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Three bootlegging, bookmaking brothers are remembered in a new book

The Washington Post logo The Washington Post 12/1/2020 John Kelly

To the FBI, Charles “Rags” Warring was a bootlegger and a numbers runner. To the IRS, he was a tax cheat who had the audacity to claim as deductions the bribes he paid to District cops. To The Washington Post, he was the “genial triggerman” of a Washington gang.

To Leo Warring, he was Dad.

“They used various labels, like ‘mobster,’ ” Leo said of the way his father was described in print and in the courtroom. “I don’t relate to them at all. I would say that’s not the case.”

Triggerman?

“I think it’s a little bit of an exaggeration,” said Leo. “He was involved in some shootings, admittedly. But he was a very outgoing, personable, likable person.”

Of course, you can’t choose your parents. And you definitely can’t influence the lives they led before you were born. But you can tell their stories, which is what Leo has done with his book, “The Foggy Bottom Gang: The Story of the Warring Brothers of Washington, D.C.” (Parafine Press).

Charles Warring was born in 1907, the youngest of Bruce and Julia Warring’s 10 children. The elder Warring ran a cooperage in Georgetown. He expected his children to take over the family business, but lifting heavy barrels held no appeal to Charles and two of his brothers, Emmitt and Leo.

“Not when it was a lot easier and more profitable to get into bootlegging,” said Leo. “It was too much to keep them at the barrel shop.”

Prohibition did not magically reduce the demand for intoxicating beverages. It simply drove the liquor business underground. The three Warring brothers were happy to help. When Prohibition ended, there was still a market for untaxed liquor, which the Warrings provided.

Soon they got into the numbers game, running an underground lottery that reportedly took in $2 million a year. They frequented a Foggy Bottom bar called Pete Dailey’s, part of a D.C. demimonde that included such figures as Sam “Pickle King” Beard, Victor “Toots” Juliano and Alfred “Puddinhead” Jones.

And the nickname “Rags”? It came from how messy even the nicest suit looked on Charles, especially compared with his natty brother Emmitt, recognized as the brains of the operation. (It was strictly the press who used the moniker. “No one in the family called him Rags,” said Leo.)

Rags was involved in at least two shootings, one fatal. That was on Nov. 7, 1933, at a U Street nightspot called the Wunder Bar. Joseph “Gyp” Nalley was part of a rival gang that was, Leo said, much more violent than the Foggy Bottom boys. Somehow, Rags and his friends wound up at a table near Nalley and his friends. The result was three slugs from a .32 in Nalley’s chest.

Witnesses told police they came from Rags’s gun, but when it came time for the formal inquest, people clammed up. Rags was never charged.

Rags spent time in prison for other transgressions, including nearly three years for the same thing that got Al Capone: evading taxes on his ill-gotten gains. The Warrings kept meticulous records of their bookmaking operation, apparently believing that if they were ever caught, they could simply pay the appropriate taxes. That didn’t fly with the IRS.

By the time Leo came of age, Rags was mostly out of the business, though he did teach his son how to tell if your car was being tailed.

And Leo said his father never expected him or his brother to follow in his footsteps.

“Because my father only got a sixth-grade education, he was very big on education,” he said. “He stressed it a lot to us. When I was in college in Kentucky, I made the dean’s list two or three times. I can still see the smile on his face when I showed him my report card.”

In his old age, Charles “Rags” Warring went to Mass every day. He was remembered as someone who, back when he was flush, supported local charities. He died in 1969.

His son went on to a 40-year career at the Treasury Department. Now 72 and retired, Leo lives in Harwood, Md., in Anne Arundel County. He started research for the book after his son Charles came across his namesake grandfather in a 1954 court case. With newspaper archives easily searchable online, Leo began exploring how his family was once depicted.

“They’ve kind of risen almost to the surface and can be dug up by hand,” he said. “If somebody was going to dig them up and present them to the public, I wanted to be that person.”

Not everyone is appreciative: “I’m getting some blowback from some relatives who think I should have left them buried.”

Leo said he tried not to cast the Foggy Bottom Gang as saints. He makes a distinction between “criminals” and “bad guys.” There’s no denying that his father and his uncles were criminals. But they weren’t bad guys.

“Maybe I’m biased,” I said, “but I don’t see them that way.”

Twitter: @johnkelly

For previous columns, visit washingtonpost.com/john-kelly.

a group of people posing for a photo: Brothers Charles "Rags" Warring, left, and Emmitt Warring ran bootlegging and bookmaking operations in Washington in the 1930s and '40s. A new book by Charles's son Leo Warring -- "The Foggy Bottom Gang" -- tells their story. © Evening Star Collection/D.C. Public Library Brothers Charles "Rags" Warring, left, and Emmitt Warring ran bootlegging and bookmaking operations in Washington in the 1930s and '40s. A new book by Charles's son Leo Warring -- "The Foggy Bottom Gang" -- tells their story. a couple of people that are standing in front of a building: Leo Warring, left, with his son Charles and grandson Winston. In his new book, "The Foggy Bottom Gang," Leo tells the story of his father and uncles, who ran bootlegging and bookmaking operations in Washington in the 1930s and 1940s. © Kathy Warring Leo Warring, left, with his son Charles and grandson Winston. In his new book, "The Foggy Bottom Gang," Leo tells the story of his father and uncles, who ran bootlegging and bookmaking operations in Washington in the 1930s and 1940s.
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