As we head into the thick of the holiday season, most people are thinking about gift wrap and eggnog. But if you stand on the Windsor riverfront and look across to Detroit, you aren’t just looking at a view—you’re looking at the most consequential one-mile stretch of water in North American history.

A century ago, this was the epicenter of a global black market. Today, the frontline of a sophisticated trade war. It’s a story of how Windsor went from America’s bartender to its most formidable gatekeeper. We can call it The Big Flip.

America’s Dry Christmas

Picture this, it’s the Roaring Twenties. South of the border, the U.S. government is playing the ultimate buzzkill, banning booze nationwide. But here in Windsor? We were the neighborhood bartenders holding the keys to the cabinet.

Ontario law was clear: you could legally produce and warehouse alcohol—so long as it was for “export.” Detroit was the thirstiest city on the planet, and it was staring at us from across the river, licking its lips. The demand on their side was off the charts, but illegal; the supply on our side was also off the charts, but legal.

The result? The Windsor-Detroit Funnel. This wasn’t some leaky side hustle; it was the main artery of American Prohibition. Estimates from historians and Treasury agents are staggering: 75% of all illegal booze entering the U.S. flowed through right here. Forget the image of a few guys in rowboats; this was an industrial conveyor belt. The “Mosquito Fleet” of speedboats was so thick on the water that some nights you could practically walk across the river to Michigan.

Whiskey Sixes & the frozen Detroit River

When the temperature dropped and the river froze, the operation turned legendary. Welcome to “Rumrunner’s Christmas” on the frozen Detroit River.

In the dead of winter, the river transformed into a mile-wide highway of glittering ice. Our Santas drove “Whiskey Sixes”—souped-up Studebakers and Fords beefed up with six-cylinder engines to haul hundreds of cases of heavy rye whiskey from Canada to the USA. The runs happened at midnight. Engines roaring, headlights off – daytime running lights did not exist.

The first rule of Rumrunner’s Christmas? Never drive with the door shut. Not even at twenty below. You kept that door tied open because the Detroit River is a living, breathing thing. The current carves “pockets” under the ice. If you felt that sickening thud—if the nose of the Studebaker started to dip—you didn’t have time to fumble for a handle. You threw yourself out of the car and prayed – or found god.

Exporting “Sin City” to Vegas

The money didn’t just vanish; it was laundered into our city’s foundations: new buildings, community and religious institutions, houses, and the like; but we exported more than just Canadian Club whiskey—we exported the entire architecture of the modern underground economy.

Logistics, security, shadow-market management—it was all perfected here. Look at Moe Dalitz, one of the original rum-running kings who cut his teeth on the Detroit River. He took that expertise and used it to help build modern Las Vegas: Desert Inn, The Stardust, The Sundance Hotel, Las Vegas Convention Center, The city’s first private hospital, The first enclosed shopping mall in Nevada, Las Vegas Country Club, University of Nevada, Las Vegas, PGA’s Tournament of Champions, and the casino lounge concept itself! – all might not exist without Windsor whiskey.

We didn’t just keep America hydrated during Prohibition; we were basically silent co-founding partners of Sin City. These guys were the Silicon Valley entrepreneurs of their era. When they looked at a patch of empty Nevada desert, they saw opportunity, just like when looking at a frozen & empty Detroit River.

The Big Flip: From Outlaws to Gatekeepers

Here is the delicious, brutal irony of it all. A hundred years ago, the U.S. government was desperately trying to plug the bottle from the south side while we kept popping corks on the north. Fast-forward to today, and the roles have flipped.

American bourbon and winemakers are now the ones begging to ship north, and guess who’s holding the cork? Canada.

Between the LCBO and the SAQ, Canadian monopolies now control the gates. When the U.S. slapped tariffs on Canada, we didn’t just sit quiet—we froze U.S. liquor purchases. The result was a massive hit to their spirits industry: exports of U.S. spirits to Canada dropped roughly 75% practically overnight. In 1925, we were the “mosquitoes” buzzing around the American giant. Today, the LCBO is the giant. We’ve traded the “Whiskey Six” speedboats for boardroom chairs, but the border is still a funnel, and Windsor holds the cork.

The Ghost of Christmas Past Smiles Wryly

So this holiday season, as you’re hunting for that perfect bottle, spare a thought for the ghosts of Prohibition still haunting across the river, grinning at the irony of the wheel turning full circle.

If your favorite Kentucky bourbon is missing from the shelves, don’t just curse a generic supply chain—recognize the power of the gate we now control. Whether it’s a Whiskey Six racing across the ice or a trade deal signed in a boardroom, this remains the most storied one-mile of water in North America.

History proves that thirst always finds a way, and trade always finds a gap. And here in Windsor? We’ve always been the ones with the map.

Happy Holidays—and a word of advice from the old-timers: if you’re driving on the ice, keep your door tied open.