The Legend of Red Irving
Meet the Italian Immigrant from Yonkers whose life is shrouded in Lore and Legend
Published by Hudson Lore Society | June 1, 2022
The Man in the Red Shoes
Nestled along Midland Avenue in Yonkers, above a long-shuttered tailor's shop, sat a modest apartment that housed a peculiar man named Vincenzo Vespucci. While the year of his immigration to the U.S. is unclear, in his neighborhood he was known as a kind, Italian man with odd habits and generous hands. But to those who looked deeper - he was something far more complex.
They called him Red Irving. The nickname came from his near-daily walks along the Hudson River in Irvington, where he'd be seen puffing on a Montecristo Cigar and wearing a conspicuous pair of red tennis shoes. It was an eccentric signature for a man who otherwise seemed to live a modest life. The name stuck. He even began using it as a front for business dealings that were anything but legitimate.
Red Irving along the Hudson River - Irvington, NY (1931)
Blurry, but an unmistakable site: cigar smoke, red shoes (color enhanced),
and the wide Hudson.
The Operation
Red Irving didn't run a gambling racket or bootlegging ring like other enterprise titans of his era. His empire was built on liquid gold: olive oil. Through a web of customs controls, shipping diversions, and familial connections stretching from the Ionian Sea to the Bronx docks, Red smuggled hundreds of thousands of barrels of premium, Italian olive oil into the United States. By bypassing international tariffs and undercutting domestic brands, he quietly amassed a sizable fortune while hiding in plain sight. Some say his network was so well-oiled that even Prohibition-era smugglers sought his advice.
The Legacy
Between 1920 and the late 1930s, several well-funded civic projects appeared along the Hudson. Many of the financiers were listed as anonymous donators. But Irving was behind most of them -- laundering his growing fortune and building a covert distribution network. The Hudson River, poorly surveilled at the time, became his private highway. Boat houses, piers, and depots disguised as civic improvements were in fact routing stations for olive oil. Some connected to old rail lines which allowed Irving to move tons of product without ever passing through a port of inspection. Some say he secretly financed parts of the Bear Mountain Bridge. A brick on its west tower is allegedly etched with a red star-his private insignia.
Nearly Completed Bear Mountain Bridge - Cortlandt Manor, NY (1924)
The bridge's construction is credited to the Harrimans, a wealthy local family, who sold to the state many years later. It was believed Irving used his relationship with the Harriman Family to prompt and fund the project.
The Treasure
Of all the stories that swirl around Red Irving, perhaps the most intriguing is the one tied to his hidden world on Midland Avenue. Whispers suggest that somewhere within the walls and grounds of either his former office or one of the neighboring properties, he left clues to something deeply personal. But what exactly he hid remains unknown. Some call it a treasure. Others believe it was a confession. And some think it was his way of ensuring his story lived on - never fully told. Those who call the section of Midland Avenue 'home' often say the same thing about it: It feels like "something is waiting to be discovered."
Midland Ave. Apartment Door - Yonkers, NY (1937)
A blue entrance door (pictured in black & white) - the color ironically used by "Red" to identify his places of business.
The Disappearance
Following a fire at his Midland Avenue Office In 1956, Red Irving vanished. No obituary, funeral or trace. Some say he died alone in his hidden apartment. Others claim he boarded a train to Canada. A few believe he started over under another name, still wearing those red shoes. Whether fact, myth or legend, Irving's story continues to flow along the mighty Hudson River he once controlled; and his secrets, guarded by the tight-lipped neighborhood where his generous presence commanded utmost respect.
Montecristo Cigar Box recovered from the Midland Avenue Fire - Yonkers, NY (1956)
The box mysteriously disappeared from the evidence file - Along with Red Irving - shortly after the conclusion of the fire investigation.
Contribute a Story or Artifact
Have a Red Irving story or news?
Email us at info@legendofredirivng.com to add to the archive.