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  • Gavin Whitehead

Anagramamaniacs - Lewis Carroll (S1E4)

Updated: Jan 31, 2023

Lewis Carroll was teaching math at Oxford when he befriended Alice Liddell, a colleague’s daughter. Even though their friendship ended in scandal, it led to one of the most beloved children’s books of all time, Alice’s Adventures in Wonderland. In 1996, psychotherapist Richard Wallace accused Carroll of committing the Whitechapel murders, claiming to have discovered compromising anagrams in Carroll’s writing. Show notes and full transcript below.

Above: Photograph of a twentieth-century American stage adaptation of Alice's Adventures in Wonderland. Taken from the Billy Rose Theater Collection at the New York Public Library.



An 1857 portrait of Lewis Carroll, first published by his nephew and early biographer Stuart Dodgson Collingwood in 1898.

Lewis Carroll photographed scores of children over the years, and some historians consider him one of the finest photographers of the nineteenth century. Titled The Dream and taken in 1863, this picture shows a little girl asleep on a chair. The ghostly images of a boy and a girl, created with the experimental technique of double exposure, can be seen to the right. Copyright held by the Victoria & Albert Museum, London. Accession No. RPS.2235-2017.

The original manuscript of Alice's Adventures in Wonderland, initially titled Alice's Adventures Under Ground. This document features Carroll's own handwriting and sketches. The author intended it as a Christmas present for Alice Liddell and included this inscription, dated November 26, 1864: ."A Christmas Gift to a Dear Child in Memory of a Summer's Day." Copyright held by The British Library Board, Catalogue No. Add. MS. 46700.

John Tenniel's illustration for "Jabberwocky," first published in Through the Looking-Glass, and What Alice Found There.

The infamous "Dear Boss" letter, written in red ink and received by the Central News Agency on September 27, 1888. The "trade name" of Jack the Ripper comes from this missive.

Taken from Carroll's 1889 book, The Nursery "Alice," this drawing shows three playing cards in the process of painting white roses red at the command of their queen. This illustration sets off alarm bells for Carroll's accuser, Richard Wallace, who sees it as a clue that the author has hidden an anagram in the corresponding text, featured below.



Passage from The Nursery “Alice"

“You see, there were five large white roses on the tree—such a job to get them all painted red! But they’ve got three and a half done, now, and if only they wouldn’t stop to talk—work away, little men, do work away! Or the Queen will be coming before it’s done! And if she finds nay white roses on the tree, do you know what will happen? It will be ‘Off with their heads!’ Oh, work away, my little men! Hurry, hurry!”

“Dodgson [i.e. Carroll] and Bayne seethe, tune, hone a weird way—any way—to laud my father’s holy work and let the hate vent. We plot how to kill dirty women, knife to throat. You see, to them it is such a large job to get five street whores all painted red. If I find one street whore, you know what will happen! ’Twill be ‘Off with her head!’ Work away! Hurry, hurry! Or the Queen’s little men will be coming before he’s done!”

Jack the Ripper Poem Included in Sir Melville Macnaghten's Memoir

“I’m not a butcher, / I’m not a Yid, / Nor yet a foreign skipper / But I’m your own light-hearted friend / Yours truly, Jack the Ripper.”

“But mother, I can! / O, I’m dainty! / Rip no gay peter foreskin. / I hated mother; fury built in don grew. / Jury, our tricks will trap ye!”

Montague Druitt's Suicide Note

“Since Friday, I felt I was going to be like mother, and the best thing for me was to die.”

“I fib, idiots. I – we – are fine faggot killers. C. Dodgson, T. Bayne threw me into the Thames.”



---Begg, Paul, Martin Fido, and Keith Skinner. The Jack the Ripper A-Z, Third Edition. London: Headline, 1996.

---Cohen, Morton N. “Dodgson, Charles Lutwidge [pseud. Lewis Carroll].” Oxford Dictionary of National Biography Online. Published Sep. 23, 2004, accessed Aug. 8, 2022.

---Cohen, Morton N. Lewis Carroll: A Biography. New York: A. Knopf: Distributed by Random House, 1995.

---Collingwood, Stuart Dodgson. The Life and Letters of Lewis Carrol (Rev. C.L. Dodgson). London: T.F. Unwin, 1898.

---Macnaghten, Melville. Days of My Years. New York: Longman’s, Green; London: Edward Arnold, 1914.

---Sugden, Philip. The Complete History of Jack the Ripper. New York: Carroll & Graf, 1994.

---Wallace, Richard. The Agony of Lewis Carroll. Melrose, M.A.: Gemini Press, 1990.

---Wallace, Richard. Jack the Ripper: “Light-Hearted Friend. Melrose, M.A.: Gemini Press, 1996.



Jack the Ripper wasn’t known for his poetry, but that doesn’t mean he never dabbled in verse. At the very least, somebody wanted police to think he had. In June 1889, Sir Melville Macnaaghten he had just started work as Assistant Chief Constable at the Criminal Investigation Department (the CID for short). The son of a high-ranking official in the East India Company, he had joined law enforcement some twelve months after returning to England from Bengal, where for sixteen years he’d managed his father’s estate. Ever the avid huntsman, Macnaghten funneled more time and energy into gunning down leopards, alligators, and what he refers to as “kangaroo hounds” than any other pursuit in East India. Much to his dismay, he arrived at Scotland Yard too late to take part in the hunt for the Ripper, which had more or less ended six months prior. That being said, curious artifacts of the killer’s reign of terror were still to be found lying around police headquarters. One day near the beginning of his tenure, Macnaghten was rummaging through a postbag bulging with letters related to the Whitechapel homicides when he happened upon four lines of janky verse. Their poor quality notwithstanding, they made such an impression that he put them in print almost twenty-five years later when preparing his memoirs. The poem reads. “I’m not a butcher, I’m not a Yid, / Nor yet a foreign skipper / But I’m your own light-hearted friend / Yours truly, Jack the Ripper.”

