Eleven-year-old James Hubbard is sent to Thomas Jefferson's Monticello to meet the growing demand for nails by making them by hand. James doesn't want to make nails, leave his family, or his cat, Gray back at his home at Jefferson's Poplar Forest plantation. But Hubbard eventually becomes Jefferson's top nail maker -- and a man who would also rather not stay at Monticello. From young Tom Hemings, he learns all about the master of little mountain, who also happens to be the nascent country's third President. In time, James Hubbard becomes one of the reasons that Jefferson would come to call the the country's slavery issue, including the ever-present question of freeing the slaves, like having a "Wolf by the Ears."