Carl Icahn, the gunslinger of private investors, once made an investment in more than 75 million shares of Yahoo! Inc. (NASDAQ: YHOO). Now Icahn is doubling his investment position in Lawson Software Inc. (NASDAQ: LWSN) to about 8.54% of Lawson’s stock outstanding.

Icahn bought most of the shares and made it onto Yahoo!’s board shortly after the company rejected an offer of $33/share from Microsoft Corp. (NASDAQ: MSFT) in 2008. His loss on Yahoo! stock could be as high as $1 billion. Icahn resigned from the board in October 2009, just after Carol Bartz was brought in as CEO, and he has lowered his holding in Yahoo! to around 4 million shares currently. Now Icahn is doubling his position in Lawson Software, a company that develops business software. That is a particularly hot place to be right now if you’re an established software house with an established product. Oracle Corp. (NASDAQ: ORCL), IBM Corp. (NYSE: IBM), Hewlett-Packard Co. (NYSE: HPQ), and SAP AG (NYSE: SAP) are competing to see which can outspend the others.

And that’s got to be what Icahn is seeing in Lawson, a chance to get in on a company that could see some nice competitive bidding. Somehow, though, it doesn’t really compute.

At around $8/share, Lawson’s market cap is about $1.33 billion, not much less than IBM just paid for Sterling Commerce, so a reasonable premium of around 25% puts the price for Lawson at about $1.7 billion. IBM still has a lot of money left to pursue other acquisitions, and so do Oracle and HP. SAP just offered to buy Sybase Inc. (NYSE: SY) for $5.8 billion, so it might want to digest that acquisition before it looks for another.

Oracle is known to have looked over Lawson for an acquisition and did not pull the trigger on a deal. IBM probably did the same when it went after Sterling. H-P can continue to play, too, but it’s 2008 acquisition of EDS pretty well filled this hole for the company.

Icahn’s other course would be to convince Lawson’s management or shareholders that he has better ideas to create new value for them. That won’t be easy either because the company has about $227 million in cash following its $160 million all-cash purchase of a healthcare software company in January. Lawson did see operating expenses rise 19% and net profit fall by 71% year-over-year in its most recent quarter, but gross profit margin hit 55%. The company will sort that out.

Once again, unless Icahn has an ace in the hole, it’s hard to see how amassing shares of Lawson is going to be a big winner.

Tell us what you think here.

Related Articles:

• Hot Tech Stock Picks to Buy Now – AAPL, MSFT, BTN, MRVL, VIT, HPQ, STM
• Goodrich Taking Flight as Airline Production Lifts Off (GR, ITA, BA, LUV, DAL)
• WMT Stock – Walmart Buys UK Discount Retailer