Jessup was a native New Yorker who fled to Canada when his property was confiscated by the Rebels.
He raised a Loyalist Regiment consisting mainly of displaced New Yorkers.
Jessup accompanied Burgoyne to Saratoga where he and his men were sent to Bennington to obtain supplies.
John Stark had other ideas and Jessup's Unit was badly mauled at the battle.
Jessup escaped and eventually made his way back to Canada.