New York City Multifamily Podcast

Episode 61: Navigating Chaos & Leveraging Bankruptcy Tools with Leo Jacobs


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Shaun Riney and Seth Glasser sit down with Leo Jacobs, a nationally recognized restructuring and business litigation attorney. Leo breaks down what the landmark Pinnacle portfolio bankruptcy auction really means for rent-regulated assets and the broader market.

Drawing on his deep experience mediating between borrowers and lenders, Leo explains why bankruptcy isn’t a dirty word—it’s a strategic tool to right-size debt, buy time, and reset capital stacks when traditional negotiating fails. He digs into:

  • Why the Mamdani administration’s attempt to condition the Pinnacle sale around repairs was unlikely under federal law
  • How lenders and owners rethink leverage when values fall and debt overwhelms assets
  • The psychological and tactical realities of navigating distress, including when to restructure, when to walk away, and how to work with lenders during volatile markets

This episode gives investors and operators a grounded look at the changing landscape of multifamily distress and how to make sense of it with clarity and strategy.

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New York City Multifamily PodcastBy Joe Koicim, Shaun Riney, and Seth Glasser

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