The city of New York enjoys recognition for its sweeping array of cocktails. Yet, the genesis of many of these admired beverages often traces back to unreliable beginnings. A classic case is the "New York Sour," a whiskey sour with flamboyant red wine flair. While its catchy name might suggest a Manhattan origin, historical diggings hint that perhaps it was Chicago that whipped up this drink first but merely chose a sloppy label.

Records suggest that what we know today as the 'New York Sour' was actually born in the heart of Chicago during the golden 1880s. The cocktail first surfaced as an innovative play on the beloved Whiskey Sour, but quickly ran into an identity crisis. Dubbed with multiple aliases, from the Continental Sour to the Brunswick Sour to the Claret Snap, the lack of a concrete designation only added to the scrumptious blend's historical puzzle.

Piecing together this cocktail conundrum, there is no tangible proof to claim Chicago as the corner where the New York Sour first sprouted. No recipe was shoved into a 19th-century drinks directory or hastily jotted down on a bar napkin. Nevertheless, archival evidence does show that a 'New York Sour-esque' drink was popular among Chicagoans long before it touched modern tongues on the East coast.

Released by the Chicago Tribune in November 1883, the 'Local Miscellany' column painted a picture of a local bartending maestro named Tommy, masterfully mixing a batch of in-demand indulgences. Offering insight, an interesting account of Tommy preparing a "pleasant-looking, red-haired drink," dubbed as a Whiskey Sour, can be found within this old saga.

“It’s far from conclusive that Tommy was crafting what we label today as the New York Sour," says The Apparatus Room's Lead Bartender Petr Balcarovsky. "Although it's referred to as a Whiskey Sour, the descriptive language employed hints closer to the Claret Snap, a similarly constructed cocktail with a red-wine float prevailing in that era."

A passionate cocktail history buff, Balcarovsky hinges on this small excerpt to dredge up the cobwebbed chronicles of New York Sour and sketch a likely timeline. While it doesn't hand over the invention credits to Tommy or even Chicago, it gently nudges its roots towards the windy city, much before the New York Sour emblazoned its maiden print appearance within the Boston Bartender's Guide in the year 1934.

Even so, the concoction's misleading moniker often leads aficionados astray about its actual birthplace. "I genuinely wish New York would embrace the shared background of the NY sour with Chicago," Balcarovsky candidly admits.

Regardless of its blurred genesis, the New York Sour continues to hold its own. This historical cocktail has seen a growth in popularity in recent years. The key to its continued attraction lies in its vivid contrast: the striking interplay between the dark red wine and the light brown spirit carries an aesthetic allure that's hard to resist. But the charm of the New York Sour goes beyond its good looks.

Katie McCourt, a veteran bartender at The Hoxton, Chicago, believes that the appeal of any drink ultimately marches back to its taste. Both McCourt and Barochovsky express a preference for robust, fruity wines such as Cabernet Sauvignon or Bordeaux blend for the layer of wine. Infusing rye instead of bourbon strikes a better harmony against the wine’s fruit-filled tunes, producing a sumptuous cocktail that transcends its enticing appearance.

While the exact cradle of the New York Sour may forever remain a debatable enigma, its enduring magnetism is far from being a mystery.