For nearly 90 years, the Downyflake wasn’t just a restaurant; it was the island’s economic and social equalizer. In a town increasingly defined by barriers, it was the one place where billionaires and landscapers sat at the same counter, united by a 90-cent doughnut.

 

It survived a gas explosion in 1991 and three different locations, but it could not survive the transition to the "New Downtown." Today, the property where the Downyflake once stood is a fenced-off foundation pit, a $10.75 million transformation of Nantucket’s mid-island corridor.

 

For Nantucket, this development is anything but ordinary. It is one of the largest private commercial structures ever permitted by the Planning Board, spanning 1.6 acres across from the Mid-Island Stop & Shop. Local headlines have focused on the mechanics: the three years of "hand-to-hand combat" between the Historic District Commission (HDC) and the Planning Board, and the $3.7 million in public funds authorized to keep Nantucket in "Safe Harbor" from unfriendly 40B developments.

 

The "Runaway Train" vs. The Regulatory Game

The road to approval was a masterclass in regulatory maneuvering. While some HDC members characterized the development as a "runaway train" that ignored the island's character, the developers played the long game.

 

It is a common tactic for sophisticated operators: submit a massive initial plan, wait for the inevitable local outcry, and then "compromise" down to the version they wanted all along. The final approved plan, two buildings totaling over 17,000 square feet of ground cover, is a scaled-back version of the original, yet it remains a massive footprint for the district.

 

But to accept this story as a simple win for local zoning is to miss the true scope of the players involved.

 

Follow the Money, Find the Players

The public narrative surrounding "New Downtown" is a sanitized, logistics-first account of a local need being met. A deeper story is not found in Planning Board minutes, but in corporate registries and regulatory filings in Manhattan and Boston.

 

This isn’t a story about a local builder trying to add a few year-round rentals. This is a collision between high-frequency, proprietary trading algorithms and Boston's "Hard Money" lending circle.

 

The faces of the project are Chris Fiumara and Daniel Najarian, co-founders of Boston-based Crowd Lending Inc. Publicly, they talk about "moving things on Sparks" and finding tenants. Their corporate bios paint another picture: Crowd Lending is not a bank. It is a hard-money lender that specializes in providing fast, high-interest, short-term capital to developers who need to bypass traditional bank red tape to close deals quickly.

 

Fiumara, in particular, has an extensive history of "hand-to-hand combat" in the Massachusetts court system. In partnership divorces (e.g., Fiumara v. Capobianco) and loan disputes (e.g., Fiumara v. Carpinteri), he has established a reputation as a fierce, sophisticated litigator who aggressively protects his investments. When a local contractor (like the Robert B. Our Co.) reportedly pulls out of the project, this "hard money" ethos, move fast, cut red tape, prioritize yield, is almost certainly the engine driving that friction.

 

The "Flash Boy" Connection

The deep capital, however, comes from a different universe. Property records confirm that Fiumara and Najarian’s partners include Jared Gerstenblatt and Christopher Grimaldi. These aren't developers. They are the managing partners of Chimera Securities, a proprietary trading firm based in Manhattan.

 

These aren't developers; they are "Flash Boy" era traders — a term popularized by author Michael Lewis to describe the elite quants who use speed and complex algorithms to find a market edge. To a quantitative trader, a project like Sparks Avenue functions much like a physical algorithm. They identify micro-advantages, such as SHI tax credits and public subsidies, to ensure the "trade" is profitable long before the first tenant moves in.

 

The true significance of the Sparks Avenue transformation lies in this data: it marks the precise moment mid-island shifts from a local community hub into a high-yield, diversified asset for New York quantitative portfolios.

Gerstenblatt and Grimaldi are experts in finding and exploiting fragmented value. For years, Nantucket’s mid-island corridor was "the locals' area," defined by year-round businesses and lower yields. That calculus has now, likely, permanently changed.

 

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More about 'The Players' here

 

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The Infrastructure Gamble

Beyond the ledgers, there is the physical reality of Sparks Avenue, already one of the island’s most congested arteries. To the developers, traffic is a variable to be managed; to the neighbors, it’s a permanent quality-of-life tax.

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During the multi-year approval process, the project’s traffic impact was a central point of friction. The developers provided studies suggesting that the "mixed-use" nature of the site would actually mitigate new trips, arguing that residents living above the restaurants would reduce the need for car travel. This "Level of Service" math is common in urban planning, but it feels theoretical on an island where the "New Downtown" sits directly across from the Mid-Island Stop & Shop's gridlock.

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The addition of an eight-lane bowling alley, a major destination asset, only deepens the skepticism. While the project includes 85 on-site parking spaces (eleven more than the town's zoning minimum), residents remain wary of the surge in evening and weekend volume.

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The Planning Board ultimately cleared the hurdle, attaching a condition that the developers contribute $10,000 toward island-wide bike and pedestrian improvements. In the world of Manhattan proprietary trading, a $10,000 mitigation fee is a rounding error, a nominal transaction cost to unlock a $10.7 million position. But for the year-round residents who navigate this corridor daily, it’s a small price for a project that will permanently change the flow of mid-island life.

The Public Subsidy Paradox

This context reshapes the conversation about the $3.7 million in public town funding.

 

Town leaders view this allocation as a victory — an efficient way to buy safety from predatory developments and secure eight affordable units. But when you look at the men holding the keys, the picture is more complex.

 

At a rate of nearly $462,500 per affordable unit in public subsidies, the Town of Nantucket is effectively providing low-cost infrastructure capital to some of the most sophisticated financial minds in the Northeast. Taxpayer-backed funds are being used to support a private arcade and an eight-lane bowling alley envisioned not by a community board, but by proprietary traders and hard-money lenders. These are specialists in distressed asset maneuvers and high-leverage financing who see the public grant not as "aid," but as a way to de-risk their investment.

 

The Downyflake may be gone, but its namesake site is now host to a far larger gamble. A group of New York and Boston capital specialists have taken a "position" on Sparks Avenue, and they have successfully moved the town to double down on their bet.

- Dominick Costanzo
Publication Lead

3/18/26