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His health rapidly declining, Capone lived out his last days in Miami with his wife. In response to the public outcry over the St. Valentine’s Day Massacre, President Herbert Hoover ordered the federal government to step up its efforts to get Capone on income-tax evasion. The Supreme Court had ruled in 1927 that income gained on illegal activities was taxable, which gave the government a strong case for prosecuting Capone. On June 5, 1931 the U.S. government finally indicted Capone on 22 counts of income-tax evasion. Obviously, it didn't work but they were determined to make his stay in Miami as uncomfortable as possible. The City of Miami called his home "a menace to the safety and well-being of residents" and the State of Florida declared martial law and ordered the immediate arrest of Capone.
Tax evasion
While Capone ruled Chicago, Benjamin "Bugsy" Siegel ruled New York, and then later moved on to L.A. Siegel created an empire of bootlegging and gambling, and began one of the first organized hit companies "Murder, Inc." before he settled in Los Angeles. In L.A., Siegel rubbed shoulders with the celebrity elite, even dating a few starlets, as he also planned to expand a gambling empire in Las Vegas. Many mobsters, however, chose to live their daily lives rather anonymously in homes more fit for the family man than the big "boss." He returned to the Miami house after prison, and spent the rest of his life there.
Al Capone's homes were fit for a kingpin
Furthermore, to accommodate outside investors, Miami authorities liberalized rules for dog and horse racing, so naturally, northerners came to sultry, sweaty Miami to partake in profitable, illegal business endeavors. The two-story stucco house is awash in white -- topped with white terra-cotta roof tiles (which were probably originally red), and accented with white awnings. Inside, the renovation of the first floor is mostly complete, while upstairs is still gutted. A large, covered loggia on both sides of the living room flank the house, meant for natural cooling and cross-ventilation in pre-air conditioning days.
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He attained notoriety during the Prohibition era as the co-founder and boss of the Chicago Outfit. Developers also dredged the bay to create man-made residential islands extending off the causeways. With only one gated entry and exit to each island and heavy police security, homes were considered to be very secure. It remained in the Capone family’s possession until the mobster’s granddaughters sold some of the family’s treasures in 2021.
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I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze.
Its sponsor, the Republican state senator Bryan Avila, insisted the law was needed to hasten the removal of dangerous or worn-out buildings at risk of collapse, and was not intended to smooth a path for greedy developers. “Ocean Drive is not going to get bulldozed,” he told legislative colleagues in April. Original features such as a striking all-black art deco bathroom were refurbished, along with additions made by Capone after he bought the house for $40,000 in 1928.
Al Capone had more money than he had sense, which is really saying something since he was a criminal mastermind. He was able to use that dough to buy a palatial place in Miami, a massive mansion in New Jersey, and a comparatively modest brick two-flat in Chicago's Lincoln Park Manor neighborhood. Per the Inquirer, this humble Illinois home measured 2,820 square feet and had an apartment on each floor. Curbed Chicago writes that according to urban legend, the brick two-flat had a secret tunnel to his detached garage, but if it did exist, it no longer does. Our virtual tours uplift meetings and inspire connections for conferences, corporate groups, and universities.
Torrio hired Capone back in New York, and when Torrio moved to Chicago, he took Capone along and eventually handed the entire business over to Capone after surviving a drive-by shooting in front of his home on South Clyde Avenue. Al Capone's first home in Chicago was relatively modest for someone dealing in some pretty lucrative (but illegal) business. The mobster lived in the home when he first moved from New York to the Windy City. Capone lived in the Park Manor home until threats to run him out of town sent him to Florida. Despite rap sheets an arm's length and reputations for cruelty, there's something almost romantic about the gangsters of the 1920s. With a flair for the dramatic and personalities that dominated both the news and gossip columns, these men firmly put a mark on Prohibition history.
The gangster was convicted of tax evasion three years later and served seven and a half years in federal prison. I’ve told the story of these buildings countless times on our old walking tours. These days, if you want the full scoop, you can reach out to book a custom private tour. Al Capone has captured the interest of enthusiasts and historians for more than a century.
The sale comes only weeks after it was purchased by developers Todd Michael Glaser and his business partner Nelson Gonzalez in August for $10.75 million.
In 1920 during the height of Prohibition, Capone’s multi-million dollar Chicago operation in bootlegging, prostitution and gambling dominated the organized crime scene. Capone was responsible for many brutal acts of violence, mainly against other gangsters. The most famous of these was the St. Valentine’s Day Massacre in 1929, in which he ordered the assassination of seven rivals.
Unsurprisingly, the Stables was one of the hottest speakeasies in Al Capone’s Chicago. Star Island and Hibiscus Island are close neighbours, and all three islands are home to a number of high-profile celebrities, including Jennifer Lopez, Gloria Estefan, Don Johnson, Sean Combs, and Shaquille O'Neal. The home was the perfect place for the gangster's luxury hideaway. During the early development of Miami Beach, causeways – roads built on landfill and bridges – spanned the distance over Biscayne Bay from Miami to Miami Beach.
When Capone died, a New York Times headline trumpeted, “End of an Evil Dream.” Capone’s was at times both loved and hated by the media and the public. When Prohibition was repealed in 1933, some in the public felt that Capone’s and others’ involvement in selling liquor had been vindicated. But Capone was a ruthless gangster responsible for murdering or ordering the assassinations of scores of people, and his contemptible acts of violence remain at the center of his legacy. Capone’s image as a cold-blooded killer and quintessential mobster has lived on long beyond his death in the many films and books inspired by his life as the most notorious gangster in American history. Born in Brooklyn, New York in 1899, Al Capone moved to Chicago in 1919, where he made his mark as a bigtime bootlegger, per History. But between 1931 and 1934, he found himself going from house to house and state to state, each new one worse than the last.
I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. Chicago Detours is a boutique tour company passionate about connecting people to places and each other through the power of storytelling. We bring curious people to explore, learn and interact with Chicago’s history, architecture and culture through in-person private group tours, content production, and virtual tours. Second, Capone’s clients, henchmen, and opponents were primarily working-class and of immigrant stock.
Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours.
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