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Amid the ongoing tumult in the saga of the potential buyout of Yahoo by Microsoft, Carl Icahn has done his best to make sure that his opinions do not go unnoticed.

The multi-billion dollar man who has made it his business to seemingly bully struggling companies into succeeding –all while making a hefty profit for himself in the process–has made Yahoo his most recent and most newsworthy project to date. What still remains uncertain is whether Icahn’s efforts are helping or hurting not only a potential merger between the two behemoths but also the general welfare of Yahoo, of which Icahn owns 4.3% in stock. Since purchasing his stake, Icahn has vocally undermined current CEO Jerry Yang, criticized the handling of the Microsoft buyout offer and generally disagreed with the direction that Yahoo has been taking as a company in a series of bilious open letters to the Yahoo board of directors.

What is clear is that Icahn wants one thing: to make money on his investment in Yahoo. What is also clear is that he believes that the only way that this can be accomplished is with either a sale to Microsoft or with a complete change in the current administration at Yahoo. The former is the route that Icahn would most like to take, however, the latter is an option at which the staunch Icahn is unlikely to balk. What is unclear is the efficacy of Icahn’s campaign. His attitude has more than ruffled Yang’s feathers and the two have been exchanging sorties throughout the process. In the battle of the billionaires, though, there seems to be one notable absentee, namely, Steve Ballmer, Microsoft’s brash CEO.

In a letter to Yang on May 3rd, Ballmer made it abundantly clear that he was very disappointed in the way that Yahoo had addressed the buyout offer from Microsoft, which he deemed “the only alternative put forward that provides [Yahoo’s] stockholders full and fair value for their shares.” Although Microsoft has not completely dismissed the idea of a partnership with Yahoo, it is interesting to note that Ballmer has stayed mum since his letter over one month ago.

At this point, the loudest voice in the room is neither that of the CEO of Yahoo nor Microsoft, but rather that of Carl Icahn. Whether or not one believes Icahn to be right–and he certainly has his supporters among Yahoo shareholders–one has to wonder whether or not this seasoned but souring veteran of the business world is increasing or decreasing the likelihood of a merger. One look at Icahn’s track record inspires confidence that he not only has done this before, but he’s well-equipped to do it again. However, with three multi-billion dollar egos involved in the decision-making process regarding two of the Internet’s most prominent brands, it remains to be seen if Icahn is up to the task this time around.

Only the future will tell for sure, however, it should be noted that Icahn’s success or failure in this arena will most certainly go down as either his greatest achievement or his biggest flop to date. At the very least, we will get an answer to the question: what is the best way to catch billionaire flies? Convention suggests that honey is your best bet, although Icahn seems to be betting big on vinegar. If he ends up proven right, it could change the way that business is conducted between the Internet’s power elite.


2 thoughts on “Anything You Can Do, Icahn Do Better
  1. Very entertaining blog Mike! Even though I do not agree with Icahn’s rude and overly agreesive business approach, I do in some strange way admire his insane motivation and strength in the Internet world. I predict the notorious business mogul will in fact strike again but to what extent I cannot say. However, I am very curious to see what actually plays out as this dramatic saga continues.

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