Microsoft-Yahoo the mother of all clusterbombs

Seeing how I need to be in tip-top condition to view a New York Giants' upset on Sunday, I've settled on "clusterbombs."

You get the idea.

Am I being overly grumpy? Since we're going into Super Bowl weekend, I was reminded that when the Dallas Cowboys traded Herschel Walker to the Minnesota Vikings in October 1989, most football experts thought the Cowboys got the raw end of the deal. They had dealt away perhaps the best running back in the game in return for a collection of no-name role players and six future draft picks. The upshot: Dallas won three of the next eight Super Bowls while the Vikings are still on the schneid.

But software is a harder contact sport than football, and for Microsoft to pull this off, Microsoft CEO Steve Ballmer will need to throw one hell of a hail mary pass. Naturally, the big money players are rooting for him to be successful. This is a deal armchair strategists and Wall Street stock pumpers have been in love with for the last couple of years. Yahoo's been a weak stock and they'd love to make a profit on what's been a lousy investment.

Take a gander at the early analyst reactions pulled together by Henry Blodget over at Silicon Alley Insider:

Imran Khan at JP Morgan: "Microsoft and Yahoo will likely encounter little resistance from regulators, since their combined share of the search market would only be around 30% compared to Google's 60%. The combination would give Microsoft much needed scale, which would be invaluable in challenging Google...Further, we believe the increased scale of the combined search entity would lead to improved monetization due to a number of advertisers, which positively impact coverage, click-through rates, and pricing. Microsoft's command of access points through Windows, Xbox, and Internet Explorer would enable it channel yet more search. This is a crucial synergy."

Citi's Mark Mahaney: "For Microsoft or any other company seeking to gain scale in Internet advertising, Yahoo is an obvious strategic choice given its position as one of the top 3 Web properties worldwide." Citi cautioned against over-enthusiasm, noting that while the prospective merger would "pose a greater competitive risk to Google. But near-term, we'd be skeptical that search users' overwhelming preference for Google would change."

Sandeep Aggarwal, Oppenheimer: "We believe that in the long run both Microsoft and Yahoo as a combined company might emerge as a stronger competitor for Google, but lots of developments would have to take place before that happens.

• Google owns nearly 75% of the search market and Microsoft and Yahoo together own nearly 18% of search marketing.

• Display advertising is the second largest online ad format at 33% of total worldwide online advertising. Google currently owns less than 2% of the display market (with DoubleClick this would increase) and Microsoft and Yahoo together own nearly 30% of display market.

• With this move, the likelihood of the EU rejecting Google's acquisition of DoubleClick goes down.

• Regarding VCLK, as the largest independent ad network, we view them as a beneficiary of industry consolidation and a leading takeout target."

And on paper, at least, you could make a plausible argument on behalf of doing a deal. Ballmer gave voice to the bigger-is-better crowd, contending on the conference call earlier Friday that the combination will translate into increased scale and capacity (at least from a consumer perspective).

In other words, 1 plus 1 equals 2 (and whatever extra can be squeezed out). That equation may add up in the field of standard mathematics, but this is the real world. The deal makers at Microsoft say they know what they're doing but they're competing against history. Even if a reconstituted "MicroYahoo" doesn't wind up in the Bonehead Hall of Fame along such stinkers as Excite@Home, Yahoo-Broadcast.com (which saddled us with Mark Cuban forever!), Compaq-DEC, and, of course, AOL-Time Warner, this will be a huge headache.

Yahoo had its day in the sun. That's over. These days Yahoo is a severely dysfunctional, overstuffed company riddled by an indecisive bureaucracy.

Jerry Yang, who last year returned to take the helm after Terry Semel got sent into a platinum retirement, doesn't have a clue how to dig the company out of its hole. If he wasn't the guy to run Yahoo when Tim Koogle was CEO, why is Yang the guy to be No. 1 now? Since taking over, he's mumbled his way into a bigger disappointment that I ever expected. From a Yahoo perspective, the best thing now would be to take the lifeline tossed its way from Microsoft and let Ballmer handle the mess that awaits.

So if Microsoft ends up with the prize, save the early celebrations. The uneven track record of big technology deals over the last decade or so suggests that this will tax the company's managerial talents more than at any point in Microsoft's history. Don't forget that the impetus behind the buyout bid stems from Microsoft's woeful inability to compete against Google. Is Steve Ballmer really that much smarter than Steve Case?