Ralph told me stories of visiting Hot Springs, Arkansas, with Al for rest and relaxation. The resorts there were classified as a safe haven, no matter whose side you were on. Ralph talked about how it was entirely possible to find himself sitting in a hot bath with the FBI director. This was also the place where he and Al could meet with the leaders of rival gangs and share information—anything from where to buy the best goods at the best prices to where to find girls for a short holiday.
Obviously, in Al and Ralph’s line of work, beautiful women were not hard to come by. With all the money and influence they had, and all the time they spent away from home, they were bound to attract admirers—and they didn’t do much to discourage them. My uncle Bites dated a woman named Loraine, whom everyone called Larry. She told me that during that period, the woman Ralph was seeing, and later married, Valma Pheasant, said to her, “Better spend their money first because they’ll just piss it away, anyway!”
Gossip columns about Al and Ralph’s exploits with women—complete with photographic evidence—started appearing in the papers. And, of course, my father, Sonny, and Aunt Mae saw those articles. It was not easy for them to take. There were murmurings in the family about how Aunt Mae once said to Sonny, “Your father broke my heart, please don’t you break it also.”
Al’s penchant for pleasure wasn’t limited to women, though. He was a connoisseur of good music, and the height of his wealth happily coincided with the explosion of jazz music on the American cultural scene. Chicago was the center of the jazz craze, and both Al and Ralph were the biggest jazz impresarios in the city. All the best jazz musicians wanted to play their clubs.
When Louis Armstrong was playing with his wife Lil Hardin’s band at the Dreamland Café in 1925, my grandfather Ralph heard him perform. They got to talking, and Louis told him about the famous Cotton Club in Harlem and how it provided opportunities for black musicians. That club, incidentally, was owned and run by Owney Madden, a prominent bootlegger and gangster. Louis’s stories planted a seed in Ralph’s mind, and pretty soon, he was running one of the grandest nightclubs of the day in Cicero, a little joint he called the
Cotton Club.
It was there that he and Al gave black musicians like Earl “Fatha” Hines, Duke Ellington, Cab Calloway, Jellyroll Morton, and Fats Waller their professional starts. Very few people know that it was my grandfather Ralph who “discovered” Ethel Waters. Ralph once took me to night club named
The Chez Paree
in Chicago to see Nat King Cole sing and play the piano. After his set, he came over to our table, and right away, I could see that he and my grandfather knew each other well. He invited us to come backstage to show us around.
When I asked Ralph how he knew Nat King Cole, he said, “Oh, he used to play in our nightclubs when he was still in high school. He wasn’t known for his singing in those days, but man could he play piano. We got along OK, but he really loved Al.”
Life was difficult and dangerous for black musicians in Chicago in the 20s. Many club owners were known to extort money from their black performers, but Al protected the entertainers who worked for him. He even supplied some with bodyguards when it was necessary.
As Ralph explained to me, “Al really liked the blacks; he appreciated their music more than I did. To me it was just a business. As long as they showed up, kept their noses clean, and the customers liked them, they had no problem with me. But if they screwed up, they were out on their ass. Al was more lenient, so we had some arguments about who was gonna stay and who was gonna go. Usually Al won. Sometimes Al would throw a private party and Fats or the King would play all night, and after every couple songs, Al would stuff a hundred dollar bill in his pocket.
Al would tell me ‘Ralph, these poor bastards are going through the same kind of crap that us Italians had to put up with a generation ago. Even worse! So I’m glad to help them make a living, especially when they are as talented as these guys are.’”
In a 1931 article in
Harpers Monthly
, Katherine Fullerton Gerould called Al Capone “one of the central figures of our time.” In a way, he represented a way of life. Of course, part of his legendary stature involves the mystique of crime, but he also stands out as a figure who championed central elements of American culture when they were first emerging in the 20s, most notably jazz, and the freedom and individuality that went along with it.
As Gerould puts it, “Capone was a Ford or a Rockefeller with a shoulder holster. He flatly broke laws his public either wanted broken or cared little about, yet hadn’t the nerve or resources to break themselves, and he might personally knock an officious lawmaker down the stairs. He killed or had killed only those that the public, had they dared, would have happily dispatched of themselves.
It is not because Capone is different that he takes the imagination: it is because he is so gorgeously and typically American.”
Chicago, 1926 – 1929
Let the worthy citizens of Chicago get their liquor the best way they can. I’m sick of the job. It’s a thankless one and full of grief.
- Al Capone
As the 20s drew to a close, Al began to see the writing on the wall. Prohibition was probably the most despised law ever enacted in the United States, and the most ignored. By 1930, there were more than 10,000 illegal drinking establishments in Chicago alone. All of the largest and most prominent of these—and the majority of the smaller ones, too—were controlled by Uncle Al. He was generating more than $100 million a year in income, all of it in cash.
But he could sense the impending end of Prohibition, so he actively looked for ways to get into another business—a legitimate business. Like Michael Corleone in
The Godfather
, Al desperately wanted to funnel his cash into building a more secure life for himself and his family.
My grandfather Ralph told me about the emotional toll Al’s dangerous lifestyle was taking on him. To both Al and Ralph, there were two sacred rules for living. First, family is everything. And second, your word is your bond. So when they started to see the viciousness that was proliferating among the Chicago gangs, and the willingness many gangsters had to backstab, renege on their word, and even threaten the families of other gangsters, they wanted out.
And in addition to fearing for his family, Al feared for his own life. His wife, Aunt Mae, once told me, “I don’t know if you knew this, Deirdre, but your uncle Al had bad dreams almost every night. He would wake up and the bed sheets would be soaked with sweat. I’d have to change the sheets in the middle of the night.
