John Montgomery, who was born ca 1732 in New Castle County, Delaware, and died 1818 in Chatham Co, NC, has long been known to have married Mary Willcox. Joseph Willcox included them in his book Ivy Mills, 1729-1866 : Willcox and allied families. Baltimore: Printed for private circulation only by Lucas Bros., 1911. Mary Willcox was a sister of John Willcox. "He [John Montgomery] lived and died near the iron works. Many of his descendants live in North Carolina."
Old Swede's Church (Wilmington, DE) has a record showing that on 22 December 1766, at Holy Trinity (Old Swedes) Church, Wilmington, DE, John Montgomery was married to married Mary Guest by Andrew (Andreas) Borrell. I am making only a minor point in stating that Mary was a widow when she was married to John Montgomery.
On pages 68-69 of the Willcox book (1911):
In connection with John Montgomery, deeds and wills recorded in Wilmington, Delaware, show that he was the son of Alexander, who was the son of John, who came to America between 1720 and 1724, and soon afterwards settled in Mill Creek Hundred, Newcastle County, Delaware. John Montgomery3 (Alexander)2 b. 1732 inherited a large tract of land in Newcastle County from his father. One of the deeds, signed John Montgomery3 and Mary his wife, dated May 2, 1771, was witnessed by Mark Willcox.
John Montogmery [sic] and his wife moved to Rowan County, North Carolina, near where John Willcox had settled.
In 1771, John Montgomery3 was senior captain at the battle of Alamance, or the "Battle of the Regulators," and was wounded at the second firing of Tryon's cannon. (Caruthers' Life of David Caldwell, p. 156.)
On Oct. 17, 1775, he was elected a member of the Safety Com¬mittee in Rowan County, pursuant to a Resolve of Congress, held at Hillsborough, August 20, 1775. (Col. Records of N. C., x, 280). He d. 2, 14, 1818, and was buried near his home, at the "Gulf," in Chatham County, N. C. His wife d. 5, 22, 1824, and was buried with her husband.
John and Mary2 (Willcox) Montgomery had issue:
1. Elizabeth, m. in succession two cousins named James Gaines.
2. Ann, m. (1st) James Brenan, and (2d) John McCoy.
3. Margaret, m. Thomas Waddell.
4. Deborah, b. 3, 3, 1770; bap. at the house of her grandfather, Thomas Willcox, at Concord, Pa., 7, 1, 1770; d. 5, 22, 1824; m. Jan. -, 1792, Gabriel Dubrutz, b. in France in 1763; d. 3, 14, 1824. They had 10 children.
[end of citation]
Cole Foot Prints by Camellia T. Denys (Provo, UT 1983) has this:
ELIZABETH COLE married Thomas Willcox, a native of Devonshire, England in 1727. They settled in Concord Township, on the West bank of Chester Creek, eighteen miles from Philadelphia. One of the first paper factories in Colonial America was established, known as Ivy Mills. Their mill furnished paper to Benjamin Franklin to publish his Almanac in Philadelphia. Up to the time of the Revolution, paper from Ivy Mills was sold to all Colonies from Massachusetts to the Carolinas. Also, for the Government Currency during the Revolution and for the issue necessary for the War of 1812. This large property and business of Thomas and Elizabeth Cole Willcox was willed to their son, MARK WILLCOX in 1767. It has passed by inheritance from father to son, and is owned by a direct descendant to this day. The Willcox were Roman Catholics, and they worshiped in a room set apart for that purpose in their Mansion House at Ivy Mills.
Thomas Willcox died in November 1779 - age 90.
Elizabeth Cole Willcox died in May 1780 - age 89.
They are buried at Ivy Mills, Concord Twp, Delaware County, Pennsylvania. Thomas and Elizabeth Cole Willcox are the parents of ten children.
John Willcox and his sister, Mary who married John Montgomery moved to Cumberland County, North Carolina in 1759. They later erected an iron works on Deep River in Chatham County, N.C. Willcox descendants scattered into Georgia, Alabama and Louisiana. The names of ELIZABETH, THOMAS and MARK have been carried down in each generation of the Willcox families. MARK, is definitely a COLE name.
