Captain John Dent came into Maryland about 1658 with Thomas Dent who claimed land rights in 1663 for his transportation, and in that year John Dent witnessed a conveyance of William Hatton to Thomas Dent. The year previous or 1662 he witnessed the last will and testament of William Hewes who bequeathed his entire estate to William Hatton of William and William Dent of Thomas. In 1695 he employed William Dent of Thomas his attorney to institute legal action against on Lemaister. In those years it is therefore evident that he was in close association with Thomas Dent and was a freeholder of age.