“I find myself in a Position to address you a few lines and I hope that they may find you in as good health as I am myself in.” There is nothing unconventional about this opening salutation, except that it was written by a slave to his master soon after he escaped. It is, however, unusual in other important ways: the author clearly meant to thumb his nose at his master, to demonstrate his capacity for independent action, and to assert his commitment to freedom. But this sort of communication, written so soon after an escape, ran the risk of destroying the best laid plans. That it did not says something about the person who executed what, by any measure, was a masterful plan of escape from slavery in 1853. Written by Henry W. Banks to William M. Buck, a forty-three-year-old slaveholder of Front Royal in the Shenandoah Valley of Virginia, the letter was ostensibly mailed from New York on February 15, 1853. Buck had hired Banks in 1849 from his owner, Edward W. Massey, who lived a short distance from Front Royal. Evidently, Banks had requested the move so he could be near his wife. But he may have had other plans. Less than two years after the transfer, Massey got word that Banks was planning to escape. Massey had him jailed, but Buck intervened and had Banks released, confident that the rumors were baseless. In April 1852, Massey got wind of another planned escape and this time sold Banks to a local slave trader. Again, Buck came to Banks's defense: family connections, he predicted confidently, would keep Banks close to home. To convince Massey that there was nothing to the latest rumor, Buck agreed to post a security of $800 should Banks escape before the expiration of the contract they had renewed every year since 1849. In less than a year, Banks was gone – where to no one knew. Massey was convinced that he had fled with his brother Landon and despaired of ever retaking him. His “smartness,” Massey predicted, ensured he would not be captured.