Elizabeth Van Lew: “Crazy Bet” Brings Down Richmond

Statue of Elizabeth Van Lew looking towards a child while holding a history book
Kimberly J. Largent

During the Civil War, a handful of women dedicated their lives during those tumultuous years to spying. Whether their loyalties lay with the Union or the Confederacy, each was just as brave in their endeavors. These women often held little regard for their own personal well-being—they were daring, sometimes risking it all in order to hold true to their beliefs. One such woman was Elizabeth Van Lew, or “Crazy Bet” as Richmond citizens would come to call her during the war years. Elizabeth Van Lew, born October 12, 1818, was the oldest of three children born to John Van Lew, a successful Richmond hardware dealer, and Elizabeth “Eliza” Baker, daughter of Philadelphia mayor Hilary Baker. The Van Lews lived lavishly in an elegant three-and-one-half story mansion atop Church Hill outside of Richmond. They also owned a farm opposite City Point where crops were grown in fields worked by a dozen slaves owned by the Van Lews. That farm would later become an integral part of Elizabeth’s Richmond spy ring.

Elizabeth, considered the most stubborn of the Van Lew children, was well educated in both academia and social skills in Philadelphia. When back home in Richmond, it wasn’t unusual for her to be exposed to prominent visitors such as Edgar Allan Poe or Chief Justice John Marshall. All who met Elizabeth found her personality charming and her pale blue eyes and dark hair attractive. It was her father who had to contend with her stubbornness. The two never saw eye-to-eye on slavery and she often begged him to free the family slaves. He never acquiesced. Some considered her an abolitionist to which she wrote many years later years after the war: “I was never an abolitionist. Abolitionists are fanatics who will stop at nothing to achieve their goals. I have always spoke out against slavery, for which I paid dearly in the loss of many friends. But I was never a fanatic.” Elizabeth maintained a close relationship with her mother, and her closeness only intensified when her father died when she was in her twenties. Her first task after his death was to free the family slaves. Some stayed on with the Van Lews, others took advantage of their freedom and were never seen again. Regardless, during these years, Elizabeth didn’t hesitate to openly protest the beliefs of Richmond society—namely the issues of slavery and secession. She was so opposed to slavery, she spent her $10,000 inheritance on buying and freeing those slaves who were relatives of her freed slaves.

She openly stated: “ Slave power crushes freedom of speech and of opinion. Slave power degrades labor. Slave power is arrogant, is jealous and intrusive, is cruel, is despotic, not only over the slaves but over the community, the state.” Her views quickly brought her much criticism and many felt she was a Yankee sympathizer. She denied it saying she was only a “good Southerner who opposed slavery.” At the onset of the war, Elizabeth and her mother were asked to join the ladies of Richmond in making clothing for the Confederate soldiers. The two politely declined. When they found themselves recipients of criticism and threats, they reluctantly agreed to deliver religious books to the camps.

After the Battle of First Bull Run, Elizabeth began hearing horror stories of the conditions the Federal prisoners were forced to endure at Libby Prison. She quickly approached Libby Prison Commandant Lieutenant Todd (Mary Lincoln’s half brother) and requested a nursing position within the prison. She was denied. She continued up the chain of command, increasing her “charm” as need be, until her request was granted. From that point on, she visited the prison regularly and brought medicines, clothing, bedding and anything she could think of that would alleviate the prisoners’ suffering. Her frequent visits to the prison were not well-received by the citizens of Richmond. Elizabeth didn’t give a wit—and neither did Lt Todd who looked forward to her daily visits when she laded him with gingerbread and buttermilk. Within a short amount of time, Elizabeth held a commanding presence in the prison with both prisoners and guards. Each visit guaranteed her valuable information on Confederate strategy and strength. She began using her household staff, composed of freed slaves, to deliver messages to Union secret service agents. Messages would be carefully hidden in the hollowed-out sole of a shoe or in a basket of eggs that contained a “false” egg that had been emptied in order to hold the message. A Confederate officer finally forbid her to exchange any words with the prisoners during her visits.

Not one to be thwarted, Elizabeth began bringing books to the prisoners. With the books, she handed out a special cipher she’d created. The men would relay the tidbits of information they’d pick up from the guards by poking small holes under specific letters in the text of the books that when deciphered by her, would contain Confederate troop movements as well as strategies. As the war intensified, so did the animosity between Elizabeth and the citizens of Richmond and the Confederate officers at Libby. She decided to use the town’s assessment of her, calling her "Crazy Bet," to her benefit and began playing the role of a demented woman—taking every opportunity to mumble to herself as she walked the streets, allowing her appearance and attire to take on a disheveled look, and perfecting a confused expression. In reality, she was beginning to fear for the safety of her mother and herself.