Already this season, commentators have cast the Whitechapel slasher as a master of disguise and a transformative actor. Now it’s time to meet Jack the Writer. In 1888 (and in some cases afterward), police received a gigantic body of letters signed Jack the Ripper. As will become evident, the killer’s enduring infamy depends in part on these diabolical documents.

If you ask psychotherapist Richard Wallace, the man responsible for the Whitechapel murders—along with a handful of Ripper letters—was a writer of truly exceptional talent, famed for his word games, anagrams included. Wallace’s suspect is none other than Lewis Carroll, “light-hearted friend” to children the world over and the whimsical architect of Wonderland. Today, we’ll hear about how Lewis met Alice, the real-life girl who to some degree inspired the fictional character, how their friendship ended in scandal, and how the author of Alice’s adventures wound up accused of serial murder roughly a century after his death.

As we go over the case against Carroll, we’ll hear about his alleged connection with—and betrayal of—Montague Druitt, one of the Metropolitan Police’s chief suspects around the time of the killing spree and indeed the favored candidate of Sir Melville Macnaghten. This is The Art of Crime, and I'm your host, Gavin Whitehead. Welcome to episode 4 of The Unusual Suspects . . .

Anagramamaniacs: Lewis Carroll


Charles Lutwidge Dodgson, better-known by his penname, Lewis Carroll, came into the world on January 27, 1832, the first son and third child of Charles Dodgson, a parish curate, and his wife, Frances Jane. According to Carroll’s nephew-biographer, Stuart Dodgson Collingwood, the family lived in “complete seclusion from the world,” on a farm in Daresbury, a hamlet of 143 residents separated from Liverpool by twenty-one miles. In 1843, Carroll’s father received a more lucrative job as rector in Croft-on-Tees, situated in North Yorkshire, prompting the family to relocate permanently.

To call Carroll precocious would hardly be an overstatement. Like his father before him, he had an inborn facility for the classics and math. In fact, Carroll was learning Greek and Latin by the age of five and would later listen, rapt, as the elder Charles held forth on the wonders of logarithms. When he wasn’t burying his nose in a book, Carroll roamed the gardens, fields, and barnyards of Daresbury, making pets of odd animals, according to Collingwood. On his many rambles, he may well have encountered the hedgehogs, dormice, rabbits, and caterpillars that would one day populate Wonderland. Speaking of Carroll’s creative streak, even as a boy, he’d evolved a sprightly imagination, writing verse and drawing pictures for his own amusement as well as that of his family.

At the age of fourteen, Carroll went away to a boarding school called Rugby, where he would pass four unhappy years. Pranking was rampant. Students lived in dens, and they might have walked in one afternoon to find their belongings—from furniture to picture frames—turned upside down. In certain respects, Carroll made for an easy target, supposedly more effeminate than other boys his age and far from athletic, and he certainly fell victim to bullying. On November 13, 1846, he had written his name, the date, and his Rugby house on one of his schoolbooks. Beside “Charles Dodgson,” a classmate had added “is a muff,” a jab at Carroll’s clumsiness on the sporting field. Worst of all was a practice referred to as “fagging.” This system of servitude required younger boys to fulfill their older classmates’ every whim, no matter how exacting or degrading. Chores included washing dishes in the scullery and running assorted errands. Moreover, the upperclassmen could slap their lackeys with what were known as “impositions,” arbitrary orders to write out hundreds of lines of Virgil or Homer within an allotted amount of time, often calculated to make the assignment hopelessly impossible. When the poor souls failed to satisfy their oppressors, they met with such punishments as public flogging.

Off to Oxford

Overcoming the daily indignities at Rugby, Carroll thrived as a student, winning several prizes. In 1851, he was off to Oxford. Despite being one of the most ancient and august universities in the world, Oxford admitted fewer undergraduates with intellectual aspiration than you might expect at this time. Much more common, Carroll’s biographer, Morton N. Cohen explains, were noblemen’s sons who were simply frittering away their time, not to mention their fathers’ money, as they waited to inherit family property. Also in high numbers were the offspring of country gentlemen, strapping outdoorsmen who had spent their teens astride of a horse and hunting game with the help of their dogs. Members of this group frequently brought animals and weapons to school, siccing their hounds on rats in their rooms and picking off pigeons outside with their rifles. Studying was an afterthought, if even that, and generally speaking, an air of frivolity pervaded campus.

While not unsociable, Carroll had always loved the companionship of books, and he took his studies much more seriously than many of his classmates. By way of example, late one night, Carroll was laboring over a paper on the life of Richard Hakluyt, a famous seventeenth-century geographer. Much to his surprise, he heard explosions at half past one. While he was toiling away by candlelight indoors, a gaggle of less scholastic young scholars had decided to set off fireworks outside in one of the quads. They were soon joined by several other troublemakers who threw bottles at windows before beating a retreat.

As he had at Rugby, Carroll filtered out the many distractions and earned the respect of his instructors as a result. In preparation for the “Greats,” the final exam for the Bachelor’s degree, he studied thirteen hours a day for three consecutive weeks, and his hard work paid off. Among other accomplishments, he took first-class honors in math, filling him with glee. In a letter to his sister, Mary, Carroll gushed, “[I]t will take me more than a day to believe it, I expect—I feel at present very like a child with a new toy, but I daresay I shall be tired of it soon, and wish to be Pope of Rome next.”

