Note to Barack Obama: It's stuff like this that has earned you the moniker "Obambi." (Keep up the speculative investing, and maybe they'll call you "Obooya.")

This New York Times article details a couple of sketchy-looking stock buys that Obama made. He put about $50,000 into some very speculative companies "whose major investors included some of his biggest political donors."

There are more than a few ethical issues to jawbone here, the first of which would seem to be Obama's purchase of AVI Biopharma (NASDAQ:AVII), which was hawking a bird-flu vaccine story, around the same time that the freshly minted Illinois senator began stumping for bird-flu funding on Capitol Hill. It also looks a bit sleazy that he (or his broker, as the excuse goes) was buying stock in companies backed by some of his big political donors.

But here's a bigger issue -- Obama's realization that he owned these companies (and the subsequent sale) even though he had his money in a "blind" trust. How blind is a trust that lets you know what you hold? And why are these guys (senators) allowed to invest in individual stocks anyway, when they wield so much power over funding that can, in some cases, flow directly to these companies? Incredibly, ethics rules allow it.

Those rules ought to be changed. Yesterday. And if Obama wants to be taken seriously as a reformer, maybe he ought to hold himself to a higher standard. How about mutual funds only, Barack? Indexes, even?

The issue is bigger than the dollars involved, which aren't too huge. Obama admits to making a couple grand on AVI. But that would make him one of the lucky ones. This chart shows you how AVI stock fared after the bird-flu mania ran its course.

So it's poetic justice that Obama lost a much bigger pile of money on the second of the lousy stocks, Skyterra Communications (OTC BB: SKYT.OB), which had a hot story about its plans for hybrid satellite/terrestrial communications. Apparently, no one remembers the lesson of Iridium: It's tough to compete with giants like T-Mobile, Vodafone (NYSE:VOD), and AT&T (NYSE:T) when the only differentiator is the promise of communications from places no one wants to be anyway.

It should surprise no one, then, that Obama's satellite stock, a perennial, money-burning loser, has been mauled in the market, despite having been pumped (with the prediction of a triple) by one Tejas Securities. Which leads us down another freaky rabbit hole. Tejas is a subsidiary of yet another bulletin-board-listed company, one that has shed about three-fourths of its stock price over the past two years and posted losses of nearly $50 million for the trailing 12 months ended in September 2006.

And according to that Times article, the chair of Tejas, and affiliates, donated $150,000 to Obama's political committees, in addition to arranging for his use of private planes.

If you're familiar with Illinois politics, none of this will surprise you. (If you're not, John Kass will give you a crash course.) Tidy connections between pols and biz figures are the rule there, not the exception.

The moral of the story? Faces may change, but the story sounds the same.

Oh, and don't bother taking stock tips from Obama or his broker.

Comments? Bring them here.

At the time of publication, Seth Jayson had no positions in any company mentioned here. See his latest blog commentary here. View his stock holdings and Fool profile here. Vodafone is a Motley Fool Inside Value recommendation. AT&T is a former Stock Advisor pick. Fool rules are here

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