Sharon Doliante's book, I believe, has the most solid analysis of the origins of Richard Cheney, immigrant.His first land patent was dated 1658, but during the preceding half dozen years Maryland was in civil war between Lord Baltimore's people and Puritans from Virginia, and not much was recorded, so the 1658 date could reflect something that actually happened earlier.
Richard Cheney and Charity his wife were given 100 acres for bringing themselves into Maryland.In June 1652, the deal was changed from 100 acres per person to 50, so we know Richard and Cheney arrived after June 1652.However, years later, their oldest daughter Elizabeth gave her age in court testimony, and her birthdate calculates back to this time period.We know Elizabeth was born in Maryland about 1652, but she was not born when Richard and Charity arrived or they would have gotten an extra 50 acres for Elizabeth as well.So it's quite possible Charity was pregnant with Elizabeth when they arrived and Elizabeth was born soon after in 1652.
Sharon Doliante thinks Richard immigrated from Virginia because he settled among the Puritans in Anne Arundel County and later wrote his will in the home of Col. Burgess who had been a Puritan leader.But it looks like Richard was more busy farming than politicking or warring because his name doesn't show up in those records.
His first properety was Cheney's Hill which was excavated in the last 10 years because a developer wanted to build houses there and they had to give the archaeologists a crack at things first.Among other artifacts they found a small statue of King Charles, which made them wonder if Richard was a royalist rather than a Puritan.Some mysteries remain to be solved.
But for those of us who like me are descended from Richard, that's as far back as we can go at this point.There are all kinds of Cheneys across the pond waiting to be connected to, but there is nothing documented yet that can connect us to them.