10 Famous Sites & Hangouts From Detroit’s Dark Past

The past is always present in the future, but sometimes the past can easily be disguised. Take Detroit for example, a city that has a dark and violent history that isn’t always present to the eye today. The truth is that some of the iconic landmarks around the fourth-largest city in the Midwest hold secrets from the past, hidden behind some of these forgotten sites and hangouts.

Most notable is the Purple Gang, a group of bootleggers led by Abe Bernstein in the 1920s who used extreme and excessive violence during the Roaring Twenties, which ultimately caused the gang to disperse in the 1930s. We now take you back on a virtual tour of Detroit, starting with a trip to Grosse Pointe Park, an affluent city in Wayne County.

1. Middlesex Road

Two houses stir up interest here. The first is 701 Middlesex Road, once owned by a top Detroit Partnership enforcer, whilst his neighbour across the boulevard at 702 was owned by none other than underboss Tony Zerilli — the son of long-time mob boss Joe Zerilli, who ran the syndicate from 1936 to 1977.

The interesting fact about these two houses is they are connected by tunnels that run across the street, and both had many James Bond-styled quirks — from peepholes in the doors designed for gun barrels to fit through, a basement entrance protected by an iron gate and even an empty space not recorded on the blueprints, situated behind one of the closets.

2. The Book-Cadillac Hotel

Back in 1924, when Sam Catalanotte was at power in Detroit’s underworld, the Book-Cadillac Hotel opened its doors and immediately held the title for Detroit’s tallest building — and the tallest building in the world at the time.

It soon became the main Purple Gang HQ, seeing many meetings over the years, and became Abe Bernstein’s permanent residence until he passed away in 1968. Abe lived in a suite on the top floor. The hotel fell into disrepair for decades but was fully restored and reopened as a Westin hotel — one of the few Detroit mob locations still standing and entirely recognisable today.

3. Hotel La Salle

Jerry Buckley was a 39-year-old radio commentator who also worked as an investigator for Henry Ford and as a special investigator for the government. In 1930 he campaigned for the recall of Mayor Charles Bowles in the wake of corruption allegations. The campaign was successful — and the following morning, Buckley was approached by three men and shot eleven times in the lobby of the LaSalle Hotel.

It later emerged that the murder had more to do with underworld blackmailing than politics. Detroit Police Commissioner Thomas C. Wilcox declared that Buckley was a known extortionist and racketeer. The case was never solved.

4. Doherty Hotel

In May 1938, the Doherty Hotel became the scene of one of its most dramatic moments. Central Michigan oil promoter Carl Jack Livingston — also a Purple Gang associate — got into a dispute about real estate with his cousin and lawyer Isaiah Leebove. Livingston was also worried that Leebove was closely aligned with Meyer Lansky and Arnold Rothstein, who had allegedly put a contract on his life.

Purple Gang enforcer Sam Burnstein was present at the table in the Doherty Hotel restaurant where Leebove and his wife were eating when Livingston came in and shot and killed his cousin. Livingston was found not guilty by reason of temporary insanity.

5. Vernor Highway Fish Market

After the death of Sam Catalanotte in 1930 from pneumonia, the Detroit underworld split into two factions. The West Side was controlled by Chester La Mare, whilst the East Side was led by Black Bill Tocco, Joe Zerilli and Angelo Meli.

On the afternoon of May 31, 1930, Gaspare Milazzo was sent by Sal Maranzano from New York to make peace between the two factions. Milazzo and his bodyguard, East Side soldier Sam Parrino, went to the fish market at 2739 East Vernor Highway. West Side hitmen ambushed them and opened fire. La Mare was behind the attacks — but he himself would be killed months later in retaliation.

The fish market, located behind the old Michigan Central Station, is long gone. It was roughly diagonal from what is now the 555 Gallery — a former police precinct.

6. Collingwood Manor Apartments

In mid-September 1931, three Chicago gunmen were killed in what became known as the Collingwood Manor Massacre. The hit was ordered by Detroit’s Purple Gang after the Chicago men had broken their trust.

Ray Bernstein — one of the founders of the Purple Gang and brother to Abe Bernstein — had bought an apartment at 1740 Collingwood Avenue and arranged a meeting that was in fact an ambush. The backstory: the three men had been given an ultimatum by Al Capone after extorting one of his speakeasies — either flee Chicago permanently or end up in a Chicago Overcoat. They fled to Detroit. In Detroit they tried to overpower the Purple Gang. Bad choice.

Ray Bernstein used Sol Levine as an unwitting accomplice, a mutual friend who watched the events unfold. The convictions that followed began the Purple Gang’s slow collapse. The Collingwood Manor Apartments still stand today.

7. Detroit Italian Bakery

Underboss Tony Zerilli owned a number of establishments throughout Detroit, using the Detroit Italian Bakery as his chosen headquarters. He also owned the Pasta Palace, which was tied to the famous “French Connection” — they were importing gallon cans of pasta sauce with kilos of heroin concealed inside. It remains one of the more extraordinary concealment methods in American organised crime history.

8. Eastern Market

The area known as Eastern Market in Detroit has plenty of mob history, some dating back over 100 years to the Adamo brothers who set up headquarters in the area. More recently, Vivio’s Bar & Grill and The Roma Cafe became hotspots of Detroit Partnership activity. In recent years Jackie the Kid Giacalone’s inauguration ceremony was held in Eastern Market.

Former Detroit enforcer Alan Lindbloom stated: “My grandfather, Peter Tocco, had his headquarters in the Eastern Market, which was, and still is to this day, mob central.”

9. The Hazel Park Horse Track

The Hazel Park Horse Track may be the most iconic contemporary Mafia location in the city — ground zero for mob activity and staked out by federal agents for decades. Back in 1949, Tony Zerilli became president of the Hazel Park Racing Association and over the following two decades netted an estimated $15,000,000 a year in revenue.

Former enforcer Alan Lindbloom also recalled: “When I was arrested, they showed me dozens of videos and pictures they had taken of me coming and going from it. I once delivered $1.7 million there to the boss after a Super Bowl.”

In 1972, Tony sold up and invested his profits into the Spaghetti Palace restaurant near the Macomb Mall.

10. Wolverine Golf Club

The Wolverine Golf Club may have looked like your normal run-of-the-mill golf club, but in 1980 notorious bookmaker and underworld associate Jack Anthony Lucido acquired a share for $65,000 — bringing it into Detroit Partnership orbit for the first time.

Over the following decade the club’s growth drew federal investigators who believed mob boss Jack Tocco was behind the investment. An 82-count indictment was handed down in March 1992 charging crimes ranging from running an illegal gambling business to conspiracy to intimidate and extort. All 82 counts were eventually dropped — no one was convicted.

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