Sadly, a papacy wasn’t in the cards, but Carroll would stick to what he was good at for the rest of life, and life would seldom take him far from Oxford. In 1852, he received a studentship—a permanent fellowship—at his college, Christ Church, and in 1855 he began lecturing in mathematics there. Over the course of his academic career, he authored a number of mathematical treatises, many geared toward students instead of professors and some written with a certain amount of panache.

The Don, the Dean, and His Daughter

It was in his capacity as an Oxford don that Lewis Carroll befriended Alice Liddell. She was the second daughter of Henry George Liddell, an Oxford dean who had taken his position the same time Carroll had begun his studentship. As colleagues the two knew each other. On March 18, 1856, Carroll purchased a camera and lens, experimenting with—and excelling in—the relatively newfangled medium of photography, and Henry Liddell invited the math instructor to his home at the deanery to photograph his family. It was there, in the garden, that Carroll first glimpsed the three Liddell daughters, Lorina, Alice, and Edith. A brown-haired cherub with an angelic singing voice just shy of four when she met Carroll, Alice became his favorite of the trio. Over the course of the next seven years, a friendship blossomed as Carroll paid regular visits to the deanery, taking pictures of the girls, playing croquet in the garden, going for strolls, and making up stories off the top of his head. The Liddell daughters adored him with his marvelous camera and fantastical tales, and Carroll likewise treasured their friendship. Indeed, for the rest of his life, Carroll would have an affection for children, making friends with scores of them and even appearing to prefer their company to that of grownups.

Throughout the spring and summer of 1862, Carroll, the Liddell daughters, and various other adult companions undertook almost daily river expeditions, rowing to a nearby destination where they’d stop for a picnic. On July 4, they set out on one that would make literary history. That afternoon, they had boated to Godstow, upstream from Christ Church. Sometime after pulling ashore, the day-trippers sought shelter from the blazing sun, settling down in the shade of haycocks surrounded by a meadow. The girls begged Carroll to tell them a fairytale, and the consummate fabulist happily obliged. Spinning a yarn on the spot, Carroll sent Alice’s fictional counterpart tumbling down a rabbit hole without any foreknowledge as to where she would land. After returning his adventurer to the world above ground, Carroll would have assumed that this was the last that anybody would hear of her. He never put his impromptu tales down on paper—“[T]hey lived and died, like summer midges,” he recalled later, “each in its own golden afternoon.” But this time was different. One of Carroll’s “little maidens” petitioned him to write a copy for her. So he did.

Word Games in Wonderland

In 1865, three years after this river excursion, Carroll published Alice’s Adventures in Wonderland, an instantaneous critical and commercial success adorned with drawings by the masterly John Tenniel. Six years later, in 1871, he followed it up with Through the Looking-Glass and What Alice Found There, also illustrated by Tenniel.

These books have many charms, one of them being Carroll’s propensity for word games. On outings with the Liddell daughters, he amused and bemused them with riddles, puns, and anagrams, which all found their way into Alice’s adventures. Perhaps most impressively, he could also assemble sounds in strings of utter nonsense that almost sounded as if they made sense. The most famous example is in Through the Looking-Glass, when Alice hears tell of the dreadful Jabberwocky. The poem is so good and so short, it’s worth reading in full: “’Twas brillig, and the slithy toves / Did gyre and gimble in the wabe: / All mimsy were the borogoves, /And the mome raths outgrabe. / ‘Beware the Jabberwock, my son! / The jaws that bite, the claws that catch!/ Beware the Jubjub bird, and shun / The frumious Bandersnatch!’ / He took his vorpal sword in hand; / Long time the manxome foe he sought— / So rested he by the Tumtum tree / And stood awhile in thought. / And, as in uffish thought he stood, / The Jabberwock, with eyes of flame, / Came whiffling through the tulgey wood, And burbled as it came! / One, two! One, two! And through and through / The vorpal blade went snicker-snack! / He left it dead, and with its head / He went galumphing back. / ‘And hast thou slain the Jabberwock? / Come to my arms, my beamish boy! / O frabjous day! Callooh! Callay!’ / He chortled in his joy. ’Twas brillig, and the slithy toves / Did gyre and gimble in the wabe: All mimsy were the borogoves, / And the mome raths outgrabe.” Passages like this one make us think twice about the function of language in Carroll’s writing. According to Morton N. Cohen, his biographer, Carroll wants readers to ask, “[I]s the meaning of a word really the most important thing about it?” Words make sounds, after all, and “the sound of words, like music, makes us feel. Sound and feeling, in these books, are as important as, perhaps even more important than, sense and meaning.” What a wonderful way to make sense out of nonsense.

Exiled from Wonderland

For all the glory that Alice’s Adventures in Wonderland brought Carroll, the book was bound up with one of his darkest hours. His friendship with his muse fizzled out two years before the book published. Something happened in 1863, something to cause a rupture with her and her entire family. Overnight, the almost daily outings ground to a halt—gone were the strolls, the river expeditions, and the games of croquet. Carroll reestablished ties about six months later, to be sure, but they remained loose. More likely than not, we will never know what opened this rift because of a yawning gap in the record. Carroll’s diary contains no entries for June 27, 28, or 29, 1863, and it’s not simply because he skipped those days. He appears to have recorded the events of those dates on a single page, and that page has gone missing, removed years later by another’s hand. By her own admission, Carroll’s niece, Menella Dodgson, cut several leaves from her uncle’s diary because they had offended her sensibilities, including the absent page in question. Whatever she read there so perturbed her, she had taken a razor to it, ensuring that posterity would never see its contents.

