Chapter VIII

THE OLD MAN

We who worked under him were proud of his cold-bloodedness.

THE BIG KNOCKOVER (1924)*

Down the years, Hammett must have wondered what might have happened had he gone on chasing crooks for the agency; whether, once he had run out his string as an operative, he could have settled into a desk job bossing younger detectives. His Continental Op certainly speculates about the mental toll of such a life from time to time, still huffing after grifters though he is old enough to leave the field to the kids. The Op fears few things, but one of them is clearly his boss at the Continental’s San Francisco branch, known only as the Old Man, a pitiless, white-haired picture of what “fifty years of crook-hunting” can do to a human being. The Old Man is the Op’s cold-blooded future if he stays on, emptied of “everything except brains and a soft-spoken, gently smiling politeness” that is the same no matter how things turn out. Whatever the Op does in the service of his job, he must answer for in his reports to the Old Man, or skirt the truth and risk catching “merry hell.” Pontius Pilate, the ops call the Old Man privately, because he smiles sending them out on dicey missions to be “crucified.”

The Old Man first turned up in Hammett’s story “The Girl with the Silver Eyes” (1924), when the sleeping Op is summoned to the office on a Sunday morning by the “neat,” businesslike voice of his boss calling on the phone. Even in stories where he doesn’t speak, the Old Man’s detectives are often worrying aloud how to explain their code infractions to him. He makes a useful, grounding presence, the figure through which all trails of information converge in the office, and he gives direction to the men’s searches in the field: “If the Old Man said something was so, then it probably was, because he was one of these cautious babies who’ll look out the window at a cloudburst and say, ‘It seems to be raining,’ on the off-chance that somebody’s pouring water off the roof.” The Old Man bears a strong likeness to the best-known Pinkerton detective of all after the founder himself, James McParland,** longtime head of the agency’s Western Division, known to his admirers and enemies alike simply as the Great Detective. In 1911 the IWW leader Big Bill Haywood, who had survived a murder charge at the hands of McParland and Pinkerton’s, summed up the opinion of many in the labor movement:

When a detective dies, he goes so low that he has to climb a ladder to get into Hell—and he is not a welcome guest there. When his Satanic Majesty sees him coming, he says to his imps, “Go get a big bucket of pitch and a lot of sulphur, give them to that fellow and put him outside. Let him start a Hell of his own. We don’t want him in here, starting trouble.”1

In the latter years of his fame, with his white hair and grizzled mustache, his piercing, bespectacled gaze, and his thick, slouching body that had once been powerful, McParland looked very much as Hammett’s Op describes the Old Man:

A tall, plump man in his seventies, this boss of mine, with a white-mustached, baby-pink, grandfatherly face, mild blue eyes behind rimless spectacles, and no more warmth in him than a hangman’s rope.

During the decades that McParland ran Pinkerton’s Western Division, he made inspection tours of its satellite offices (Spokane, Seattle, Portland) every few months.2 As a Pinkerton, Hammett could not have overlapped with the Great Detective, as McParland died the same month Hammett was discharged from the army with TB, in May 1919. But the trail was hardly cold. Detectives would still be talking about McParland throughout the agency offices he’d supervised, two of which (Spokane and Seattle) employed Hammett. McParland’s reputation lingered long in San Francisco, too.

Dispatching a crooked superintendent in 1908, McParland sounds in his report every bit as hard as Hammett’s Old Man:

He said: “What! Am I discharged?” I replied: “Yes, what could you expect?” He said: “Won’t you allow me to resign?,” to which I replied: “No, I do not allow a man to resign who has admitted himself to be a thief and a forger and when conclusive evidence proves him to be a traitor … A man of your character should be killed and your carcass thrown to the dogs and if I killed you, Mr. Cary, in this room this minute I would not consider I would have to ask the forgiveness of God Almighty for doing so.” He immediately handed over the keys.3

Born in Armagh County, Ireland, in 1843, James McParland had joined the Agency in Chicago in 1871, after that city’s Great Fire claimed his liquor store. Two years later, he was working as a conductor on the rear platform of a Chicago streetcar one day, monitoring employee pilferage for the agency, when Allan Pinkerton spotted him while considering candidates for the assignment that would earn McParland his newspaper title, the Great Detective: infiltrating an Irish gang of Pennsylvania miners known secretively as the Sleepers, or Molly Maguires.

McParland met Pinkerton’s criteria for the dangerous posting: Irish-Catholic, unmarried, gregarious, “hardy, tough,” and conversant in the history of Northern Ireland’s secret organizations, a subject on which he wrote a seven-page treatise for his boss to secure the job. “If this man is mentally correct, and willing,” the founder thought, “he is just the instrument fitted for my mining operation.”4 Adopting an authentically shabby outfit and meticulous cover biography as James McKenna (whose backstory included a murder rap he was fleeing in Buffalo), McParland boarded a train and began wandering the Shenandoah Valley in search of any point of entry to the Mollies. A deadly outgrowth of the labor battles between the mining companies and a weakened union, the Molly Maguires committed acts of terror and murder against company executives as well as fellow miners who displeased them (especially Welshmen). In the late 1860s they killed at least a dozen men per year, a figure that had waned slightly by the time McParland arrived.

