Rocking gently on the protected waters of the Chicago Harbor on Lake Michigan, the guests aboard Charles Bidwill’s luxury yacht sipped cocktails and savored a gourmet dinner on that fateful night in 1932. Never mind that Prohibition was still in effect, and it was the darkest depths of the Great Depression. Life was good for the Windy City’s most “charmingly flamboyant promoter and sportsman,” as the Chicago Tribune once dubbed Bidwill. Which is certainly a very Chicago way to describe Al Capone’s former business associate, who’d made a fortune in dog and horse racetracks, and was now part-owner of the Chicago Bears football team.

But at least one of Bidwill’s guests that night was feeling the pinch of the shattered economy, a local doctor who also owned a team in the fledgling National Football League. Named the Chicago Cardinals, the team now known as the Arizona Cardinals had always played second fiddle to the town’s beloved Bears, and was nearly $1 million in debt in today’s dollars. So the doctor made the famously competitive Bidwill an offer he couldn’t refuse.

As Bidwill’s grandson and current team owner, Michael Bidwill, explained to The Arizona Republic in 2018, “After a few drinks, the then-owner of the Cardinals was complaining about how much money he was losing. And my grandmother said, ‘Well, sell it to Charley.’ As I understand it, we purchased it for $5,000 – $2,000 cash right there on the boat, which was a lot of money in the Depression. My dad told me there was $45,000 of debt on the team at the time. It was recorded as a $50,000 sale.”

Not too shabby for a team now valued at more than $2.5 billion. But here’s the craziest part of the long, convoluted history of America’s oldest professional football team. It turns out that for the Cardinals, being bought by on a whim by an alleged bootlegger and notorious gambler like Charley Bidwill, isn’t even the craziest chapter.

Established in 1898 on Chicago’s South Side, the Cardinals were originally known as the Morgan Athletic Club, until a contractor named Chris O’Brien took over and moved the team to nearby Normal Field. Reflecting their new home field, the team played as the Normals for several years. But after O’Brien bought second-hand, faded jerseys from the University of Chicago (aka the Maroons), which he shamelessly rebranded as Cardinal red, they were once again rebranded – and they’ve been known as the Cardinals ever since.

Meanwhile, Bidwill was building a diverse if sometimes extra-legal business portfolio. Born into a politically connected family on Chicago’s west side, he earned a law degree and fought in World War I, before becoming head of a firm that printed racetrack programs and betting tickets. Famed for his “love for action” the Tribune writes Bidwill also “brought prize fights and six-day bicycle races to the city,” as the operational head of Chicago Stadium, a then-cutting-edge, 20,000-seat indoor arena. Half a century later, Michael Jordan’s Chicago Bulls would defeat Charles Barkley’s Phoenix Suns inside this now-demolished stadium on their way to their third consecutive NBA title.

But it was Bidwill’s involvement with an infamous horse racing track called Sportsman’s Park that would land him in hot water with the NFL, and his wife in the crosshairs of a U.S. Senate investigation into organized crime. Famously founded by Al Capone, less well known is that, “Charles Bidwill, future NFL Hall of Famer, was a major stockholder [at Sportsman’s Park], writes Tracy Thibeau of the Professional Football Researchers Association.

After Capone was sentenced to prison for tax evasion, Sportsman’s Park was ‘sold’ to Capone’s lawyer, Edward “Fast Eddie” O’Hare. (If that name sounds familiar, it’s because O’Hare’s son would go on to be a WWII flying ace and the namesake for O’Hare International Airport.) But just five days before Capone was released from Alcatraz, even Fast Eddie couldn’t escape a pair of armed assassins, who chased him as he drove home from the racetrack before blasting his car with shotguns. “Having all the characteristics of a Capone syndicate execution,” O’Hare’s 1939 murder was never solved, but when his estate was settled, the Tribune revealed he had a yacht in Massachusetts, a north side “hideout” apartment, “and was a director of the Chicago Cardinals.”

“The revelation that O’Hare owned stock in the Cardinals shocked NFL President Carl Storck,” Thibeau writes. “He said that league records did not indicate that O’Hare was a franchise director and launched an investigation. Bidwill went on to say that O’Hare had acquired his stock from a previous owner who had since retired from pro football.”

That same year, Bidwill was “indicted in federal court along with James M. Ragen and others in connection with his printing company supplying racetrack information to [bookies],” the Tribune reported. Who’s James Ragen? Well, for one, he co-founded the Morgan Athletic Club. Yes, the same club where the Arizona Cardinals first started as a scrappy amateur squad in the city’s rough and tumble Back of the Yards neighborhood.

Bidwill’s indictment was eventually dismissed, and in 1946 he bought Capone’s old horseracing track outright – but only after the previous owner reported to the FBI that he’d received a threatening note with a bullet inside, and then an armed gunman broke into his home. Sadly, just one year later, Bidwill died of pneumonia at the age of 51. His widow, Violet, was named the new owner of the Cardinals, and the treasurer at Sportsman’s Park.

“I don’t think people know it, but my grandmother was the first female sports team owner, and she ran the team for 15 years,” Michael Bidwill told The Arizona Republic. Not that Violet completely avoided the spotlight. In 1950, she made headlines when Sportsman’s Park was named in the U.S. Senate’s Kefauver investigation, a series of televised hearings that first exposed Americans to the national organized crime syndicate network known as the Mob or Mafia. According to the Tribune, “the track’s auditor testified that he had lent $80,000 of the track’s funds to Paul ‘The Waiter’ Ricca, the reputed mobster with power to influence the awarding of racing dates.”

But Violet Bidwill also accomplished one of the few things her husband couldn’t. In 1948, just one year after his death, the Chicago Cardinals won the team’s second, and still most recent, NFL championship. Nonetheless, the team was not long for the Windy City. Faced with flagging ticket sales and bankruptcy, the Bidwills moved the franchise to St. Louis following the 1959 season.

Had he lived to witness the long-awaited championship, Charley would have undoubtedly been thrilled. After all, football was never about the bottom line for this racetrack raconteur – he had other, more dependable ways of making money. Reminded that he lost more than $500,000 on the team through his career, Charley was quoted by the Tribune as saying: “What the hell. What good is that dough if you can’t have fun with it?”