It’s day three of my annual Tales of the Cocktail awards odyssey. It starts out like the previous two days: walking around the convention’s Ritz-Carlton headquarters, sampling this and that, and running into familiar industry folks. The first familiar face I see is Paul Hletko, founder of FEW Spirits from the Chicago suburb of Evansville, a trusted industry source, and a passionate fan of the NHL’s Chicago Blackhawks.

“You hear that Rocky died yesterday?” he says after obligatory pleasantries. I nod in the affirmative.

This brief exchange carries a Schroedinger’s cat type of vibe: It’s not related to the booze industry, but it is. The Rocky in question is Rocky Wirtz, who became the Blackhawks’ owner in 2007 after his father Bill passed away. He simultaneously assumed control of the other family business: Wirtz Beverage Group, a liquor distribution company founded in 1946 by his grandfather and former Blackhawks owner Arthur Wirtz. Two industries shaped by the same family empire lost the same guy.

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This bridge between liquor and sports ownership among the “Big Four” sports leagues (the NFL, NBA, MLB, and NHL) is not historically unique. View these instances over the course of history, and they chronicle the sports landscape’s rise from casual pastime to serious business. They also reveal that, off the field, sports can get kind of weird.

How Booze Owners Shaped Baseball

The first professional baseball game occurred in 1869, and booze barons got involved shortly thereafter and rescued the sport from fading away. The American Association, an upstart league with strong ties to the alcohol industry, formed in 1882 and revived waning interest in pro baseball by offering beer and Sunday games. The rival, more puritanical National League disdainfully nicknamed its competitors “the Beer and Whiskey League.” Not that the American Association’s team owners cared. Most of them were brewery, distillery, or saloon owners, and their interest wasn’t necessarily inspired by a deep love for the game. German-American entrepreneur Chris Von Der Ahe — essentially the George Steinbrenner of his day, except more likable — initially purchased a stake in the St. Louis Browns (now known as the St. Louis Cardinals) after realizing how much local baseball games boosted sales in his saloon.

Fast-forward to the early 20th century: Baseball was well-established as the national pastime, and the New York Yankees were perennial American League losers. Enter Jacob Ruppert, former U.S. congressman and owner of Jacob Ruppert Brewing. He purchased the team in 1915, engineered a trade for Babe Ruth, and funded the building of Yankee Stadium in 1923. Under his ownership, the Yankees transformed into the empire that people either love or hate to this day.

The alcohol industry would continue to influence the business of baseball from the owners’ box over the next several decades. When Anheuser-Busch purchased the St. Louis Cardinals in 1953, it became the first publicly traded entity to own a team. Brewery president August “Gussie” Busch ran the club as president and intended to change the Cardinals’ stadium name from Sportsman’s Park to Budweiser Stadium — a revolutionary move at the time. The National League rejected this maneuver, claiming the moniker might encourage underage drinking. Busch complied and renamed the field Busch Stadium, but he’d have the last laugh: In 1955, Anheuser-Busch launched a new beer named Busch Bavarian.

The same year Anheuser-Busch got involved with baseball in St. Louis, Jerold Hoffberger used beer as leverage to move a franchise out of the city. Hoffberger was president of the Baltimore-based National Brewing Company, a family business best known for producing Colt 45 and National Bohemian (a.k.a. “Natty Boh”). He was part of a syndicate that purchased the St. Louis Browns (a different franchise than Von Der Ahe’s 19th century club), with the intent of moving the team to Baltimore. One problem: Washington Senators owner Clark Griffith protested, stating a Baltimore franchise would encroach on his market. Hoffberger smoothed over this roadblock by allowing Natty Boh to sponsor the Senators. Griffith agreed, the move occurred, and the Baltimore Orioles hit the diamond in 1954.

Alcohol also helped fuel baseball’s expansion into Canada. Charles Bronfman, former co-chair of the Canadian liquor conglomerate Seagram’s, served as majority owner of the Montreal Expos when they entered Major League Baseball in 1969. In 1977, a consortium led by Labatt Breweries landed the winning bid to own the Toronto Blue Jays as an expansion team, one year after the brewery’s failed attempt to purchase the San Francisco Giants and move them to Toronto. Even if Labatt’s lost the bid, the liquor industry might have won regardless: One of the losing bids came from a group led by Hiram Walker and Sons executive Lorne Duguid.

More Balls, More Booze

The liquor industry wasn’t solely fixed on baseball. It mostly steered clear of football, but it  managed to make waves during its brief forays. James Busch Orthwein, the great-great-grandson of Anheuser-Busch’s Adolphus Busch and member of the brewery’s board of directors, purchased the New England Patriots in 1992 when the team was terrible and attendance was abysmal. He acquired the team with an endgame in mind: Move them to the Busch family’s home turf of St. Louis after the1993 season. His plans were thwarted by Robert Kraft, who used his ownership of the Patriots’ home field, Foxboro Stadium, as leverage to compel Orthwein to sell the team to him.

