Michael Dell could be about to square off against a ruthless new adversary over his proposed buyout of the company that bears his name, with reports suggesting that the infamous corporate raider Carl Icahn is buying up shares in a last-ditch bid to scupper the deal.

CNBC reports that Icahn, who has a well-deserved reputation for throwing a spanner in the works of every company he touches, has seized the opportunity to amass some 100 million shares in Dell, which if true, would give him a 6 percent stake in the company.

Dell’s bid to go private has already met strong opposition from some of the company’s key investors, chief among them Southeastern Asset Management, which claims that the price-per-share offered by CEO Michael Dell is well short of the firm’s true valuation. Only yesterday, Southeastern delivered a strongly-worded letter to Dell’s shareholders, criticizing the deal for favoring the management at the expense of everyone else.

In spite of its vehment opposition, Southeastern lacks the clout to block the deal alone, as it only controls 7 percent of the company. While it’s gathered support from some quarters, most notably T. Rowe Price Group, which owns around 5 percent of Dell, it’s still not enough to derail Michael’s plans.

But if reports that Icahn has taken a 6 percent position in Dell are to be believed, this could well prove to be a game changer as it would make him the third largest shareholder in Dell, behind only Southeastern and Michael Dell himself. Should CNBC’s assertion that Icahn plans to block the deal be correct, this could suddenly give naysayers enough clout to force Michael Dell to back down.

There’s a problem with this theory though – it goes against all that Icahn is known for. The investor has a history of raiding companies and forcing them to take action that raises their share price, so that he can quickly cash in on his profits, but by scuppering the Dell buyout its share price would almost certainly fall.

What’s Icahn Up To?  3 Possible Scenarios:

According to CNBC, Icahn’s plan is to pressure Dell into a leveraged recap rather than a buyout. Icahn wants Dell to remain public yet take the loan money offered by the banks, using this to fund a massive dividend for investors. The only problem with this plan is that Michael Dell would be dead against it – he’s been screaming from the rooftops he doesn’t want to be CEO of a public company anymore – but that’s exactly where Icahn’s plan would leave him. Having a frustrated, angry CEO probably wouldn’t be good for Dell’s prospects going forward, but at least Icahn would get a nice pay-off.

A second theory is that Icahn might just have made a snap decision to wade in and force Michael Dell to up his offer from $13.65 a share. The CEO has both the means and the motivation to do so, but whether he’d be willing to raise his offer by enough to make it a worthwhile investment for Icahn remains to be seen.

There’s also the possibility that Icahn’s just using his opposition to the deal as a smokescreen, in order to get in on the deal himself, although this would seem the least likely scenario. Icahn isn’t really known for taking the role of a minority participant in his deals, but then again, perhaps he’s mellowed in his old age? From Michael Dell’s viewpoint, this would actually be welcome, giving him the leverage he needs to see off any threats to his dream.