As much as Elizabeth was able to help the prisoners of Libby Prison, they were still subject to much neglect and abuse. A guard named Ross held the distinction of being one of the most vicious, both verbally and physically. It was well known that Ross would choose a single prisoner to receive the brunt of his violence. At first this took place around all of the other prisoners, but eventually Ross would drag the man off for a private interrogation. No man ever returned from these meetings, which fueled the terror of Ross’s reputation. Little did the prisoners know, or anyone else in the prison for that matter, that Ross was actually working for Elizabeth Van Lew. Instead of torturing the prisoners he drug off, he would outfit them with a Confederate uniform, escort them outside, and direct them to the mansion on Church Hill - their first stop on the Underground Railroad.
Amazingly enough, Ross was not Elizabeth’s best-placed spy. That distinction belongs to Mary Elizabeth Bowser. Mary was freed from slavery as a child by the Van Lew’s. Recognizing that Mary was not just intelligent, but gifted, Elizabeth sent her north to be educated. After the outbreak of the Civil War, Mary returned to Richmond and at the request of Elizabeth became a spy. Working through a friend, Elizabeth got Mary placed as a maid in the White House of the Confederacy. Since Mary was black, and at that time it was illegal to teach slaves to read and write, everyone assumed that she was illiterate. Since she was black and a woman, they assumed she was dumb as well. Mary let them believe this, and fell into the role of the perfect southern servant – servile and industrious.
Mary was so industrious, she made sure that everything in President Davis’s office was dust free and polished at all times. If that meant she had to linger while a meeting was going on, or rifle through maps and correspondence to get to the surface of a desk or table, then she did what had to be done, and the powerful men all around her were blinded by their prejudice. She read and overheard all that she could, and using her photographic memory, copied it out later to pass on.
It quickly became obvious that there was a leak in the White House. However, the investigation into that leak focused on the most likely suspects, white men. This provided Mary months to continue collecting data. When the investigation finally turned its focus to the servants, Mary was forced to flee, but she took the time to set fire to the White House before she fled. This provided her with time to escape, but was put out before any real damage could be done. Because Mary’s actions and escape were so high-profile, she was moved out of the south via the Underground Railroad.
As more and more information leaked out of Richmond, Elizabeth found herself under ever-increasing scrutiny. Her house was regularly searched – they never found the documents which she kept buried in the backyard or her secret room upstairs – and the Confederates laid several traps for her. They tried to catch her accepting information, they tried to catch her passing information, they even sent one their agents, dressed as a Union soldier, to her back door in the middle of the night seeking refuge. None of their traps worked.
In an attempt to quiet her harshest critics, Elizabeth offered to provide room and board for the new Commandant when he was installed at Libby Prison. After all, how could she possibly run a spy ring if she had a Confederate officer living in her home? In truth, this did nothing to slow her down. She created her own Polybius Table to cipher messages and continued to spread her information via hollowed out eggs and false heels in shoes. The mansion even remained a stop on the Underground Railroad, with Elizabeth hiding escaped prisoners in her secret room upstairs while she dined with the prison Commandant downstairs.
Elizabeth was even able to set up a direct communication line with General Butler at Fortress Monroe. Through this connection, Elizabeth relayed the information that there was a move of a large number of prisoners scheduled. It was decided that Union forces would make a move to capture Richmond, while a smaller force was tasked with disrupting the transfer and freeing the prisoners. Some of the prisoners escaped, but on the whole the mission was a dismal failure. 22 year-old Colonel Ulric Dahlgreen was killed, and since his father was a well-known Rear Admiral, Ulric’s body was desecrated, buried in an unmarked shallow grave, and his prosthetic leg was kept as a trophy.
This didn’t sit well with Elizabeth, so she sent out her network of spies to find the exact location of Ulric’s body. Once found, she sent men to exhume the body, and then had it moved north of Richmond for a proper burial. All of this would have gone completely unnoticed, except Rear Admiral Dahlgren petitioned President Davis for the return of his son’s body. Davis conceded, and ordered that the body be sent north. However, when his men dug up the grave, it was empty, leaving President Davis looking rather foolish. Elizabeth waited until after the war to contact the Dahlgren family with the actual resting place of their son.