's right. Nobody remembers that. Do you think anyone will forget it if MSFT spent $5 billion on the Times?
The "old gray lady" with the "Yahoo's!" The left with the right. The intellectual with the anti-intellectual. Bought will Bill Gates money! You couldn't make that up!