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Ann Adler, Pinkerton Agent
by Phil Angelo
She was not THE woman.
But she was certainly an extraordinary woman — and a damn fine-looking woman, too.
She was Ann Adler. Olive complexion. Copper-colored tresses. Green eyes like emeralds. Straight of shot. Memory like Morse Code.
She was tall for the times. Her figure was neither voluptuous nor vulgar, but, unlike her older sister Irene, no one could have ever mistaken her for a man. Willowy was the word. In Ann’s case, a bustle was slightly superfluous, unneeded really. Her shoulders were broad enough that the fake shoulder stuffing of the times was frippery.
Pistol or rifle, she was a marksman, make that markswoman. Annie Oakley may have been “Little Sure Shot.” Annie Alder could make you blush while hitting the bulls-eye.
There was the old bromide that God created man, but Samuel Colt made all men equal. Ann’s accuracy made her the equal of any man at any time.
Ann Adler was a Pinkerton agent.
She wasn’t the first female Detective Special Agent for the Pinkertons. That distinction belonged to Kate Warne. Kate had been alongside Abraham Lincoln, protecting him as his 1860 pre-inauguration train rolled along the Baltimore and Ohio railroad tracks toward Washington, where he was about to appeal to “the better angels of our nature” in his speech.
Now the bloody Civil War was over. The country, particularly the South, was struggling with its own form of avenging angels, or rather devils — the Ku Klux Klan.
The Pinkertons are remembered today for their postwar years as the protectors of scabs when the American Labor movement was in its infancy. If you ran a factory and a union was threatening, you called the Pinkertons. They would safeguard your machines. They would douse the fires of arson. And, yes, they would infiltrate unions, when needed.
That seemed repulsive then. It seems more so, now.
What was forgotten was that Allan Pinkerton was a firm abolitionist. He was a friend of and early contributor to John Brown, whose fire for freeing slaves would lead him to raid Harpers Ferry, Virginia, in 1859. Brown hoped to spur a slave rebellion. He utterly failed and wound up on the gallows. As he approached his death, he told the audience that the crime of slavery would only eventually be purged with blood. How right he was.
Now, in the post-Civil War years, the nation remained wrapped in violence. It wasn’t quite as organized as an all-out war, but the coffin, the rope, the fiery cross still meant death.
It was the time of the Ku Klux Klan.
The Klan has ebbed and flowed throughout American history. In the years after the Civil War, it grew rapidly. It spread and strengthened to intimidate the freed slaves from running for office, from serving on juries and even from voting.
The Pinkertons fought the Klan in the same way they fought the Confederacy. They were used to hiring and operating a network of spies. Allan Pinkerton was the OSS, the CIA, of his time. And he was absolutely unprejudiced. He would hire anyone who would get results: a stutterer; a man who masqueraded as an English Lord; double agents; and women. Women like Ann Adler and Kate Warne.
The Pinkertons, at a time when many others had given up in the fight for fairness, and equality for the freed slave, wormed their way into the Klan, breaking up the Kleagles, turning in the worst of the lawbreakers. It was a near hopeless task, like shoveling water upstream from a Niagara. It was the good fight, but a near hopeless one.
The country passed two Constitutional Amendments, the 14th and the 15th, to give African-Americans citizenship and the right to vote. They remained largely unenforced for three-quarters of a century. We should all believe in the importance of a law, but nothing is more futile in a democracy than a law that is ignored. President U.S. Grant pledged in his inaugural to uphold all the nation’s laws, even the unpopular ones. Under Grant, Northern troops policed and patrolled the South, enforcing the law and the hard-won rights of the freed slaves. The media, and the intellectual upper crust, more or less hounded Grant from office.
What we remember today of the Klan is a sort of an unfunny caricature. The Klan was lethal and cruel, and narrowminded. But it was also disorganized and unfocused. There were Klansmen who intimidated with the burning cross on the lawn. There were Klansmen known to stand next to the ballot box to see who was dropping their votes in. There were Klansmen who killed. Yet the rules and rituals varied from state to state and from town to town.
