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On Tuesday, I wrote a post downplaying the recent insider buying in Sears (SHLD) by CEO Eddie Lampert and Bruce Berkowitz's Fairholme Capital. In it, I argued that Lampert and Berkowitz would be looking after their own interests--which they will--and that for that reason, investors would be best off by not reading too much into the insider buying.

After writing that post, I heard from Barry Kupferberg, Director of Research at Trilogy Capital Management, who explained why the insider buying might mean something after all.

1) Most of the debt is secured: Sears has about $4 billion in debt, and about three-quarters of that is secured. That means the debt won't disappear upon a bankruptcy filing, but will be covered by asset sales or collateral. Further more, Some $1.6 billion of that secured debt is owed to Lampert, but as an insider, it may be treated like equity, Kupferberg says. "At a minimum, he’ll have a fierce legal challenge and have to battle it immediately," he says. And bankruptcy can be very, very expensive.

2) Fraudulent Conveyance Rules: Sears transferred properties to Seritage less than two years ago, and if Sears filed for bankruptcy now, "fraudulent conveyance" could be alleged. What's fraudulent conveyance? It's the argument that if Sears went bankrupt within two years of transferring the properties, then it was probably insolvent already and may not have received fair value for its asset transfers. That's something Lampert will want to avoid as the outcome can be highly uncertain, Kupferberg says.

3) Lampert's Ownership Stake: Lampert already owns more than 50% of the stock, so what's another 1%? "There’s nothing in buying more stock that would help him to gain more control," Kupferberg says. "All he’s doing is spending good money." That must mean he thinks it's cheap, Kupferberg says.

4) Short Squeeze: There are 17.6 million shares of Sears short, according to Bloomberg, and only 24 million shares that aren't "stagnant." If a short seller needs to cover, Kupferberg says, "there’s nobody to buy the stock from."

5) No More Bad News: In the past few weeks, Sears has announced terrible fourth quarter earnings, and acknowledged that its "historical operating results indicate substantial doubt exists related to the Company’s ability to continue as a going concern," in its most recent 10-K. "A good argument can be made that all the bad news is out," Kupferberg says.

The upshot: "Right now, it’s very likely he doesn’t file, and likely he continues to support Sears in a meaningful way," Kupferberg says.

Put it all together, and Sears could have more upside. But I still wouldn't chase it.

Shares of Sears have gained 3.3% to $11.88 at 9:59 a.m. today.

Correction: In an earlier version we incorrectly attributed the "going concern" comment. It was made by Sears in its 10-K, not its auditors.