[2] Working in collaboration with the engraver Amos Doolittle, Earl drew four battle scenes that were made into pro-Revolutionary propaganda prints.
In 1778, he left behind his wife and daughter and escaped to England by disguising himself as the servant of British army captain John Money.
After his return to America, he made portraits of Timothy Dwight, Governor Caleb Strong, Roger Sherman, and other prominent men.
In September 1786, while living in New York City, Earl was imprisoned for failing to pay his personal debts.
Even while in jail, he drew portraits of his visitors, friends, and family of the Society for the Relief of Distressed Debtors.