William later wrote that the plan felt like “a desperate leap for liberty.” That description is exactly right. Everything that could go wrong was attached to factors they could not control: a conductor who asked the wrong question, a former acquaintance on the platform, a hotel clerk who required a signature they could not produce, a slave-catcher who had seen their descriptions.
There was also a fundamental problem of literacy. Neither William nor Ellen could read or write. For an enslaved man, this was the law’s intention — literacy was dangerous, frequently prohibited, a route to self-documentation and self-liberation. For their escape, it created a specific logistical crisis: the hotels and steamship registries they would encounter required guests to sign their names. Ellen could not sign a name she didn’t have in a hand she couldn’t control.
Ellen solved this problem herself. “I think I have it,” she reportedly said, in the account William would later record. The solution was the arm sling. If her right arm was immobilized — if she appeared to be an invalid gentleman whose injury made writing physically impossible — she could ask other parties to sign on her behalf without arousing suspicion. The invalid framing did double work: it explained the arm and gave them a plausible reason for traveling to Philadelphia, where they could say she was seeking medical treatment.
The rest of the disguise was built piece by piece. William purchased items separately, in small transactions, to avoid drawing attention to any single unusual purchase. A pair of green spectacles. A top hat. A second-hand white beaver cap. A poultice to be tied under the chin and around the head — this served to hide the smooth, unbearded jaw that might betray a person presenting as a man. Ellen cut her hair short at the back. She made the trousers herself.