John Bailey, ADS, Baltimore County [MD], June 25, 1759. 1p, 7.75 x 12.5 in. One hundred pounds of Earnest money to be paid to Charles Carroll Esq. & Company by John Bailey. Charles Carroll of Carrollton was a representative to the Continental Congress from Maryland and signer of the Declaration of Independence (and longest surviving signer). He also became Maryland's first US Senator.

There was a John Bailey who was Lieutenant Colonel of the 2nd Massachusetts Regiment, but he seems to have been a resident of the Boston area rather than the Baltimore or Annapolis areas, with which Carroll was associated. It is unclear if this was the person who would go on to lead the Massachusetts Line from the earliest days of the war.

Uneven toning, repair on verso to one fold.