In trying to piece together what occurred, we have little more to go on than Oxford tattle. At the time, the word around town was that Carroll had “proposed marriage” to Alice. According to Cohen, it’s not so easy to dismiss this rumor as baseless hearsay. It stuck around for years and even the skeptical-minded appear to have credited it. In 1878, almost two decades after the falling-out, Prime Minister Lord Salisbury wrote in a letter, “They say that Dodgson [i.e. Carroll] has half gone out of his mind in consequence of being refused by the real Alice. It looks like it.” Cohen describes Salisbury as “an archenemy of gossip and speculations about people’s private lives,” so coming from him, this remark lends some credibility to the reported marriage proposal.

In 1863, Carroll was thirty-one, and Alice eleven. This alone is disturbing, but so were the laws on legal capacity to marry. At the time, girls could wed at the age of twelve, so in the eyes of the law, Alice could have walked down the aisle with Carroll as soon as she’d celebrated her very next birthday. For his part, Cohen doubts whether Carroll got down on one knee and proposed outright—even under normal circumstances, such effrontery wasn’t encouraged by the customs guiding Victorian courtship. Among other possibilities, he speculates that Carroll might have suggested a future alliance once Alice was older. Whatever happened, it clearly appalled her mother and father and kept neighbors talking for years to come.

Based only in part on his feeling for Alice, many have concluded that Carroll was likely a pedophile. That being said, scholars are divided on whether he desired prepubescent girls, and if so, to what extent he may have acted on his attractions. Even light googling will reveal that much could be said about this complex topic, and I’ll leave that to you if you’d like to learn more.

Those who do believe Carroll to have been a pedophile suspect that his longings may contributed to his tormented inner life. For all his levity as a children’s author, he carried around feelings of smoldering self-hatred and spiritual despair. His diary offers a window onto his inward anguish. As Morton N. Cohen points out, a number of particularly vicious outpourings of self-recrimination cluster around the early-to-mid 1860s, the years before and after the schism between Carroll and the Liddell clan, suggesting perhaps that his attachment to Alice as well as its sundering may have added fuel to the fire raging within him. On December 28, 1863, six months after his unknowable offense, Carroll writes, “God grant that with this dying year may die in me all the old and evil life, and that a new life may begin.” On the final day of 1864, he’s back to self-flagellating: “I desire to record my intense gratitude to God, for his abundant mercy, in having spared me suffering and sorrow, and given me many and great pleasures—and my shame and sorrow for the sin, the coldness and hardness of heart by which I have provided Him—and a prayer, from my heart, that He will grant me grace to put away the old sins of the dead year, and with this coming year to begin a holier and better life.” This inner turmoil figures prominently in the case for Carroll as Jack the Ripper.

Letters from Hell

But before we get to that, let’s have a look at the Ripper’s supposed output as a writer. If all the letters bearing his name are to be believed (most of them aren’t), then in the autumn of 1888, the killer had filled more pages than Charles Dickens could have in an entire year, and Dickens could churn out a doorstop-novel like nobody’s business.

Why not start at the beginning? On September 27, the Central News Agency—the CNA—received a letter, the address scribed in blood-red ink on the envelope. The missive inside consisted of two pages, written with a confident, educated hand and likewise penned with scarlet lettering. It makes reference to the Leather Apron debacle as well as the theory that a doctor may have carried out the murders, both of which we covered in the previous episode. Usually called the “Dear Boss” letter and pictured on the Art of Crime website, it reads as follows: “Dear Boss, I keep on hearing the police have caught me but they wont fix me just yet. I have laughed when they look so clever and talk about being on the right track. That joke about Leather Apron gave me real fits. I am down on whores and I shant quit ripping them till I do get buckled. Grand work the last job was. I gave the lady no time to squeal. How can they catch me now. I love my work and want to start again. You will soon hear of me with my funny little games. I saved some of the proper red stuff in a ginger beer bottle over the last job to write with but it went thick like glue and I cant use it. Red ink is fit enough I hope ha. ha. The next job I do I shall clip the ladys ears off and send to the police officers just for jolly wouldn't you. Keep this letter back till I do a bit more work, then give it out straight. My knife's so nice and sharp I want to get to work right away if I get a chance. Good Luck. Yours truly Jack the Ripper.” Two postscripts follow, the first of which reads, “Dont mind me giving the trade name.” Written at a right angle to the rest of the text, the second states, “wasn’t good enough to post this before I got all the red ink off my hands curse it. No luck yet. They say I'm a doctor now. Ha ha.”

On September 29, the CNA forwarded this letter to Scotland Yard. At first, the police appear not to have considered it worth following up on, writing it off as a morbid hoax. They would be forced to reconsider in less than twenty-four hours.

On the morning of Sunday, September 30, the Ripper claimed the lives of Elisabeth Stride and Catherine Eddowes. The following day, the CNA received yet another communication signed Jack the Ripper, this time a postcard. Shorter than the first and stained with what appears to be blood, it reads: “I was not codding dear old Boss when I gave you the tip, youll hear about saucy Jacky’s work tomorrow double event this time number one squealed a bit couldnt finish straight off. had not time to get ears for police thanks for keeping last letter back till I got to work again. Jack the Ripper.” Evidently taking this seriously as a lead, the Metropolitan Police had facsimiles of both “Dear Boss” and what is known as the “Saucy Jacky” postcard published in newspapers, hoping that someone would recognize the handwriting and identity the author.

