From what I can piece together
Father [–?–] Spiller had at least 2 sons.
David Spiller b. about 1619, first mentioned in Northampton County records in 1643. David is mentioned in Northumberland Co., Virginia as early as 1652. He married the widow of John Dennis between 1653/4 and 1657. David dies October 1658 at the age of thirty-nine. His will lists sons John and Swanson [OR son John Swanson] and step-sons Richard, Pasco, and John Dennis. He also mentions his niece, Susan Holling. A Nath’l Holling does the appraisal of his estate.
a. John Spiller
b. Swanson Spiller
OR David had no sons, only step-sons.
David’s brother, [–?–] Spiller, possibly named John, had a daughter named Susanna who married a Holling, possibly Nathaniel Holling.
a. Susanna Spiller md before 1658 [–?–] Holling (possibly Nathaniel]
County Court Records of Accomack-Northampton, Virginia 1640-1645. Transcribed by Susie M. Ames. 1973. Charlottesville: University Press of Virginia.
p. 351 “It is ordered by this Court that William Berryman shall within tenn dayes satisfy and pay the quantity of 1166 pounds of tobacco and caske to put it in and alsoe two payre of new shoes two payre of stockings and one lockrum shirt unto David Spillar his assignee with Court Charges or els.”
p. 366 “Know by all men that I John Waltom of the Countye of Northampton doe promise to save harmless Mr. William Berryman from an execution of David Spillar the order of the Court whereupon the execution was granted beareing date the 23th day of February 1643.”
p. 366-367. On February 10, 1644, it was “thought Fitt by this Court…that the said John Waltham shall satisfye and pay the said debt…unto…David Spillar.”
p. 440 “It is ordered by this Court That David Spiller shall have satisfaction for two paire of Irish stockings 1 shirt and 4 barrells of Indian Corne out of the estate of William Berryman deceased hee having made it appere dew for his wages upon oath.
The agreement was dated 16 July 1651, witnessed by W. Clairborne and David Spiller, and recorded on 20 September 1652.
The Northumberland Oath 1652, J Mottrom – 1941
1652 David Spiller signed oath of loyalty to Commonwealth of England
“Wee whose names are subscribed doe promis & Ingage our selves to be true & faithfull to the Commonwealth of England as it is now established without King or house of Lords”
also signing Wm Medcalfe
Northumberland County records, 1652-1655 : containing abstracts from Court order book no. 2, 20th Sept. 1652-20th Oct. 1655, Record book no. 14, 20th Sept. 1652-20th Aug. 1655, Fleet, Beverley
p. 27 Court order book no. 2 20 May 1653 p. 14
John Barnes agt. Mr Charles Ashton David Spiller on jury to decide this case whereby Barnes says that Ashton accused him of getting his maid w/ child. Maid was by this time dec’d. Apparently Barnes proved that he was not the culprit.
p. 36 Court order book no. 2 Nov 21st 1653
Joseph Wicks agt David Spiller Spiller owing Wicks 200 lb. tobo. “for worke done by the said Wicks his servant for him the said Spiller by the testimony of Tho Brewer”, Spiller is ordered to pay forthwith.
p. 45 Court order book no. 2 26 Feb 1653/4 p. 45
Colo Mottrom agt David Spiller “Whereas x x John Dennis Senr doth owe unto Mr Tho Speke 330 lbs tobacco x x the Court doth order that David Spiller with the widow and Adm x x of the said Dennis shall within 10 days make payment. x x”
p. 53 Court order book no. 2 23 November 1654 p. 28
“David Spiller is appointed constable for great Wicocomocoe and it is ordered that he take his oath before a Com’r there.”
p. 59 Court order book no. 2 20th August 1655
David Spiller gave a deposition in the case of Henry Mayes agt Capt Richd Budd and stated he [David] was “36 yeares or thereabouts”. He made his mark. dated 28th June 1655
In 1653/4 he apparently got to drinking a couple of times and made nasty remarks about other men’s wives that got him into trouble – but just recording above as proof he was there.
Virginia Colonial Abstracts, Volume 12, Beverley Fleet, p. 612
Spiller, David. Will. Entry badly damaged but this perfectly clear “I give my whole estate to be equally devided between my sonnes Jno Swanson Richard Dennis Pasco Dennis Jno Dennis excepting one cow called Florence – which I alsoe give – my youngest son Jno Dennis”. “I give unto Susanna Holling my Brothers childe” a cow. Tobacco to James Magregory. Wit Tho Gaskins, Jno Taylor. Appraisal of estate follows. This headed “by Nathaniel Holling”. Dated 21 8ber 1658. 15.11
So, does this mean he has sons named John, Swanson, Richard Dennis, Pasco Dennis, and John Dennis? Or Jno Swanson, Richard Dennis, Pasco Dennis, and John Dennis?
Virginia Colonial Abstracts, Vol. XIX, Northumbria collectanea, 1645-1720, Fleet, Beverley
p. 36 [Dennis], Richard, Pasco [Paschall], and John referred to as “my sonnes” in the will of David Spiller 21 Oct 1658. 15.11 [will was probated 21 Oct 1658]
p. 57 Thos Gaskins witnessed David Spiller’s will
p. 80 Nath’l Holling did appr. of David’s estate. Probably his brother or brother-in-law.
I would say not his brother or his brother-in-law but his nephew-in-law who married Susana Spiller.
p. 81 Susanna Holling referred to as “my brother’s child” in David’s will.
Virginia Colonial Abstracts, Volume 12, Northumbria collectanea, 1645-1720, Beverley Fleet, p. 605
Seagrave, Robert deceased. His inventory appraised by Jno. Spiller, Francis Gray, John Delahey, and Robert Cole. 20 March 1649/50. 1.48
It looks like this John may be the mentioned brother of David Spiller.