EP 21 | How Bankruptcy Really Works: Inside the System with Josh Sussberg

Jason Sanjana & Kevin Eckhardt open the episode from the Octus studio (00:00:06) and quickly bring in their guest, Josh Sussberg of Kirkland & Ellis (00:01:04). The conversation begins with Sussberg’s early ambition to become a sports journalist and his time at Syracuse University’s Newhouse School (00:01:55), before an almost accidental pivot into law. By (00:03:47), he explains how rotating through corporate, litigation, and real estate made it clear that bankruptcy was the only practice where the stakes were immediate, the decisions were real, and the work wasn’t just documenting outcomes already decided elsewhere.

From (00:05:40) through (00:07:58), Sussberg walks through how bankruptcy practice has evolved since the early 2000s. He explains how the 2005 amendments to the bankruptcy code compressed timelines, shortened exclusivity, and pushed negotiations earlier and largely outside the courtroom. Retail cases that once lingered for years are now decided at speed, reshaping how Chapter 11 actually functions.

The discussion then turns to defining retail bankruptcies of the last decade. At (00:08:53), Sussberg revisits Toys “R” Us, pushing back on the idea that it was a liquidation disguised as a restructuring and explaining how its complex capital structure distorted public understanding of the case. By (00:10:12), he describes how the filing itself became part of the problem. At (00:11:07), the focus shifts to courtroom strategy and first-day presentations, culminating in the story of Claire’s (00:14:08), a case widely expected to liquidate. He recounts how the company survived and why he ended up piercing his ear in court when it did (00:15:09).

Before exiting, Sussberg offers a blunt take on AI and legal practice (00:16:32). Tools may change, but responsibility does not. If it goes into a brief, he is still printing it, reading it, and owning it. He departs the episode at (00:17:32). Black Friday online sales hit a record $11.8 billion, but the hosts argue the headline masks weakness beneath the surface. Buy-now-pay-later usage surged more than 20 percent year over year (00:18:46), while in-store foot traffic continued its long decline (00:19:16), raising questions about whether installment-driven consumption reflects resilience or strain (00:20:03).

At (00:24:01) Miami Macy’s, makes its case, contrasting packed South Florida stores with a balance sheet propped up by flagship real estate. The episode closes with Kawhi Watch (00:26:00), where the Clippers’ 2–13 collapse during Kawhi Leonard’s injury absence mirrors unresolved questions around an alleged $28 million no-show endorsement deal tied to a bankrupt counterparty (00:26:46). As the hosts note, exposure doesn’t disappear just because the lights are bright. Paperwork has a long memory.----more----
Hosted by Jason Sanjana & Kevin Eckhardt
Guest: Josh Sussberg (Partner, Kirkland & Ellis)
Produced and Edited by Tanya Hubbard
A Production of The Octus Podcast Network