In this season finale of The Octus Download, hosts Jason Sanjana and Kevin Eckhardt are joined by the Honorable Michael B. Kaplan, U.S. Bankruptcy Judge for the District of New Jersey, for a candid look at how bankruptcy actually works from inside the courtroom. After settling the long-running debate over whether Central Jersey exists (00:03:54), Judge Kaplan explains how judges evaluate feasibility in modern Chapter 11 cases (00:05:03), addresses criticism around “Chapter 22” filings like Rite Aid (00:09:44), and discusses why courts are often reluctant to reject aggressive DIP financing outright (00:26:33). He also weighs in on bankruptcy venue, breaking down how companies choose where to file, why multiple jurisdictions are often legally valid, and why judges hesitate to second-guess venue decisions that comply with the statute (00:15:20), before sharing his frustrations with form-driven legal practice and public criticism of the judiciary (00:25:40, 00:37:41).

The episode then shifts to Update Corner with a look at the growing squeeze in Las Vegas tourism, where luxury spending persists but falling visitor volumes and job losses point to deeper structural strain (00:42:25). From there, Jason and Kevin enter Conspiracy Corner to unpack the baffling price action in First Brands’ DIP financing, exploring why a supposedly senior, protected investment is trading at distressed levels and what that might signal about control, funding, or market dynamics (00:48:07, 00:54:55).

The season closes with a spoiler-filled breakdown of Landman’s bankruptcy subplot, including a captive insurance tax scheme and why bankruptcy makes for better television than simpler financial solutions (01:01:42), followed by a thank you to the team and a special nod to Producer Tanya for making the show happen all season (01:08:01)

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Hosted by Jason Sanjana & Kevin Eckhardt Guest: Judge Michael B. Kaplan (U.S. Bankruptcy Court for the District of New Jersey) Produced and Edited by Tanya Hubbard A Production of The Octus Podcast Network

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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

Jason Sanjana and Kevin Eckhardt open with Sonder’s spectacular implosion, where a Chapter 7 filing and a broken Marriott integration turned hotel stays into evacuation drills. At (02:45), they unpack why guests were kicked out mid stay, how the deal fell apart, and why travel bankruptcies always hit consumers the hardest.

At (12:07), they turn to Meta’s scam economy. Fake celebrity ads, counterfeit products, crypto traps, and a moderation system that quietly profits from the gray zone between “real” and “obviously fake.” Jason and Kevin break down how misinformation spreads, why victims blame themselves, and why Meta would rather price scams than block them.

The show shifts at (17:04) to the rise of fake news aggregators, including a phantom auto lender bankruptcy story that fooled half the internet. The hosts look at how recycled content and algorithmic boosts have made disinformation feel routine.

Trend Watch hits at (24:36) with the national coffee shop shakeout. Red Bay, Switchback, Cup of Austin, Compass Coffee, and others are sliding toward Chapter 11 as bean costs, climate shocks, tariffs, labor, and rent all spike. Even Starbucks is trimming. Demand isn’t gone. Margins are. At (29:04), this weeks Unofficial Sponsor: The Collective Hive, the only lifestyle brand that promises freedom from decision making by eliminating your ability to have any.

Culture Corner begins at (30:05) with Pluribus, the Apple TV series where a viral alien gift turns humanity into a blissed out hive mind. Everyone joins except Carol Sturckow, who still feels grief, irritation, and a very human urge to run. Jason and Kevin debate whether the hive is salvation or annihilation, and whether individuality is overrated anyway.

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Hosted by Jason Sanjana and Kevin Eckhardt Produced and Edited by Tanya Hubbard A Production of The Octus Podcast Network