Could these epistles have come from the murderer? After all, in the “Dear Boss” letter, the Ripper had hinted that he would soon resume his “funny little games.” Three days after the author mailed the missive, the slayer struck twice in a single night. More curious still, in “Dear Boss,” the sender had promised to clip off his next victim’s ears and post them to the police. No such delivery had arrived at the Yard, but this detail stuck out because of what the Ripper had done to Eddowes. While mutilating her face, he’d cut off part of her right ear, leaving it behind at the scene of the crime. Whoever authored the “Dear Boss” letter certainly appared to have written the “Saucy Jacky” postcard. The former’s handwriting resembles that of the latter. In the postcard, moreover, the author harkens back to the promise he made in “Dear Boss” to lop off ears and mail them. Appearing to explain why the gruesome parcel never materialized, he claims that he “had not time” to remove the body parts. Seemingly adding to the postcard’s authenticity, the letter writer knew about the homicides before most of the public. The murders had taken place early Sunday morning, and the sender was supposed to have written the postcard that same day. Most newsrooms were empty on Sundays, creating a lag in the news cycle, and for this reason the double event—a term introduced in the “Saucy Jacky” postcard—would not reach much of the public’s attention until Monday, when the presses were churning out papers again.

Nevertheless, observers disputed these letters’ authenticity almost as soon as they arrived at the Yard. While many accepted them as genuine at the time, others rolled their eyes, dismissing them as pranks. One theory held that profit-hungry newspapermen had fabricated the messages for a very simple reason: much like sex, murder sells. Along with several other policemen, Sir Melville Macnaughten took this view, recalling in his memoirs: “In this ghastly production I have always thought that I could discern the stained forefinger of the journalist—indeed, a year later, I had shrewd suspicions as to the actual author!” According to the authors of The Jack the Ripper A-Z, today, “most researchers” conclude that a journalist was pulling one over on the public.

They’re even less convinced by the rest of the Ripper correspondence. After “Dear Boss” and “Saucy Jacky” were published, hundreds—some have claimed thousands—of imitations deluged Scotland Yard, many of them purporting to have streamed from Jack the Ripper’s pen. They flew in from all across Britain and even the United States. Either the Ripper was quite the globetrotter and never left home without his inkwell or we’re dealing with a bunch of Victorian trolls, hoaxers who wrote in for no reason other than to belittle the police. Needless to say, most researchers lean toward the latter.

Authentic or not, the Ripper correspondence, particularly “Dear Boss” and “Saucy Jacky,” have shaped the way we think about the murderer in at least two ways.

First and foremost, they gave him a name. That’s right, the “trade name” of Jack the Ripper appears for the first time in the “Dear Boss” letter. Thanks to the publicity, it soon caught on as the favored nickname. Researchers have pondered why the letter writer went with “Jack the Ripper.” The “Ripper” bit is obvious. It refers to the murderer’s trademark mutilations. But why Jack? Most straightforwardly, the sender may have chosen it as a generic male name, as if to imply that any man in London could have committed the murders. By this logic, the suspect pool grows to encompass roughly half the adult population, so in this sense the nom de plume plays up the mystery of the killer’s identity. Other commentators perceive a resonance with the name of another notorious English delinquent, Jack Sheppard, a carpenter-turned-thief who shoplifted and burgled in the early eighteenth century, a time when criminals convicted of those offenses went to the gallows. Sheppard was arrested and escaped from prison no fewer than four times, winning notoriety. He was hanged in the end, but more than 150 years later, Sheppard still loomed large in popular culture, and most Victorians would have known—and in some cases admired—him. Still other researchers have linked the sobriquet of Jack the Ripper with a monster from nineteenth-century folklore: Spring-heeled Jack. First sighted in London in 1837 and supposedly spotted many times after, this demon was possessed of dagger-like claws and fiery eyes, as well as the ability to spit blue flame. Appearing as if from nowhere, he rushed at his victims, usually young women, and ripped their clothing with his fingertips. They called the devil “Spring-heeled Jack” because he could leap with superhuman agility, whether in and out of the path of oncoming traffic or up and over walls that were nine feet tall, shrieking with laughter as he vanished from view.

In addition to a name, “Dear Boss” and “Saucy Jacky” gave the killer a personality, or at least one observers have liked to project onto him. This guy revels in malevolence. True, he thinks of murder and mutilation as labor, calling his horrific crimes his “work,” but work and play are one and the same to him. After all, he’s raring to resume his “funny little games.” Cocksure in the extreme, he fancies himself expert at what he’s playing. “How can they catch me now[?]” he gloats. If homicide is his idea of entertainment, so is taunting law enforcement, and he wants to get a rise out of the head honcho—the “Boss” of “Dear Boss” appears to refer to Sir Charles Warren, chief commissioner of the Metropolitan Police. “Ha ha” echoes throughout the first missive. The killer’s howling till his sides hurt over the coppers’ blunders and dunderheaded theories, their Leather Aprons and homicidal medicos, red herrings all of them and wastes of time. He wants his insults to sicken as much as they sting, so he’s filled up ginger beer bottles with blood to use for ink. Even if the actual murderer didn’t author these letters, the exultant villainy leaping off the pages has captivated readers past and present.

Along with “Dear Boss” and “Saucy Jacky,” one further piece of Ripper correspondence has received considerable attention from researchers, even though the sender doesn’t sign off as “Jack the Ripper.” Many have questioned its genuineness. At the same time, I’ve come across more than one writer who has rejected “Dear Boss” and “Saucy Jacky” as pranks while also concluding that this dispatch may have been legitimate. The letter in question arrived in a package, but what has given Ripperdom reason to suspect its authenticity has less to do with the missive itself and more to do with the enclosure that came with it.

