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The September 2008 bankruptcy of Lehman Brothers was the largest in U.S. history. In 2007, Lehman achieved record earnings. What happened? Who is to blame?

Caesars Entertainment was a large casino operator in the United States that had been purchased in a 2008 leveraged buyout by Apollo and TPG. In January, 2015, Caesars Entertainment Operating Company (CEOC), its largest subsidiary, filed for Chapter 11. This set up a battle between the company and a set of large distressed investors. At issue was not only how to restructure the business and reduce Caesars debt, but also multiple lawsuits alleging that the company had damaged creditors in their quest to preserve equity value. Of particularly focus were a series of transactions that took place during 2013 and 2014 to sell assets from one subsidiary to another and to eliminate a valuable parent guarantee that had been granted to CEOC creditors. This case provides a good example of a variety of "defensive maneuvers" employed by companies and their private equity sponsors to protect a troubled investment.

Spreadsheet supplement for case 214084.

Spreadsheet supplement for case 215070.

The June 2013 bankruptcy of the city of Detroit, Michigan was, at the time, the largest municipal bankruptcy in American history. Detroit had struggled for years with a weakening tax base, high unemployment, a heavy debt load and increasing retiree costs. These financial strains led to cuts in basic public services, declines in population, and significant urban blight. The State of Michigan appointed an Emergency Manager, Kevyn Orr, to lead the city though the restructuring process. In March 2014 Kevin Orr and his team put forth a restructuring plan to the city's creditors that provides for needed reinvestment in City services, but low recoveries for unsecured creditors. The city's plan also proposes that a collection in the Detroit Institute of Art be transferred to a trust funded by philanthropists, with the proceeds accruing solely to retirees, rather than to all creditors. Kevyn Orr and his team must now find consensus on a plan that meets the needs of the city and is acceptable to its creditors.

Set in 2013, School Specialty was a financially troubled supplier of educational products to primary and secondary schools in the United States. The company planned to file Chapter 11 in order to address its excessive debt load, but needed to arrange debtor-in-possession financing to provide liquidity while in bankruptcy. The company has received a financing proposal from its existing term loan lender that includes some aggressive and unusual features. This includes the requirement that, immediately upon filing for Chapter 11, School Specialty undertake to sell its assets under Section 363 of the U.S. Bankruptcy Code. The Company must decide whether to accept this proposal, and what other options may be available.

This case examines the issues of establishing a capital structure for the leveraged buyout of Harrah's Casino.

Bain Capital had purchased Outback Steakhouse in 2007 and despite the myriad initiatives to improve operations, the financial collapse in 2008 threatened the company's ability to meet its loan covenants. Outback's performance steadily declined throughout the year. How should Bain Capital manage the company's debt while improving Outback's performance?