While he did nothing openly to oppose the Confederacy, he aided in a secret way the escape of his sister and niece. Simon was not absolutely certain of the success of the Union armies, and to insure the freedom of his sister and niece, he made use of the first opportunity, which soon presented itself. As is well known, there was before the war what was known as an "Underground Railway" for the escape of slaves to the free States and Canada. This was nothing more nor less than agents sent out by Northern Abolition societies to abduct slaves, thousands of whom escaped in this manner. It was on this account that the "Fugitive Slave Law" was passed by Congress, on which there was the test case before the Supreme Court in the slave, Dred Scott, said court sustaining the law. One of the Northern societies at this time sent an agent South as a spy, and to abduct any slave or slaves that he could entice away. This agent made his way to Colonel R.'s plantation, over which Simon was foreman. He cautiously made known his business to Simon, who welcomed and secretly harbored him. This agent was joined two days after by an escaped Union soldier from the Confederate prison at ----. This was a happy and unexpected meeting between the spy and soldier. What they did had to be done quickly and secretly. If they were captured the spy would be executed and the soldier reincarcerated in prison. Simon also had enemies on the farm who would give him away to the nearest provost marshal if it was known that he was harboring these men. Simon arranged for an immediate conference at night, when it was agreed upon that they were to take Elsie and Octavia, and for two stout negro men to go also, to alternately carry Octavia, who by this time was a year and a half old and full grown for her age. Simon spotted two stout negro men whom he thought he would have no trouble in getting to go along. But the very first one he approached, named Henry, bluntly and insolently refused. Simon told him then that if he ever divulged it he would handle him roughly. Henry left, telling him to "go on 'bout his biziness; that he fixin' tu git hisself in trubble." He had no trouble in getting the next he approached, whose names were Jim and Jack.