There was also an element of the Klan that was social, like it was a club that had gone wrong. You joined because everyone in your neighborhood or your county was already in. There were picnics and the passing of time. Like Watson writes of The Red Circle, it was murderous, but it wasn’t murderous everywhere, at every time, at every moment. It was also, at times, damn near impossible in some locations for a white to do business without Klan support, or at least without Klan sympathy.
The Klan, too, had a women’s auxiliary, always an influential idea. Auxiliaries were popular. The female arm of the Klan was a political powerhouse.
Adler wandered southward aboard the Central of Georgia railway and the Florida East Coast line. The Central of Georgia was one of the roads wrecked by Union General William Tecumseh’s bummers when they marched across the state in 1864. The northern soldiers set fires and tossed the rails on top, so they would soften. Then they were bent into “Sherman’s neckties.”
Her mission, ingratiate herself into Southern society and infiltrate the Klan. She was good at that. She was independent, well-read and well-educated. She could hold her own in any conversation from the serious to the recipes for tonight’s menu. The key was to be attractive enough to catch the attention of men, single or not, who would flirt. Yet she did not want to be a lightning rod for a jealous wife. Not easy. Spy vamps like Mata Hari are remembered. They are also quite dead.
Ann would pretend to be offended in some insignificant racial matter. That was relatively easy to do at a time when “Black man acting funny” was an offense. The world then was filled with “Sundown towns,” communities where a Black was not welcome in a public place once the sun set.
And in all cases, whether infiltrating a criminal organization, busting a union or trailing and tailing a bank robber, the Pinkertons were nothing if not dogged. As Butch Cassidy says to The Sundance Kid in a moment of exhaustion, “Who are those guys?”
Ann Adler rode south across Georgia. That was one of the deep South states. Out the window, she could still see the sections of the state burned out by Sherman. The cotton was gone. The ante-bellum mansions were cinders. The clay-like soil was exhausted, too. Scarlett O’Hara’s Tara was no more.
What remained, and what fueled the Klan, was bitterness. The white plantation caste in the South had lost just about everything in the war. The money was gone. Their financial power was gone. Their status was gone, too. The idea of equality with the Black man was simply anathema. The Klan was a way of striking back while evading the law behind a mask. There were an estimated 4,000 lynchings in the South. Most of those participating, according to the records we have, were never punished.
Lynchings were particularly risky to stop, because often, when officials were warned, they did nothing anyway. And an undercover agent always had to assess the risk of being “outed” by a leak of information.
Agents like Adler worked alone. Hers was shadowy work. There are no ceremonies for infiltrators, no medals, no citations, no public pats on the back.
Adler’s job was to find out who was underneath the Klan hood, and to sort out the membership, separating the offensive and intolerant from the killers marked for the hangman.
Infiltration is never an easy assignment. It takes months, even years, to gain the confidence of the Mafia, the Molly Maguires or the Klan. Only an organization with deep pockets, like the Pinkertons of their time, can do it. That’s true if the agent is James McParland and the Molly Maguires, Jack McMurdo and the Scowrers or Ann Adler and the Ku Klux Klan. Even then, the Pinkertons couldn’t afford to do it in every community or even every state. Some people, warned that the Klan was on their trail, would contribute. Some couldn’t afford to contribute.
The undercover work was not a “profit center” for the Pinkertons. It was an island of common decency.
But eventually it gets done, because if your criminal organization is based on intimidation, there is a tendency to brag. In this case, husbands told their wives. Their wives told Ann. Ann didn’t need any special uniform. There was no language barrier, though you had to get the accent right. It was a matter of listening to gossip as you kneaded the bread together or hid behind fluttering fans at a community cotillion. The key was to fit in, to seem like one of the group, while not leading the parade. It was a technique the Pinkertons taught and trained. It worked in the coal fields of Pennsylvania and the Confederate spy rings in Richmond and Baltimore. It worked here.