One recurring nightmare was about the time in 1926 when he was having lunch with Frankie Rio at the Hawthorne Inn and seven cars pulled up and fired thousands of machine gun bullets into the restaurant. When it actually happened, he came out without a scratch, but in his dream he was riddled with bullets. He was burning with pain and bleeding all over.”
Mae believed that Al had a gift of prophecy, and that his dreams foretold events before they happened. To her, and to Al too, that was how he managed to escape the many dangers that perpetually dogged him. But there was one recurring dream that both he and Mae hated, and that Al couldn’t shake. In this dream, he watched the police pull bodies from the Chicago River—the bodies of Mae and Sonny. He was terrified this dream would come true, and it was one of the reasons he bought a house in Florida—so that Mae and Sonny could live away from Chicago. It was also a major reason he was so eager to find a way out of the Outfit.
Ralph remembered Al going on long rants about the madness of running the Outfit. He could quote these rants from memory: “I’ve got to get out, Ralph. I’ve got enough money. I don’t need this insanity. Weiss, Moran, and those other assholes are idiots. [Hymie Weiss and Bugsy Moran were members of the Outfit’s rival gang, the North Side gang] You can’t do business with crazy people. I’ve been shot at, almost poisoned with prussic acid, and there is an offer of $50,000 to any gunman who can kill me. They don’t understand that there’s enough for all of us. They don’t have to cut in on my territory. What do they expect me to do, let them get away with it? They agree to something, then they break the deal. They’re pissed because I run a better business. I make more money than they do. They are jealous bastards. They want what I have. You can’t trust ’em. Their word doesn’t mean shit. I run my outfit like a business. It is a business.”
Al would often follow these rants by drifting into a list of his big ideas for leaving the Outfit. He had a number of different plans for what he could do with his life in the legitimate world. One idea was to get one of his writer friends, like Ben Hecht (who would write the screenplay for Gone with the Wind in 1939) or Damon Runyon (who wrote the musical Guys and Dolls), to help him write his autobiography.
Runyon was a particularly close buddy to both Al and Ralph. He loved Theresa’s cooking and was often a guest at the Prairie Avenue home when he visited Chicago. Many of his stories and characters are based on his relationship with my uncle and grandfather. Al hoped that if Runyon helped him write a decent book, it could be made into a movie, in which he would play himself. He said he wouldn’t have to be a great actor—he’d just be himself. And he would invite performers like Louis Armstrong and Duke Ellington to play in scenes shot at the Cotton Club.
Runyon and Hecht both shared interest in the idea. But when Al approached them about the project, neither could find time within their schedules. Barely a few years later, he was convicted of income tax evasion and sent to prison—and so the book never happened.
Another idea Al bandied around was to release a line of designer clothing. In Chicago in the 20s, Al was a fashion plate. He dressed impeccably in custom tailored suits, coats, hats, shirts, and ties—and he always chose the finest, imported materials. Men all over Chicago copied his “look,” and so eventually a well-known clothing designer approached Al about creating the “Al Capone Collection.”
At first, Al kind of liked the idea. Clothing is certainly a “legit” business, and he thought he could make enough money with the line to get out of the rackets completely. But he was also concerned that getting into fashion would detract from his tough image. He understood that no matter how much he distanced himself from the Outfit, he might always be under threat—and so becoming a fashion icon didn’t seem like the safest new identity to take on.
Al turned his keen businessman’s eye to less conspicuous businesses—and happened upon the dairy industry. As he put it himself, “You gotta have a product that everybody needs every day. We don’t have it in booze. Except for the lushes, most people only buy a couple of fifths of gin or Scotch when they’re having a party. The working man laps up half a dozen bottles of beer on Saturday night, and that’s it for the week.
But with milk! Every family, every day, wants it on the table. The people on Lake Shore Drive want thick cream in their coffee. The big families out back of the yards have to buy a couple of gallons of fresh milk every day for the kids. Do you guys know there’s a bigger markup in fresh milk than there is in alcohol? Honest to God, we’ve been in the wrong racket right along.”
Al and Ralph already had access to bottling facilities for their bootlegging business, so it wasn’t hard for them to add milk to their slate of products. My grandfather Ralph is credited with being the first to date-stamp milk bottles. Though most people think he got his nickname “Bottles” from being a bootlegger, it actually came from his clever idea about putting the date on milk bottles so that people at the grocery store would know how fresh the product was.
But selling milk and other soft beverages never quite took off in the same way selling liquor had. And Al wasn’t ready to trade in his high-rolling lifestyle for the more tame life of a milkman. He enjoyed being a big shot and courting the limelight—so much so that he often went so far as to hold press conferences. What other big time racketeer had both the panache—and the courage—to do that?
Al understood that his celebrity status put him in a unique position to help people. He didn’t want to lose that leverage. Not only was he committed to the performers and musicians who worked for him, he also wanted to have the social clout needed to step in where others—even law enforcement—often fell short. For example, he volunteered all of his resources to aid in the search for the kidnapped Lindberg baby.
“A kidnapper is no better than a rat,” Al said, “and I don’t approve of his racket because it makes the kidnapped man’s wife and kiddies worry so much. I shall be glad to help Chicago in this emergency.” The police, unfortunately, did not take him up on his offer. Maybe the outcome would have been different if they had.
So, Al kept searching for ways to quit the Outfit without completely relinquishing his position of power. He eventually stumbled on the idea of purchasing the Edgewater Beach Hotel, north of the loop on the shore of Lake Michigan. He thought it was the classiest hotel in Chicago, and he was going to make the penthouse suite his summer residence. Then he would redesign the hotel nightclub and book all his favorite entertainers.