They say defeat is an orphan and victory has a hundred fathers. Likewise, the origin of many classic cocktails or iconic dishes is usually mired in pitched battles between generations of families, restaurateurs, and shady credit claimers. The Southside, a gin-based cocktail muddled with mint and citrus, and very popular among the South Hampton set, is one of those libations.

Thanks to Tobey Maloney, “chief intoxologist” and partner in Chicago’s Violet Hour cocktail lounge, this has been the summer of the Southside for me. While I was working on a story about Chicago bartenders who make their own cocktail bitters, Maloney shared his recipe for the Southside, and since then, I’ve been sucking ’em down like Rush Limbaugh working a Sizzler buffet. In addition to the refreshing taste, my verve for the drink was also borne of regional affiliation.

As a means of masking the swill, gang leader Frankie McErlane and his cohort, former bartender and wealthy bootlegger Joseph “Polack Joe” Saltis (ironically, he was born in Hungary), mixed it with lots of sugar and citrus—and thus the drink was born.

As I understood it, the cocktail was created out of pitched Prohibition-era Chicago gangland battles for superior spirits. The Northside gang led by Dion O’Banion had secured the good spirits pipeline, leaving only hooch and swill for the Irish Southside gangs, including the Saltis-McErlane gang, which was also affiliated with the more famous Johnny Torrio–Al Capone gang (later known as the Chicago Outfit). As a means of masking the swill, gang leader Frankie McErlane and his cohort, former bartender and wealthy bootlegger Joseph “Polack Joe” Saltis (ironically, he was born in Hungary), mixed it with lots of sugar and citrus—and thus the drink was born.

Whether or not this is true, it should be noted that McErlane had a violent streak that made Al Capone look like Martha Stewart. One of the era’s most notorious gunmen, he was the first gangster to use the “Tommy” gun and killed as many as 15 men during the bootlegging wars.

Just as I had mixed up another pitcher of Southsides and was gloating in the spoils of local mobster ingenuity, Eric Felten wrote a piece in last weekend’s Wall Street Journal, attempting to debunk the myth. As he writes:

There is no evidence that the Southside was ever served in Prohibition Chicago. And Saltis and McErlane focused on strong-arming saloons into selling their beer and their beer alone. Beyond such pesky details, the story makes no sense: Why would a drink from louche Chi-town speakeasies find its way east to be embraced by lock-jawed Locust Valleyites? One might just as well imagine the Astors inviting Big Jule over to shoot craps.

Felten also adds:

“… there is some doubt as to whether the Southside actually originated at the Sportsmen’s Club. But I find myself convinced. The men who fished and hunted at the Southside did their golfing, riding, and racquet sports at places such as the Rockaway Hunting Club, the Maidstone Club, and Piping Rock, which explains how the cocktail spread to become the definitive summer drink of the country-club set.”

While Felten provides circumstantial evidence to support his theory, he’s got no smoking gun, and thus his article proves to be mostly his opinion. Frankly, as a longtime Midwesterner, his column strikes me as run of the mill East Coast superiority and media bias. His strongest argument against the Chicago origin is that something born of a debauched poor place could never make its way into the rarified confines of the country club set. Yeah, and Joe Kennedy and Sam Giancana never, ever moved in the same circles. Likewise, rich people never eat lobster. (Lobster was once used as garden fertilizer and as a food staple for widows, orphans, servants, and prisoners. Massachusetts even passed a law forbidding its use more than twice a week, as a daily lobster dinner was considered cruel and unusual punishment.)

There’s been no direct chain of documentation produced to verify or deny these claims. What I do know is that it’s a damn good cocktail.

The 21 Club and a variety of other post-Prohibition era clubs also make a claim to the Southside’s birthright, and really, who the hell knows. There’s been no direct chain of documentation produced to verify or deny these claims. What I do know is that it’s a damn good cocktail. My version (below), based on experimentation with Maloney’s original, is different than Felten’s Journal recipe, which I find far too cloying. Part of the reason is that the recipe doesn’t employ cocktail bitters. That’s no surprise, as due to the popularity of vodka, which gets overpowered by the aromatic botanical nature of bitters, their use has waned even among classic bartenders. For gin and brown spirits, though, it’s a whole ‘nother game. Just as a chef tries to appeal to sweet, salty, bitter, sour, and umami in a dish, so should a bartender. In a drink like the Southside, bitters balance out the simple syrup, transforming a sugary confection into an aromatic and well-balanced gem. Cheers.

The Southside (aka, Upper Southside)

Definite origin: VanBuren and Green streets, Chicago. Tanqueray gin is a bit more medicinal than Sapphire for my personal taste but is a reasonable substitute. Likewise, try super-premium gins, à la Hendricks or, even better, North Shore Distillers for more Chicago flavor.

Regarding bitters, almost anyone can find Angostura (Peychauds has too much anise for this application), but I prefer Fee Brothers Old Fashioned, which has a spicier quality that melds well with the gin.

Ingredients

1. 1

    

   Put mint in bottom of a cocktail shaker and crush with the back of a spoon or muddler to release essential oils. Add about 5 or 6 ice cubes and remaining ingredients. Shake hard for about 10 seconds or until shaker frosts to the point where the cold stings your fingertips. Strain into a martini glass.