The parcel was mailed to the home of George Lusk, a Whitechapel carpenter who specialized in refurbishing music halls. Lusk served as chairman of the Whitechapel Vigilance Committee, which had convened for the first time on September 10, two days after Annie Chapman’s murder. Frustrated by law enforcement’s failure to apprehend the killer, sixteen local tradesmen formed the organization with the aim of upping security on the streets. To that end, they recruited unemployed East Enders to patrol the Ripper’s hunting ground every night between 12 a.m. and 4 or 5 in the morning. Each of these sentinels pulled on a pair of rubber-soled galoshes before starting his shift, allowing for stealth as he walked the district. He also carried a police whistle as well as a cudgel. For their services, these watchmen took home a modest though much-appreciated wage. As chairman, Lusk was the face of the Whitechapel Vigilance Committee. Along with his treasurer, Joseph Aarons, Lusk garnered publicity by writing letters to the Daily Telegraph, beseeching Home Secretary Henry Matthews to offer a reward for tips that might lead to the murderer’s capture. Through his work for the Vigilance Committee, Lusk had emerged as a bulwark of justice in the community. He had also put a target on his back.

The date was October 16, about two-and-a-half weeks after the double event. Lusk was holding a three-inch cardboard box in his hands. Inside, he found a chunk of raw meat, clearly severed from a larger piece. The carpenter must have wondered what was afoot until turning his attention to the enclosed. Evidently Lucifer himself had mailed the package, based on two words scrawled in curly cursive in the upper right-hand corner: “From Hell.” As his eyes ran over the rest of the text, Lusk would have recalled with a shudder that the Whitechapel murderer had removed internal organs from Eddowes. If this letter was telling the truth, he was looking at one of them—part of one, at least—and the killer had added cannibalism to his list of barbarities: “Mr Lusk, Sor I send you half the Kidne I took from one women prasarved it for you tother piece I fried and ate it was very nise. I may send you the bloody knif that took it out if you only wate a whil longer signed Catch me when you can Mishter Lusk.”

In Lusk’s estimation, the letter from hell was not to be credited. Some twisted hoaxer had probably gotten his hands on a dog’s kidney and put it in the mail, hoping to scare him. His friends were less certain and prevailed on him to have it examined by a medical professional. Curator of the Pathology Museum at London Hospital Dr. Thomas Openshaw performed an analysis, and going on the press reports, it looked like the organ could have come from Eddowes’ body. Openshaw had referred to the kidney as “ginny” (i.e. gin-soaked), determining it to have belonged to a woman of forty-five who was afflicted with Bright’s disease. It had been removed in the past three weeks. The following day, however, Openshaw came forward with a series of corrections that must have disappointed sensationalists. Reporters had printed not what he told them but what would sell papers. He had merely identified the organ as human and concluded that it had been preserved in spirits of wine. This clarification plus other medical opinions, seemed to have resolved the matter, yet a series of twentieth-century revelations, including the unearthing of meticulously detailed contemporary medical reports, have led some to believe that indeed the murderer had mailed the package.


According to child psychiatrist Richard Wallace, several pieces of Ripper correspondence came from the pen of Lewis Carroll. In 1996, Wallace published his book, Jack the Ripper, Light-Hearted Friend, implicating the children’s author in the Whitechapel nightmare.

Wallace bases many of his arguments on anagrams he believes Carroll to have hidden in his writing. He even unscrambles the alphabet soup of “the Jabberwocky” to reveal a hidden message. Wallace never says why he’s opted for this methodology. He does point out that Carroll entertained friends both young and old with anagrams, gaining recognition as “an undisputed master” of this form of wordplay.

Carroll had mastered the subtle art of anagramming. Take, for example, the trick he played with the name of Prime Minister “William Ewart Gladstone,” one of nineteenth century Britain’s most eminent liberal politicians. More conservative in his own political views, Carroll poked fun at Gladstone’s radicalism, shaking up the letters in his name to spell, “Wild agitator! Means well.” In another, Carroll rejigs the name of Florence Nightingale, the groundbreaking nurse who had lent her profession new respectability through her endeavors in the Crimean War, which lasted from 1853-56. Even better than the other, this one goes, “Flit on, cheering angel!” Much like nightingales, angels take flight, so the command to “flit on” dovetails splendidly with both the nurse’s surname and the heavenly being. Give him a name, and “presto chango!” Carroll could take it apart and put it back together to form a completely different, complex sentence, sometimes possessed of poetic merit.

Profiling Carroll, Wallace calls him “a boy who was destroyed in childhood.” It started at home, Wallace insists, with overbearing parents who molded him into their idea of the perfect son, demanding that he grow up more quickly than he ought to have. If Carroll’s mother and father had done grievous harm, his utter annihilation awaited at Rugby, his boarding school. Without hard evidence, Wallace argues that Carroll suffered sexual violence at the hands of older boys as part of the so-called “fagging” system. This traumatic episode triggered what Wallace calls “a psychotic break from which he never recovered.” For the rest of his life, Carroll harbored psychopathic rage. Adding to his fury was the unresolved issue of his sexuality. Wallace does not view Carroll as a probable pedophile, considering it more likely that he was gay instead. Angry at the world, Carroll resented his mother most of all. As much as he abhorred her for doing her part to deny him a childhood, Wallace suggests, he also felt betrayed and abandoned by her. In his first year at Oxford, after all, she had died suddenly, devastating him. Taking revenge on the wrongs he felt his mother had done him became an obsession. To that end, Carroll engaged in secretive antisocial behavior that came to a terrible climax with the Whitechapel murders in 1888. The women he murdered stood in for his mother, little more than objects he could toy with to purge his rage. For reasons Wallace never fully explains, he also suspects that Thomas Veare Bayne, a fellow Oxford don, acted as an accomplice in the Whitechapel atrocities. Before moving on, I should point out that Wallace calls Carroll by his given name, Charles Lutwidge Dogdson.

According to Wallace, Carroll couldn’t help disclosing his crime. More than that, he’s hidden his confessions in plain sight.

