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July 3, 2025 17 mins

In this Retail Retold Replay, Chris Ressa dives into the winding path of a complex lease deal at a DLC shopping center in Cheektowaga, NY — where Five Below ultimately took the space, but not before a rollercoaster of negotiations, tenant terminations, and lessons in legal vs. physical possession.

The story starts with Office Depot downsizing, a prospective tenant backing out, and ends with a successful Five Below opening. Along the way, you'll hear why contingencies in commercial real estate deals are everything — and how timing, relationships, and flexibility can turn a near-miss into a win.

A must-listen for anyone in leasing, development, or deal-making.

Takeaways:

  • Buy now, pay later options are on the rise and appealing to younger consumers, and retailers are investing heavily in buy now, pay later platforms.
  • Supply chain challenges can vary based on ordering behaviors. Retailers who continued ordering during the pandemic are better positioned.
  • Five Below's entry into Cheektowaga, NY involved complex negotiations.
  • Possession in commercial real estate can be legally defined but physically contested.
  • The importance of having tenants who are committed to their locations.
  • Understanding the contingencies in real estate agreements is crucial.

Chapters

00:00 Introduction to Retail Retold

02:47 The Buy Now, Pay Later Craze

05:40 Supply Chain Insights

08:20 The Five Below Story

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