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It Wasn't Quick

If Ballmer thought he would be greeted as a "liberator" in acquiring Yahoo, he was as misguided as the Bush Administration was about Iraq. Jerry Yang, CEO of Yahoo, wasn't just coy in response; he openly repudiated the offer, and his board backed him up. In claiming that Microsoft's bid dramatically undervalued the company—despite a 70% premium over Yahoo's pre-bid $19 share price—Yang made it clear that a protracted negotiation was only the least awful among many unattractive possibilities, including a proxy fight, a hostile tender offer, and an embarrassing implosion of the deal.

Then, when Yang and his president, Sue Decker, hit the road in March with a business plan designed to demonstrate the outsize value Yahoo could create for shareholders (forecasting a quasi-miraculous doubling of cash flow over the next three years), it was evident Ballmer had found his quagmire, and he was in for the long slog.

It Wasn't Easy

Ballmer prophesied that joining forces would yield a bounty of synergies: bringing two of the four highest-traffic Web portals under one roof; more plentiful engineering talent; enhancements in online services; and, of course, the elimination of redundant operations and staff. It sounded good—to the tune of a billion dollars in up-front cost savings. But then reality reared its ugly head. Antitrust considerations made it unlikely the combined company could unite the world's two top e-mail services—Yahoo! Mail and MSN's Hotmail—with half a billion users between them (as compared with 90 million for Google and 50 million for Time Warner's AOL). Ditto for instant messaging: The merged entity would control as much as 90% of that market.

These issues paled in comparison with the lack of cultural fit between the two players. Many Yahoo employees regarded Microsoft as the enemy. And, like a homeowner threatened with foreclosure, Yang signaled he was prepared to damage the company rather than yield to the so-called evil empire. This included striking a preliminary deal with Google to deliver ads for Yahoo's search results, essentially installing an archrival's Trojan horse in the Yahoo boardroom.

It Wasn't Fun

When Yahoo rebuffed Microsoft's opening bid, Ballmer huffed and puffed. He openly scorned the "deteriorating" performance of Yahoo's business, only to see his prey perform above expectations in the first quarter. He threatened to "go hostile," as they say, but Yahoo's board yawned over his menacing imprecations. Yet none of this compared with the scorn he encountered among his own Microsofties, who saw the offer as yet another chapter in the continuing saga of overpriced acquisitions, sluggish innovation (Zune anyone?), and ineffective online strategies.

It Wasn't Cheap

Enough said? Yes, $45 billion is a very, very big number. Leave aside that the largest acquisition Microsoft had ever made was last year's purchase of aQuantive for $6 billion. And never mind the decline in Microsoft's share price after announcing the deal meant that the combined cash and stock offer for Yahoo would be even more expensive in equity if the price stayed the same. Consider that $45 billion would be enough to buy both Ford and General Motors with nearly $20 billion to spare. More pertinently, it would be enough for Microsoft to clear the market if it went shopping for other major Net assets.

For the same money, Ballmer could roll up AOL at, say, $25 billion; either Facebook or MySpace at $15 billion; and ValueClick  at $3 billion, again with a few billion left over. And if Yahoo continues to weaken over the longer term, Microsoft could always pick over its bones on the cheap, buying what it really wanted instead of the entire enterprise.

It Was Also Wrong

Ballmer's argument for going after Yahoo was ultimately about audience. Given Microsoft's trailing performance among the Web majors in search traffic and ad dollars, it was easy to fall into the trap of believing a solution for its consumer online business was also the answer to the question of Microsoft's future. Microsoft makes its big money in computer operating systems and desktop applications. Google may be lapping Microsoft in search share and online ad dollars, but the real threat is Google Apps—its free Web-based desktop applications.

The big bucks in apps are generated among corporate users, who buy site licenses for Microsoft's Office software. Despite Google's ad-based model, success for Google Apps will pave the way for paid Web services based on site licenses rather than exploiting the corporate desktop as new real estate for ads. While Yahoo might have soothed some of Microsoft's pain on the consumer side, it would have done nothing to address the real dagger threatening the heart of Microsoft's business model.

So the market may be betting Microsoft will make another run at Yahoo (its shares are trading several dollars above the average analyst target price of $24), but don't count on it. Ballmer may go shopping again—indeed, arguably, he must—but it's not likely to be with Jerry. /BusinessWeek