Let’s start with The Nursery “Alice,” which Carroll began in 1888 and published early the following year. As Carroll states in the preface, he intended this simplified version of his story to be read by children five and younger—and if not read, since not everyone can read before five, then at least lovingly thumbed, cooed over, and dog-eared. In one passage, Alice crosses paths with a couple of playing cards employed as gardeners by the Queen of Hearts. They’re standing in front of a tree with white roses in its branches, and their sovereign has ordered them to paint the flowers red. One paragraph sets off alarm bells for Wallace. Carroll has written this passage for The Nursery “Alice”—it appears nowhere in Alice’s Adventures in Wonderland. Here’s what it says: “You see, there were five large white roses on the tree—such a job to get them all painted red! But they’ve got three and a half done, now, and if only they wouldn’t stop to talk—work away, little men, do work away! Or the Queen will be coming before it’s done! And if she finds nay white roses on the tree, do you know what will happen? It will be ‘Off with their heads!’ Oh, work away, my little men! Hurry, hurry!” Wallace finds the passage so fishy because of a discrepancy between image and text. While the playing card stresses that five white roses need to be painted, six flowers are shown in an accompanying illustration. Far from an oversight, this is a clue that the passage is an anagram. Rearranging the letters, Wallace unveils a murder confession, sitting right there for any five-year-old to find it—you know, provided she could read and also understood the concept of an anagram. Unlike Carroll’s lucid and clever rearrangements of names, Wallace’s decrypting of this passage makes hardly any sense at all, and it might sound confusing when I read it out loud. If you want to have a look at it for yourself, check out the Art of Crime website where I’ve posted it, along with the original, unscrambled text. The shaken-up paragraph reads as follows: “Dodgson [i.e. Carroll] and Bayne seethe, tune, hone a weird way—any way—to laud my father’s holy work and let the hate vent. We plot how to kill dirty women, knife to throat. You see, to them it is such a large job to get five street whores all painted red. If I find one street whore, you know what will happen! ’Twill be ‘Off with her head!’ Work away! Hurry, hurry! Or the Queen’s little men will be coming before he’s done!” A lifetime of hatred—especially toward women—comes through, according to Wallace. Much like the author of the “Dear Boss” letter, moreover, Carroll even mocks the authorities, demeaning them as “the Queen’s little men.”

Wallace also scours the Ripper correspondence on the lookout for anagrams. Of paramount importance is the poem I read at the beginning of this episode and from which he’s taken the title of his book. Here it is again to refresh your memory: ““I’m not a butcher, / I’m not a Yid, / Nor yet a foreign skipper / But I’m your own light-hearted friend / Yours truly, Jack the Ripper.” Wallace dismantles and reconstructs it, line by line, and again I’ve posted his solution on the website if you want to have a gander at it. This one highlights Carroll’s resentment of his mother, his well-known effeminacy, and as well as his supposed homosexuality. It reads: “But mother, I can! / O, I’m dainty! / Rip no gay peter foreskin. / I hated mother; fury built in don grew. / Jury, our tricks will trap ye!” … I’m going to go ahead and leave that one alone.

Jack is Dead and Never Coming Back

Wallace has even more of a tale to tell, and he won’t stop at pinning these murders on Lewis Carroll, beloved children’s author and the man you’d least suspect. He claims to have discovered a possible connection between Carroll and another Ripper candidate who’s gotten a lot of attention over the years.

This story starts with a recently retired Melville Macnaghten. In his 1914 memoir, Days of My Years, Macnaghten made clear that he was sitting on a secret. He asserts with cool authority that Jack was dead and never coming back. After the murder of Mary Jane Kelly on November 9, 1888, what he calls that “awful glut” at Miller’s Court, the Whitechapel menace had descended into madness before diving into the Thames, drowning himself. Partly out of respect for surviving relatives, the retiree kept the suspect’s name to himself. If Melville Macnaghten were to be believed, then, he knew who’d perpetrated criminal history’s most notorious murders. He just wasn’t going to tell.

For the next forty-five years, that was it. The general public had no idea who Macnaghten was talking about until 1959, when broadcast journalist Daniel Farson tore back the veil concealing the suspect. While preparing a special program on the Ripper, he happened to meet Lady Christabel Aberconway, one of Sir Melville Macnaghten’s daughters. She had copied out her father’s notes by hand shortly after his passing in 1921 and offered to share them with the broadcaster. When Farson took her up on it, he had no inkling of what he would uncover. These papers included a copy of a draft of a private memorandum Macnaghten had made on February 23, 1894. This memo named three police suspects in the Ripper investigation, including the man to whom Macnaughten had alluded in Days of My Years. In one of several versions of the document, the suspect lineup includes a Polish Jew, later identified as Aaron Kosminski, and a “mad Russian doctor” called Michael Ostrog. Neither looked good as a suspect to Macnaghten. His top candidate was “a doctor of 41 years of age” who answered to the name of Montague Druitt.

The Tragic Death of Montague Druitt

In truth, Montague Druitt was neither forty-one at the time of the murders, nor was he a doctor. That being said, his life had come to a tragic conclusion shortly after that awful glut at Miller’s Court.

The son of a surgeon, Druitt was born on August 15, 1857, graduating from New College, Oxford with third-class honors in classics in 1880. That same year, he secured a teaching position at a boys’ school in Blackheath, South East London. In 1881, he set out to become not a doctor but a lawyer, staying on as a schoolmaster to pay for his training. He was called to the bar in 1885.

The remainder of his life saw a succession of tragedies. His father died of a heart attack in September 1885, and Montague’s mother slowly slipped into mental illness afterward. By July 1888, her condition had grown so dire that she was admitted to an asylum. Druitt continued teaching at Blackheath until November 30, at which point he was fired without explanation. Whatever caused his dismissal, on December 11, Montague’s brother, a solicitor named William, received unsettling news. Nobody had seen Montague for more than a week.