As James McKenna, McParland began a terrifying acting job of nearly three years undercover. His approach (later popularized in Allan Pinkerton’s The Mollie Maguires and The Detectives) has inspired every book or movie since in which a daring agent impersonates a thug to enter a criminal gang—swaggering into their pub headquarters to buy drinks all around, picking a fight with the largest man at hand, charming the gang’s leader with a political bar song, and bragging of his out-of-town scrapes with police to gain the thugs’ confidence.

The nervous weeks and months spent among his rough cast of new friends caused McParland to drop weight and lose his hair; he finally covered his head with a blond wig. Although he had become a Molly officer, he attempted to quit his Pinkerton’s assignment after information he had sent his contact was leaked and led to reprisal killings, including the shooting death of the wife of a Molly. But he was persuaded to stay on undercover, even though this event had cast suspicion among the miners that he was a detective. Eventually McParland had to make his nighttime escape by sleigh ahead of an armed and vengeful gang. Although it put his life further in jeopardy, in 1877 he testified in nine of twenty-three trials; nine Mollies were executed based directly on his testimony, twenty hanged overall.

After the gang had been decimated, McParland tracked down Western train robbers for Pinkerton’s before taking charge of the Agency’s Denver offices, which he ran almost to the end of his life (although, in 1903 he did write to New York for permission to finally take Sundays off). His fame crested with the 1907 murder case against leaders of the Western Federation of Miners, a conspiracy prosecution McParland seemed to model, rightly or wrongly, on his experience with the Mollies. A secretary at the Denver office later called him, without admiration, “the Dean of Black Sleuthdom.”

Hammett’s famous Op story “Flypaper” contains a conversation at the Continental office about other celebrated arsenic cases, and the Old Man knowledgeably references various techniques he has seen. In fact, McParland had once solved a nationally known Colorado case—the arsenic poisoning of Mrs. Josephine Barnaby, a widow visiting Denver from Rhode Island who died in April 1891 after drinking whiskey she had received as a gift in the mail. Unable to lay hands on the likely killer, Mrs. Barnaby’s physician and adviser, Thomas Thatcher Graves, who remained safely back east, McParland wrote the culprit a brilliantly fraudulent telegram inviting him to come west to testify and help put away someone else for his own crime. The killer packed at once and was indicted shortly after his arrival in Denver.5

Hammett was not the first to use McParland for fiction. The plot of Sir Arthur Conan Doyle’s final Sherlock Holmes novel, The Valley of Fear (1915), hinges on the career of a former operative named Douglas. It is a hybrid work: a typical Victorian murder mystery set on an English country estate with its own drawbridge gives way to a second tale after the discovery of an ugly American weapon, a sawed-off shotgun traced to Pennsylvania. At one point Holmes hands Douglas a cigar after the former op has given Dr. Watson a manuscript he has written about his undercover days in the Pennsylvania coalfields, a travail that has haunted the rest of his life. “I’ve heard of you, Mr. Holmes,” says ex-detective Douglas. “I never guessed that I should meet you. But before you are through with that [manuscript] you will say that I have brought you something fresh.” The honor is clearly a mutual one for the two sleuths, and the scene makes an odd acknowledgment of the “fresh” true story that Watson (Conan Doyle) borrowed to complete the book. (The latter part of the novel, Douglas’s savage tale of his undercover life among the American miners, contains neither Holmes nor Watson, who reappear only in the epilogue.)

The inspiration for the novel allegedly struck Conan Doyle when he met William Pinkerton on an Atlantic crossing, the real-life detective entertaining the English author by the fireside with the story of how his agency’s super-operative James McParland had brought down the Molly Maguires. Leaning heavily on the earlier account published by Pinkerton’s father, Allan, Conan Doyle produced The Valley of Fear, an act of appropriation for which William Pinkerton never forgave him. “The entire second part of that book of Doyle’s was taken from a book written by my father,” he told a reporter. “When I read it I dug up an old copy of my father’s book and sent it to Sir Arthur with my compliments. I never received a reply.”

If McParland inspired the characters of both Douglas and the Old Man, then he is the rare real person whose likeness appears in both Hammett and Conan Doyle, a human bridge of sleuthing worlds from the genteel to the hard-boiled.


* The title was spelled as The Big Knock-over in the original 1924 publication, but has been spelled throughout as it was in later reprints.

** He spelled it “McParlan,” like generations of his family in Ireland, until sometime in the 1880s, when, perhaps tiring of people hearing the d in his name anyway, he decided to legally add it, a small change compared to how so many other immigrants simplified their family names to “Americanize” their identities.

The agency was famously stingy with praise for its employees, and McParland’s later internal file (from 1880) does not reflect any increased value for his heroism: While his “General deportment and appearance” were considered those of a “genteel Irishman,” and he could “readily adapt” to all classes of people, he was rated “not good” as a shadow and his “knowledge of criminals” was considered poor.

Whenever William Pinkerton visited London, the tabloids hailed him as the American Sherlock Holmes; while Pinkerton knew the comparison was meant to be honorable, few things displeased him more. Good detecting, he repeated, was based on “common sense,” not brilliance.