Yes, even

Carl Icahn

is getting into the act. He's chairman and the largest shareholder of

Lowestfare.com

, which filed to go public yesterday.

What's 63-year-old Icahn, a billionaire financier who recently bought controlling interest in the formerly bankrupt

Stratosphere

hotel and casino in Las Vegas, doing with an online travel company?

Trying to get rid of hundreds of millions of dollars worth of

TWA

(TWA)

tickets, that's what.

Icahn received the tickets, or the right to buy tickets at a deep discount, four years ago as part of an exit settlement from his role as a large TWA investor. According to the prospectus, he turned around and formed

Global Discount Travel

to sell the tickets at deep discounts.

A year later, in 1996, he launched the Web site -- Lowestfare.com -- to book TWA flights. As the Internet boomed, the site was expanded to sell a variety of travel products, including tickets on other airlines. The Web site also struck multi-year deals with the likes of

Yahoo!

(YHOO)

and

Frommers

. In other words, Lowestfare.com is starting to look like every other travel site. Watch out,

Preview

(PTVL)

!

But to those who have tracked Icahn, this is a very Icahn-like transaction, with enough vagueness and insider dealings to warrant extra caution. (In other words, what's good for Icahn, as a public investment, isn't always good for everybody else.) Consider that the company doesn't currently have any outside directors, though two are expected. And the company's president, Gail Golden, is a longtime Icahn employee who is also viewed, in social circles, as a frequent Icahn companion.

Those, however, are just incidentals. More important is the agreement with TWA, which accounted for about 96.9% of the company's revenues in 1998. The deal ends in 2003, and the company warns, "We have no right to renew this agreement and we do not anticipate renewing this agreement."

But even before the contract ends, the company says the deal could backfire for any number of reasons including trouble at TWA (remember, it was once in bankruptcy); a change in its route system, an employee strike or changes in the fleet that would result in fewer available seats.

Oh, and in a long-running court battle, TWA is disputing Icahn's ability to sell some of the seats for leisure travel.

On the plus side, Lowestfare.com earned $13.7 million last year on sales of $224 million. (The company gets to count as revenue the face value of any TWA ticket sold because it accepts the liabilities on those tickets.) But considering the nature of this beast, those numbers are bound to come under more scrutiny.

Icahn couldn't be immediately reached for comment. Also, his firm, during registration, is in a quiet period.

Cloudy future?:

Where's

Jim Jannard

when you need him? The founder of

Oakley

(OO)

, the sunglasses maker, made a big fuss about buying millions of Oakley shares in the open market at prices higher than Oakley is now. But such grandstanding is often a smokescreen, and that appears to be the case with Oakley.

Yesterday its stock, which has been in a quiet decline, closed at 7 -- its lowest close ever.

Herb Greenberg writes daily for TheStreet.com. In keeping with the editorial policy of TSC, he does not own or short individual stocks. He also does not invest in hedge funds or any other private investment partnerships. He welcomes your feedback at herb@thestreet.com. Greenberg writes a monthly column for Fortune and provides daily commentary for CNBC.