All signs pointed to suicide. On December 31, 1888, a waterman discovered Druitt’s body floating in the Thames, alerting a policeman without delay. Fully dressed but for his hat and collar, he had placed four stones in each of his upper-coat pockets and thrown himself in. Based on the state of decomposition, an examiner judged him to have been underwater for the better part of a month. Working with this estimate, Druitt’s death had likely occurred a few days after his sacking, which may or may not have motivated his suicide. Montague himself had given another reason. At his inquest, William Druitt presented a note he had recovered from his brother’s chambers. It said simply, “Since Friday, I felt I was going to be like mother, and the best thing for me was to die.” Based on the note, Montague had killed himself because he feared that his mind was fracturing, like his mother’s had.

The Ripperverse went wild over this revelation, and Druitt struck many as the most likely suspect throughout the 1960s, the decade after his name came to light. A senior police official with access to confidential records had pointed the finger at him. Furthermore, his death in December 1888 answered one of the most vexing questions in all Ripperdom—why had the killer stopped killing when he did? Druitt may have grown violent due to mental illness, researchers assumed, and it was thought that he might have absorbed the requisite medical knowledge from his father, a surgeon.

Then and since, however, skeptics have rejected Druitt as the culprit. There’s nothing to connect him with the crimes, they point out, and so what if he committed suicide shortly after the killing spree end. It could have been a coincidence.

Richard Wallace has other ideas.

Carroll taught math at Oxford University, where Druitt had studied as an undergraduate. On December 12, 1878, Carroll noted in his diary that he had given a bed to a fellow named “Drewitt.” Weakening the link, Wallace concedes, Carroll spells the surname “D-R-E-W-I-T-T” whereas Montague Druitt spelled his with a “U,” as in “D-R-U-I-T-T.” Adding another layer of ambiguity, Carroll seems to have scribbled “Moutnay” as the first name—not the same as “Montague,” to be sure, but not so different either.

Based in part on this tenuous thread, Wallace asks whether Druitt may have taken part in the Whitechapel atrocities. Not only that—Druitt is supposed to have been just as much an anagramamaniac as Lewis Carroll. Near the end of Light-Hearted Friend, in what Wallace prefaces as “the most startling and unexpected finding in all this research,” he rearranges the letters in Druitt’s suicide note to reveal a covert communication. Just so you know, it contains what today has become a homophobic slur—the worst of its kind, in fact. After unveiling this anagram, Wallace hastens to add that this epithet was a derogatory term not for gay men but rather for women in the Victorian period. So, bearing that in mind, let’s hear Druitt’s revelation: “I fib, idiots. I – we – are fine faggot killers. C. Dodgson, T. Bayne threw me into the Thames.” Wallace’s thinking is hard to follow here, but he would seem to have us believe that Druitt himself wrote this message—Dodgson and Bayne “threw me into the Thames,” the author declares. If so, we’re to understand that Druitt participated in the Whitechapel homicides and then somehow divined that Carroll and Bayne were going to kill and frame him for the murders, allowing police to believe they’d fished the sole culprit out of the Thames. In a sudden flash of inspiration, Druitt authored what only appeared to be a suicide note. In truth, it was an anagram, exposing Carroll and Bayne as accomplices. At this point in Light-Hearted Friend, the implications of Wallace’s argument become so convoluted even he cannot make sense of them. As if throwing his hands in the air, he admits that future researchers will have to dig deeper before we can get to the bottom of this Druitt business.


As far as I can gather, nobody has. Which might have to do with Light-Hearted Friend’s brutal reception.

Among other flaws, critics have faulted the notion that Wallace’s anagrams prove his case. They tell you less about Carroll than they do about what Wallace wanted to find in Carroll. If a passage gives you enough letters to mess with, you can rearrange them to say pretty much whatever you want—that’s how language works. For whatever reason, Wallace had a mind to demonstrate that Carroll had committed the Ripper killings and went looking for evidence to support that theory. Lo and behold, he found what he was after—not because he’d uncovered the unspeakable truth but rather because he’d been manipulating language the way anybody could. Someone else could have consulted the exact same passages in The Nursery “Alice” or and the Ripper correspondence and come up with anagrams pinning the assassination of Abraham Lincoln on Carroll if they wanted to.

Guy Jacboson and Francis Heamey make precisely this point, though not by having their way with Carroll’s writing. In November 1996, Harper’s magazine excerpted a passage from Light-Hearted Friend. Part of it reads: “This is my story of Jack the Ripper, the man behind Britain's worst unsolved murders. It is a story that points to the unlikeliest of suspects: a man who wrote children's stories. That man is Charles Dodgson, better known as Lewis Carroll, author of such beloved books as Alice in Wonderland.” Jacobson and Heamey reordered the letters in these three sentences to implicate Wallace in the most sensational murder of the ’90s. Their response ran in the letters column of Harper’s February 1997 issue: “The truth is this: I, Richard Wallace, stabbed and killed a muted Nicole Brown in cold blood, severing her throat with my trusty shiv's strokes. I set up Orenthal James [i.e. O.J.] Simpson, who is utterly innocent of this murder. P.S. I also wrote Shakespeare's sonnets, and a lot of Francis Bacon's works too.”

In Wallace’s own words, his “story” points an accusatory finger at “the unlikeliest suspect.” Carroll is an unusual suspect, but as we’ll see, he’s in good company. Over the next three episodes, we’ll look at a series of increasingly ornate theories, each of which builds on the one that came before. It all kicks off with the tale of a poet who tutored a prince.


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