Dive Brief:

• Sears Holdings' board has brought in investment bank Evercore to review past deals involving CEO Eddie Lampert, including the sales and spinoffs of the retailer's business units and real estate, according to a Reuters report. Lampert, together with the hedge fund he controls, ESL Investments, is a majority shareholder and a major lender to Sears.
• The company, which filed for Chapter 11 last week, did not respond to Retail Dive's request for comment. A spokesperson for ESL told Reuters that such "analyses are customary and ESL is confident that the subcommittee will confirm that the transactions involving ESL were on fair and reasonable terms and approved under appropriate corporate governance procedures."
• Lampert, meanwhile, is pursuing yet another deal with Sears as he tries to raise a bankruptcy financing package for the retailer. The Wall Street Journal reported Friday that the company has more time to lock down the financing after the retailer's performance exceeded internal forecasts. CNBC reported Thursday that Lampert is trying to win added protections for his interests in negotiations with banks around the debtor-in-possession (DIP) financing.

Dive Insight:

Prediction: Sears' board won't be the only stakeholder group looking into the retailer's deals with its CEO. Especially for unsecured creditors, investigations and litigation around past ownership decisions is a primary way to gain leverage and repayment in the bankruptcy process.

Lampert has long played multiple roles around Sears, as chief executive, majority owner and a major creditor — roles that don't always align nicely in the real world. They could also affect the outcome of the retailer's bankruptcy. Lampert through his hedge fund has loaned Sears hundreds of millions, and he's also bought up other pieces of the company's debt, which gives him far more leverage than other shareholders.

Philip Emma, a retail analyst with Debtwire, estimated that, based on Sears 10-Ks, Lampert and other insiders own more than $2.4 billion of funded debt across various agreements. Emma also pointed out in an interview earlier this month that Lampert — along with being an owner, manager and creditor to Sears — is a landlord (through a real estate spinoff he co-owns) and a supplier (through his stake in Lands' End).

As for Lampert's push to get more DIP financing to the retailer, the extra time bought this week could prove crucial as it moves into the holidays. (The company also just won court approval to start closing an initial round of stores, according to court documents.)

In court papers last week, attorneys for Sears noted how important the $300 million in junior financing Lampert is working on would be. Initially, they said the financing would be necessary for Sears to continue operating beyond the first two weeks after bankruptcy. That's because, just to keep the lights on, Sears has been burning through more than $100 million in cash. For now, though, according to the Journal, the retailer has some much-needed breathing room.

Along with providing DIP financing, Lampert is also a contender to buy the retailer once it pares down in Chapter 11. That depends on a lot of things, including how the company performs over the next two months or so. According to Sears' DIP terms, it needs to have a baseline or stalking horse bidder lined up by Dec. 15.