I am descended from Elizabeth Samuel and Benjamin Lawless.They were married in Charles County, Maryland (I don't know why!) on 28 June, 1784.
Ben and Elizabeth appear to have moved to Mercer County, Kentucky, ca. 1786--about the same time as some of her siblings, with their families, made a similar move.
Benjamin Lawless was a lawyer, and apparently handled the administration of the estate of his father-in-law Thomas in 1796, even though he (Ben) was a documented resident of Kentucky by that time.
From correspondence with another Samuel/Samuell researcher, as well as independent research performed for me by a professional researcher, it seems "likely" to me that this Thomas Samuel was the son of Thomas, son of Anthony, Sr. of Caroline County--all this more by a process of elimination of other likely candidates than by any kind of smoking-gun document.
I would be happy to discuss this further with you.Please contact me directly at firstname.lastname@example.org.