So, it appears that John Montgomery married Mary (Willcox)
Gest, widow of Simon Gest.
Simon Gest of Concord, Chester Co, PA, made a LW&T on 2 Nov 1764 which was proved 29 Dec 1764. Executors: Wife Mary and Robert Mendenhall. Provides for wife Mary. To son John Gest plantation I now live on in Concord which my father bought of Mathias Kirlin containing 106 acres with 20 acres to be taken off my other tract of land and silver watch that was that of his grandfather, John Gest. To son Thomas remainder of land in Concord containing 280 acres at 21. Both son sons to be bound apprentices at 16. Son John to be brought and educated under the care of his grandfather John Salkeld until he is 16. If sons die with heirs, real estate to Uncle Henry Gest and children of Uncle James by his wife Phebe. Executors: Wife Mary and Robert Mendenhall. Witnesses: Moses Palmer, Joseph Kirlin, John Reynolds. [Wills of Chester County Pennsylvania 1748-1766, Family Line Publications, 1994.]
Old Swede's Church (Wilmington, DE) has a record showing that on 22 Dec 1766, at Holy Trinity (Old Swedes) Church, Wilmington, DE, John Montgomery was married to married Mary Guest by Andrew (Andreas) Borrell.
On 23 Feb 1787, Mary Montgomery, late Gest, now wife of John Montgomery, of Chatham County, NC, signed a release of dower. From this record it appears that Mary was the widow of Simon Gest when she married John Montgomery by 9 Oct 1768, when John Montgomery gave a letter of attorney to Mary his lawful wife. They moved to Chatham Co, NC. Much later, when Mary appeared before Edward Shippen in Philadelphia, PA, Mark Willcox witnessed. (New Castle Co, DE C-2, 38.)
John Montgomery appears to have been a widower when he married Mary. John's grandfather, John Montgomery bought property 18 May 1731 from the Penn family (William Penn had owned the land in Delaware and Pennsylvania) in Mill Creek Hundred, New Castle Co, DE, which he and wife Margaret deeded to their son Alexander on 10 May 1736. Alexander willed it in September 1746 to John. John was a minor when Alexander died. Eventually John (and Mary) sold to one Robert Montgomery, Senior who left it to wife Martha who passed it on to her daughters Martha and Jane. The land was probably near Hockessin, DE, on a main road to Newport.
This John, born ca 1732, had married one Esther surname not found who was living as of Oct 1761 when " John Montgomery of Mill Creek Hundred, in the County of Newcastle on the Delaware yeoman and Esther his Wife" cleared title to William and Daniel Montgomery to some nearby land across the line in Chester Co, PA, which Alexander and William Nevin had patented in 1744. A similar deed was made in New Castle Co, DE, to John Montgomery of Mill Creek Hundred for his inheritance from Alexander Montgomery by his siblings: Moses, William, Daniel, and Martha wife of Thomas Strawbridge, on 4 April 1771.
On 11 or 17 February 1762, Moses and Elizabeth Montgomery appeared before Alexander Johnston Esqr and acknowledged the deed to Daniel; John Montgomery appeared and acknowledged that he and his wife Esther had signed, sealed, and delivered this deed; and Andrew Oughterson and Robert Robinson stated that they had witnessed the signing and sealing.
On 6 June 1772, John Montgomery and Moses Montgomery acknowledged the deed before Alexander Johnston Esqr who recorded the probate the same day. Neither the spouse of John or Moses appeared or was mentioned, and both would have lost their first wives by then. Moses had been married to Elizabeth Roe, daughter of William Roe, at Old Swede's Church on 6 May 1757. Moses married again to Annable Robertson on 13 Dec 1764, again at Old Swede's Church; they were married by the same minister who married John and Mary in 1766.
As inconsequential as this is, my experience has been that the smallest detail may open up an unexpected trail of research.