In 1822 Wright was engaged by the Chesapeake & Delaware Canal Company to be the canal's chief engineer. While holding that position, he caused John Randel Jr. – who had surveyed the route taken by the canal, and who had been hired as an engineer to build its difficult eastern section – to be fired by the company. Randel sued the company for breach of contract, and tried to sue Wright as well, but that case was thrown out. In 1834 a jury returned an award to Randel of $226,885.84 (), a tremendous amount for the time. The canal company's appeals went as high as the United States Supreme Court, which affirmed the award. The company attempted to avoid paying the judgment, but the state legislatures of both Maryland and Delaware passed bills requiring the canal company to pay off its debts within five years. The huge award almost bankrupted the company.