Loophole City: The Secret History of Nashville’s Tall and Skinnies

Michael DiLucchio

Loophole City is a three-part narrative about the secret history behind Nashville’s tall & skinnies, how a legal loophole reshaped whole neighborhoods, and what we might build after the loopholes close. From I-40’s cut through Jefferson Street to a condo law turned tall-and-skinny machine, we trace how Nashville learned to game its own rules—and what it might take to finally rewrite them.

Episodes

  1. JAN 20

    The Missing Rung | Ep 3

    In the final episode of Loophole City, we stop looking backward—and ask the only question that matters now: What can Nashville build next? For decades, Nashville’s growth has been shaped by a loophole: two big homes on one lot, over and over again. But between the single-family house and the downtown tower, there’s a missing rung on the housing ladder—triplexes, fourplexes, cottage courts, and other “house-scale” buildings that add more front doors without changing the feel of a street. To figure out what it would take to build that middle on purpose, we follow three case studies from places that went first: Prairie Queen (Nebraska): a full neighborhood built almost entirely out of missing-middle housing—designed to look like houses, but quietly hold multiple homes. Portland (Oregon): what happens when a city legalizes the middle rung in existing neighborhoods—and tracks what actually gets built. Sacramento (California): a brand-new approach that rewards form over unit counts, and tries to shift the math toward more smaller homes. Then we come home to Nashville: what Metro passed on December 4, 2025, what RN/RL and DADUs actually change, and why the stretch between now and April 2026 is the pivot point—when new zoning becomes lines on a map, and lines on a map become politics on your block. This isn’t an episode about “build everything” or “build nothing.”It’s about directing development—so the city stops growing by loophole, and starts growing by design. Because the next chapter of Nashville isn’t just being written by developers or planners. It’s being written by whoever shows up. For more info go to: loopholecitypod.com

    39 min

  2. JAN 13

    The Machine | Ep 2

    Nashville’s tall-and-skinnies didn’t arrive because someone “planned” them. They arrived because the system rewarded a blueprint: find the loophole, file the paperwork, build through it. Episode 2 The Workaround traces the rise of the HPR loophole—from the 1963 Horizontal Property Act (written for condos), to the 1990 tweaks that made it easier to “turn the key,” to the 2001 Attorney General opinion that officially declared HPRs are not subdivisions—meaning the biggest chokepoint for public pushback and cost could be bypassed. Then the economics catch up. COMZO’s zoning legacy keeps Nashville neighborhoods low-density, but downtown demand flips when a mayor bets on an arena and changes what it means to live in the core. With legal keys in hand and demand in the market, developers begin iterating—neighborhood by neighborhood—until the HPR becomes the dominant unit type reshaping Nashville’s infill development This episode follows the timeline. Ultimately discovering what we gained, what we lost, and why the loophole that was once “affordable” drifted into something else entirely. For more info visit: loopholecitypod.com

    28 min
  3. The Blueprint | Ep 1

    JAN 13

    The Blueprint | Ep 1

    Nashville didn’t become a tall-and-skinny machine by accident. It became one by learning a strategy: read the rules, exploit the loophole, move on. Episode 1, “The Blueprint,” takes you to the beginning—when the incentives of federal highway funding made it cheaper to destroy than to build renewal. You’ll hear how the route for I-40 shifted north into Jefferson Street, how the state “technically” complied with public input, and how Metro consolidation changed the political math the moment the highway plan was ready to move. At the center is Edwin Mitchell—and a warning that proved prophetic. Because the story of Nashville’s growth isn’t just about what was built. It’s about what the system rewarded. This is Loophole City: The Secret History of Nashville's Tall and Skinnies For more information about the project, visit: loopholecitypod.com

    24 min

  4. JAN 7

    Loophole City: Trailer

    Look around Nashville right now and you’ll see them everywhere: tall, narrow houses—side-by-side—squeezed onto lots that used to hold one brick ranch. Locals call them “tall and skinnies.” Loophole City is a narrative series about the hidden legal loophole that reshaped whole neighborhoods—and the fight over what Nashville builds next. We’ll go back to the 1960s, when a highway and a handful of planning workarounds drew the blueprint. Then we’ll follow the developers who used it to fuel one of the largest infill booms in the country. And finally, we’ll break down the choices Nashville faces today—and what could come after the tall-and-skinny era. By the end, you’ll know why your street looks the way it does—and what it could look like 10 years from now. Website: https://loopholecitypod.com

    1 min

Trailer

About

Loophole City is a three-part narrative about the secret history behind Nashville’s tall & skinnies, how a legal loophole reshaped whole neighborhoods, and what we might build after the loopholes close. From I-40’s cut through Jefferson Street to a condo law turned tall-and-skinny machine, we trace how Nashville learned to game its own rules—and what it might take to finally rewrite them.

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