HIGH POINT CONFIDENTIAL: The cooperative bootlegger - 'Black Diamond' kept police busy in 1930s and '40s

Aug. 12—HIGH POINT — ou know you've achieved a lofty law-breaking status when you're more widely known by your nickname than your given name.

History is riddled with infamous bad guys — and bad gals — whose colorful nicknames overshadowed their real names: Jack the Ripper. The Zodiac Killer. The Hollywood Madam. Machine Gun Kelly. Blackbeard. Baby Face Nelson.

The list goes on and on.

In High Point, one such character was "Black Diamond," a notorious bootlegger whose nickname turned up in newspaper articles as early as 1915 but who made headlines much more frequently in the 1930s and '40s.

The curious thing about Black Diamond — well, one of the curious things — is that we're not sure what his given name was. The earliest articles refer to him as Henry Gilmore or Henry Gilliam, while later articles call him William Long.

Could this actually be two different people?

We doubt it. In both instances, Black Diamond was associated with a woman named Goldie — Gilmore, or Gilliam, ran around with a woman named Goldie McDonald, and Long was married to a woman named, well, Goldie Long. So two men — more specifically, two bootleggers — in the same city, having the exact same nickname, Black Diamond, and being in a relationship with a woman named Goldie? That's too much of a coincidence, don't you think?

So where did Black Diamond get his unusual nickname? We're not sure of that, either, but one High Point Enterprise article stated "it is believed to have come about as a result of a huge diamond he always wore on his finger."

What we are sure of is that this man — whatever his name was — was one of the most prolific bootleggers in town. During the 1930s and '40s, in particular, The Enterprise published numerous articles about Black Diamond and his various bootlegging exploits, but his reputation and his rap sheet can be traced back way before that. As early as 1916, an Enterprise article stated that Black Diamond "has been in court so many times that it would take an adding machine to count them up."

The earliest newspaper reference to Black Diamond seems to be in 1915, when he was alleged to have "knocked a ... woman in the head." In 1926, he was the subject of a catfight between two possessive women — the aforementioned Goldie and a woman known as "Sweet Mama Colleen" — and he ended up getting beaned with an electric iron one of them had thrown.

Mostly, though, Black Diamond made the paper for violating Prohibition laws.

In 1937, for example, a raid of his house on Kivett Drive turned up 58 pints of whiskey hidden beneath a mattress. After that, it seems, the raids on Black Diamond's house became so commonplace that he began simply inviting the officers inside and showing them where the whiskey was stashed.

Black Diamond was busted for bootlegging so often that the courtroom judges all knew who he was. One time, he told the judge he had resumed his illegal business because building contractors had accidentally ruined his vegetable garden, and he needed money to put food on the table. Another time, he said his uncle died, and he had stockpiled some whiskey to put in the coffee on the night of the wake.

"Black Diamond has been in court on liquor law violations so many times that the officers have lost count," The Enterprise reported in 1940.

In 1943, he was busted again and sentenced to a year in the federal penitentiary, but he still didn't learn his lesson. In September 1946, High Point police said they had raided the Kivett Drive house 13 times that year — and they found whiskey every time.

When Black Diamond died in February 1947, at age 65, police sentimentally described him as "High Point's most cooperative bootlegger," an unusual claim to fame for a man with a rap sheet as long as his, but a nice compliment nonetheless.

Even in death, Black Diamond wasn't quite done. In August 1948 — a year and a half after the notorious bootlegger died — police raided his house, now occupied by his sister-in-law, for the first time since his death.

Guess what they found.

jtomlin@hpenews.com — 336-888-3579