Always the creative thinker, she decided the perfect solution to avoid Richmond retaliation was to open her home to the newly-arrived Libby Prison commandant who would be replacing Lt Todd. The new commandant accepted her gracious offer. Elizabeth soon enlisted the help of one of her freed slaves, Mary E Bowser, who Elizabeth had sent away to be schooled in Philadelphia years before. Mary was sharp and could read and write. It wasn’t long until the black woman found herself working as a servant in Jefferson Davis’ home. Mary wasted no time in rummaging through important papers on Davis’ desk and listening in on strategic conversations. Her razor-sharp memory allowed her to recall, verbatim, conversations she’d overhead and accurately reproduce maps she’d seen. With so much information getting through to the Union, Elizabeth became the object of suspicion, so much so her house was searched frequently.

However, nothing incriminating was ever found. Elizabeth took great care to keep her journal hidden—she buried it in the back yard. Once, according to one entry in her journal, she’d heard a band of Confederates were on their way to her home to confiscate her horse. She quickly brought the animal inside her home and led it up to the second floor where she hid him inside one of the secret rooms. The animal remained quiet during the search and was never found. In 1864, she began communicating directly with General Butler at Fortress Monroe. On February 28, 1864, she passed vital information on to Butler concerning a Confederate plan to move thousands of prisoners. Based on the information, the Union decided to try to capture the city. The plan failed and in the course of the fighting, 22-year-old Union Colonel Ulric Dahlgren, son of Rear Admiral Dahlgren, was killed. His dead body was further mutilated by the Rebels before being hastily buried in a shallow grave. Through her network, Elizabeth learned of the horrid deed and was able to locate the burial site. She had the body exhumed and placed in a coffin to be delivered to the Union troops.

Later, Jefferson Davis, not knowing the body had already been exhumed, compassionately ordered it be delivered to the Rear Admiral. Many Confederate soldiers were left scratching their heads when they found the grave empty. During the final year of the war, Confederate officials were still trying to obtain evidence against Elizabeth who by this time had added to her ring of many, a clerk in the Adjutant General’s Department at Richmond, an agent in the Confederate Engineering Department and a high-ranking official at Libby Prison. One evening, after preparing an important message on Richmond’s defenses, she headed for town with the balled up piece of paper. There, she walked the streets waiting for her scout to appear. He didn’t, but an unknown man walked abruptly by her and hoarsely whispered, “I’m going through tonight.” Elizabeth wondered if this man was a replacement, although her intuition led her to believe otherwise. She quickened her pace and walked by him only to hear the same phrase. Without stopping, she continued on her way without acknowledging him. The next day, she’d seen the same man on the street, this time he was marching with his Confederate regiment. They tried to catch her and they failed…again. It’s interesting to note that the high-ranking official at Libby Prison, known as “Ross,” was considered by many prisoners to be the most vicious of all the guards. He openly verbally abused the prisoners and without warning would launch a physical assault. He would then have the individual removed, most thought to be further tortured, if not killed. In actuality, he would get the prisoner alone, give him a Confederate uniform, escort him out of the prison and send him on his way to Elizabeth’s house where she would provide cover in secret rooms and passageways until it was safe to move the escapee to the next safe house. It was unfortunate that many Union prisoners didn’t know the real identity of the guard they came to loathe. But had they, he could have been exposed.

As General Grant moved his army nearer to Richmond, Elizabeth was able to communicate with him directly and on a daily basis. So perfected was her spy network, she was able to present him with a copy of the Richmond Daily Dispatch each day. General Sharpe, Grant’s Chief of Secret Service stated after the war that, “The greater portion of our intelligence in 1864-65 in its collection and in good measure in its transmission, we owed to the intelligence and devotion of Miss Elizabeth Van Lew.”

In April 1865, Confederate lines broke and Union troops entered Richmond. Elizabeth immediately raised an American flag above her home. A mob quickly gathered outside and threatened to burn her house down. Unlike the “Crazy Bet” they’d all come to know, she clearly and purposefully stepped forwarded and pointed a finger. “I know you and you…” she looked them in the eye. “General Grant will be here in town in an hour. You do one thing to my home and all of yours will be burned before noon!” The crowd slowly dissipated. Shortly thereafter, 2nd Lt David Parker arrived under General Grant’s directive to see if Miss Van Lew was in need of anything. She replied, “I want nothing now. I would scorn to have a guard now that my friends are here.” She then invited him to dinner. When General Grant arrived in Richmond, he had tea with Elizabeth.

After the war, President Grant rewarded her efforts by naming her Postmistress of Richmond, a post she held from 1869-1877, earning $1,200 a year. She then went on to Washington where she held a modest clerk position. She returned to Richmond years later and made reference in her journal, “No one will walk with us [referring to an invalid niece] on the street. No one will go with us anywhere; and it grows worse and worse as the years roll on.”

Elizabeth died at her home, surrounded by relatives, in 1900. She is buried in Richmond’s Shockoe-Hill Cemetery. The inscription on her headstone reads: “She risked everything that is dear to man—friends, fortune, comfort, health, life itself, all for the one absorbing desire of her heart—that slavery might be abolished and the Union preserved. The tombstone was a gift from Boston relatives of Colonel Paul Revere who was one of the many escaped prisoners she’d harbored in her home during the war. Source: Ryan, David, A Yankee Spy in Richmond: The Civil War Diary of “Crazy Bet” Van Lew, Stackpole Books 1996


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