Microsoft (NASDAQ:MSFT) has a thing for losers.

Barnes & Noble's (NYSE:BKS) Leonard Riggio is the latest disgruntled founder to want to privatize his struggling company. In an SEC filing yesterday, Riggio revealed that he aspires to acquire his company's flagship bookstore business.

Riggio wants the retail chain and the related website. He's the board's chairman and owns 30% of the outstanding stock, so one could reason that he knows the company pretty well. You know what he doesn't want? Riggio has no interest in acquiring the fledgling Nook and meandering campus bookstore business that Microsoft bought into last year.

Yes, Mr. Softy seems to be left holding the bag on the struggling e-book platform and a chain of college bookstores that's growing obsolete as schools turn to digital textbooks.

It's not the first time that Microsoft has shelled out big money for a laggard.

Earlier this month Microsoft agreed to kick in $2 billion in the proposed $24 billion deal to take PC giant Dell (UNKNOWN:UNKNOWN) private.

One can always argue that Microsoft's investments were either opportunistic or tactical. Buying into the Nook could've swayed Barnes & Noble to abandon Android for its Nook tablets. It didn't. One can hope that Microsoft's investment in Dell will keep it from cranking out Android tablets and smartphones. It won't.

Previous 10-figure commitments have been tethered to conditions.

Microsoft agreed to reward Yahoo! handsomely in exchange for letting Bing take over the portal's search business. Microsoft has promised Nokia (NYSE:NOK) "billions" for its support of Windows Phone 8.

However, isn't this a pretty sad lot?

A portfolio of Barnes & Noble, Dell, Yahoo!, and Nokia may have been great in the 1990s, but all four companies have had rough years lately. Yes, some of them have rallied recently, but the four companies still lag their peers.

Why is Microsoft partying like it's 1999? Why is it getting fixed up on DotComBubbleMingle?

Yes, once in a while Microsoft does manage to make an early investment in a fresh market leader, but there are too many lovable losers on its list. The world's largest software giant needs a new matchmaker.

Longtime Fool contributor Rick Aristotle Munarriz has no position in any stocks mentioned. The Motley Fool owns shares of Microsoft. Try any of our Foolish newsletter services free for 30 days. We Fools may not all hold the same opinions, but we all believe that considering a diverse range of insights makes us better investors. The Motley Fool has a disclosure policy.