While football team ownership remained sparse, alcohol companies staked significant claims into basketball and hockey. Seagram’s first step into sports happened in 1923, five years before it became a public company. It purchased a primary sponsorship stake in a semi-pro basketball club in Rochester, N.Y. It promptly branded them the Rochester Seagrams, with the brand name emblazoned on the front of the jersey in appropriate font. (Yes, they did have the occasional player who wore No. 7). This wasn’t as narcissistic as it may sound; back then, semi-pro basketball teams typically bore their sponsorship group as their nickname. Such a partnership may appear contextually scandalous since it started during Prohibition, but there’s no evidence of any moral outrage. Seagram’s parted ways with the team in 1945. The club would eventually change its name to the Rochester Royals, join the NBA, and become the Sacramento Kings several decades later.

Canadian alcohol companies particularly demonstrated an obvious love for hockey. This passion helped to forge a history that’s entangled and somewhat messy, with Molson central to the biggest knots. In 1957, brothers Harland and Thomas Molson used the profits from their family’s brewing empire to acquire the Montreal Canadiens. They held onto the team until 1971, when they sold it to Edward and Peter Bronfman of the Seagram’s empire. The Bronfman brothers ran the club from 1972 to 1978 before selling the club back to the Molson family. The Molsons went on to sell roughly 80 percent of the team to American businessman George Gillet Jr. in 2001, only to buy it back from him in 2009.

The Canadiens also maintained a fierce and occasionally bloody provincial rivalry with the Quebec Nordiques during the Molsons’ second reign. While infamous moments like the Good Friday Massacre define the on-ice feud, the bad blood bubbled before the two teams ever played each other. In 1976, Canadian brewery and Molson competitor Carling O’Keefe became majority owner of the Nordiques when they were part of the World Hockey Association (WHA). On March 8, 1979, with the WHA on life support, the NHL proposed to absorb the Nordiques and three other teams (including the Edmonton Oilers and Winnipeg Jets) pending a league vote. The Molson-owned Canadiens initially vetoed the move, a decision that put the lives of the four WHA teams in peril. Word got out, and boycotts and violent threats ensued — first in Quebec City, Winnipeg, and Edmonton, then across Canada. These actions compelled the Canadian House of Commons to urge the NHL to vote again. They did. The Canadiens, wary of the boycott, changed their vote. The Nordiques would join the NHL, and Carling O’Keefe would remain its owner until 1989, when it had to sell off the team — due to the brewery’s merger with Molson.

Good, But Not Flawless

Despite all this messiness, the alcohol industry actually is pretty darn good at sports ownership. The Yankees won six Series titles under Ruppert’s control. The Cardinals took home three World Series trophies under Anheuser Busch’s watch. The Canadiens hauled in 13 Stanley Cups with Molson at the helm, and four more under Seagram’s just for good measure.

That’s not to say these titans of the alcohol industry aren’t faultless. This ultimately brings us back to the Wirtz family. Arthur Wirtz helped purchase the nearly bankrupt Blackhawks in 1946, the year after his eponymous Wirtz Corporation expanded from real estate into booze. His real estate holdings included arenas like Madison Square Garden and St. Louis Arena, and he’d leverage the latter to compel the NHL league to expand to St. Louis in 1967. The Blackhawks enjoyed a mini-dynasty under Rocky Wirtz’s leadership, winning three Stanley Cups in six years: 2010, 2013, and 2015.

These good deeds exist under dark clouds. Bill Wirtz’s tendency to run the Blackhawks as cheaply as possible during his ownership period earned him the derisive nickname “Dollar Bill,” and his refusal to show home games on local Chicago television nearly obliterated local interest in the team. Rocky Wirtz resolved a lot of his father’s sins — the Hawks were back on local TV within a year of him taking over the team — but plenty of obituaries noted Rocky was owner during the Kyle Beach sexual assault scandal that occurred in the midst of the team’s 2010 Stanley Cup run. For a longtime Blackhawks fan like Hletko, these darker moments are important to acknowledge.

“Being a fan is not about painting with a rosy brush. There can be a dirty undercurrent that contains all sorts of nastiness,” he explains. “Overall, [Wirtz family] ownership has been fantastic, and their impact on hockey and the Chicago community has been so massive. But there have been black eyes.”

Big Leagues, Big Money

Sports ownership is an exclusive club, and it seems tonier than ever. The average team value across the Big Four was roughly $2.6 billion in 2022. Such a price tag can deter a person or company attached to the alcohol industry from owning a team, but it’s not impossible. Winery mogul Bill Foley entered the sports arena as majority owner of the expansion team Vegas Golden Knights when they hit the ice in 2017. They’re currently the reigning Stanley Cup champion. The possibility of achieving this level of success may tempt another alcohol-related entity to bite the bullet and snap up a franchise. After all, bottles and brands may disappear, but flags fly forever.