What was needed was a strong memory. So Ann would keep track of who was once important and who had suddenly left. She compiled names and professions. There was a lawyer who departed. Where did he go? What happened to that dry goods merchant? If a judge was intimidated, where did he go?
In 1876, the Klan hit one of its turning points. That was the year of the infamous Hayes-Tilden presidential election. Democrat Tilden won the popular vote. Three states, South Carolina, Louisiana and Florida, were in dispute. A special commission tallied all three for the Republican Rutherford B. Hayes, who became president. Hayes, in a compromise, withdrew federal troops from the South.
Reconstruction and all Black civil rights collapsed. The Klan was now less needed. The white supremacists who ran the Klan were now running the state governments. So if you had opposed the Klan, or had left the Klan in years gone past, it was time to go elsewhere geographically.
The carpetbaggers and scalawags now fled. Carpetbaggers were men from the North who came South to make fortunes in a rebuilding economy. Scalawags were Southerners who supported the new rights for African-Americans. When the troops left, the rights of the African-Americans left with them. The white supporters of African-Americans left quickly, too. Some went North. Those with the most smarts, like the Openshaws in “The Five Orange Pips,” left the country altogether.
But the Klan had a memory and it wanted to keep up intimidation as well as assassination. In Florida, the warning was the pips, seeds of an orange. In Louisiana it was an inch of sugar cane. In South Carolina, it was cotton seeds, torn from the boll by a gin.
Funded by the deep pockets of the Pinkertons, Adler stayed in the South when others left. As she learned who the pips were set on, she would travel the state, the South, the world, to pass on the warning.
Passing on the warning was as dangerous as gathering the inside information had been. Secrecy was vital. For an agent, to be seen, to be recognized, could be fatal. You had to work behind the curtain. If written about, as Watson might do, you had to work between the lines.
Consider the two cases where Holmes is hired to protect a client, but the client is killed anyway. Such is the fate of John Openshaw and Hilton Cubitt. The stories have startling similarities. Both start in America. Both involve shadowy communication, be it Dancing Men or papers on a sundial. Warnings had to be discreet.
Sometimes the beneficiary of inside information would flee again. In a different case, but with the same modus operandi, Jack Douglas blows off the head of vengeful Scowrer Teddy Baldwin in “The Valley of Fear.” A target could turn and fight.
Did you ever wonder why The Five Orange Pips made it into the canon? Why would Watson chronicle a case where Sherlock Holmes’ client gets killed? Why celebrate failure?
Because you are covering up your tracks. That’s why.
Because there were a dozen other unwritten cases where Holmes or Lestrade or Gregson was forewarned and intercepted the would-be assassins. There were many cases where Ann’s information saved a life, or punished a Klansman.
There is a passage from “The Valley of Fear” that is all too appropriate. The ending of the same novel is appropriate, too. It was a different infiltrator and a different group of racketeers — Birdy Edwards and the Scowrers.
“In vain,” The Valley of Fear says, “the money of the lodge — money squeezed by blackmail out of the whole countryside — was spent like water to save them.” The saving of them was to save them from the hangman’s hempen rope.
Yet as the story ends, the informer, Jack McMurdo, alias Birdy Edwards alias Jack Douglas, is pushed to his death into the ocean off a ship.
That’s the continuous challenge of an infiltrator like Ann — high reward, high risk. The agent risks their life every day, every hour, every minute. A single-slipped word, an intercepted letter, one minute of not noticing an unusual man in a crowd could mean death.
Agent Ann Adler saved countless lives, imprisoned dozens who society would not miss and is the silent inspiration behind the fifth story in “The Adventures of Sherlock Holmes.”
“The Five Orange Pips” started in Florida and ended up in Horsham, England. So did Ann Adler.
THE END
Travels with Sherlock 