John B. Wills, Sr. was born around 1740 and died in 1822.  His ancestry is unknown but it is likely that his family had been in Maryland for several generations (see the Wills Family in the Colonial Period).  He lived his entire life in the Port Tobacco Creek valley as a successful farmer and man of business, leaving a large family across Charles County, as well as two sons who moved to Louisiana.

He married Anne Livers (daughter of James Livers and Mary Saunders), heiress to part of Green’s Inheritance in that same area.  Anne was born not long before 1746, because on April 28th of that year was recorded a gift of her grandmother: “I, Prudence Green, of Charles Co., widow, for the natural love have for my granddaughter, Anne Livers, daughter of James & Mary Livers, & for divers other good causes, I have given Anne 3 Negro children, viz, Priscilla, James, and Henrietta, to be delivered to her at age 16 or day of marriage. …. If my granddaughter Anne dies before age 16 and unmarried, the Negroes return to me. Signed Mar 26, 1746 – Prudence (+ her mark) Green. Witn – Walter Hanson, John Neale.”  (Charles Co. Md. Land Record Liber Z#2, 1744-1753; page 96).

Most of the Wills’ social connections and those of their children were with related Catholic families of the Port Tobacco parish: Green, Semmes, Digges, Neale.  Their awareness of social connections can be seen from the fact that all eight of their surviving children apparently bore the names of ancestors or close relatives. They were particularly close with the family of Ignatius and Mary Doyne Semmes (a cousin of Anne Livers Wills), and their children continued that friendship. The Wills’ daughter Elizabeth Brent Doyne Wills was named after another cousin in that family.

John B. Wills, Sr.’s date of birth around 1740 can be approximated from the ages of his children and the fact that he was already an adult in 1764 when he witnessed his friend Ignatius Semmes’ will.

He is well documented in the census and public events of the Revolutionary period:

1775 Durham Parish East Hundred
1777 Md. Red Books: Private, 26 Battalion, Capt. Wm. McPherson’s Co, Chas. Co. Militia
1778 Charles County, Port Tobacco East Hundred, Oath of Fidelity
1778 Charles County, Port Tobacco East Hundred, list of adult men

Beginning with 1790, a federal census was conducted every decade in accordance with the constitution of the newly formed United States.  These censuses give the name of the head of the household (other household members are named beginning in 1850) and the numbers of other residents by gender, age group and free/slave status.

In the 1790 household of “John Baptist Wills” are recorded 2 males (aged over 16), 3 females, and 4 enslaved persons. Presumably, these are the head of the household, his wife (?), one son (JBW Jr.?) and the two unmarried daughters.  The census lists his oldest son Joseph Ignatius as head of a separate household, with no other males.  So where are the three youngest sons?  His wife may already have died (she is absent from her mother’s will in 1794) and perhaps the smaller children are being raised by another relative.

In the 1800 Census lists “John B.Wills, Senr” Wills with males 1 (10-16),  2 (16-26), 1 (over 45); females 1 (10-16) and  2 (16-26);  12 enslaved persons (a significant increase from the 1798 survey of Maryland slave owners which records him with only 4).  If we make some tolerance for underestimating ages, we can now account for the three younger sons and two unmarried daughters and one unknown female (perhaps a white housekeeper).  Among the neighbors listed on the census are several of his family’s social circle:  Hamiltons, Greens, Spalding, Smith, and Clements.

By the 1810 Census, when he is about 70 years old, the household of John B. Wills, Sr. is considerably simplified: besides the himself, there is only one male (aged 26-45) and one female (aged 16-26) and 8 enslaved.  At the time of the 1820 Census, he is the only white person on his farm, with 9 enslaved persons of various ages, of which 6 persons were “engaged in agriculture”.

He lived very close to Mt. Carmel Monastery, where his daughter and daughter-in-law asked to be buried, and it is likely that his family often worshipped there, although they would also have been involved with at the main Jesuit parishes in Pomfret (west across Port Tobacco Creek) and St. Ignatius Church on St. Thomas Manor (6 miles south rising above the Potomac River).

His farm was conveniently located just 4 miles north of Port Tobacco, the business and legal center and only real town in Charles County.  His land and business dealings over the years are recorded in various deeds and court cases. Particularly well documented is a loan of $1200 he made around 1817 to Samuel Chapman, for the vestry of Port Tobacco Church, because it was involved in a case that went to the Court of Appeals.

He lived a long life until about age 80, when he died intestate in 1822. The inventory of his estate, valued at $3,326.82, was sworn on 2 Dec 1822.  The administrators of his estate were his son Joseph I. Wills and grandson William Thompson.

John B. Wills Sr. had married well, arranged good marriages for his children and handled his own affairs well enough to provide for his eight children, and he left an estate larger than he had begun with — all this during a time when Southern Maryland was in economic decline and many had moved further west or south.

John B. Wills Sr. and Anne Livers had eight adult offspring, who are clearly named and given various bequests in the 1794 will of their grandmother Mary Livers. They are apparently listed in order of birth (more information can be found on their separate pages):

1) Anne Prudence Wills (bef. 1770-1820) m. James Thompson (d. 1795)

She was named for her mother Anne and her mother’s grandmother, Prudence Cooper Saunders Green. Anne’s son William acquired Araby, the estate of George Mason’s wife, and descendants lived there for a century.

1.1) Justinian Wills, died young
1.2) Col. William Thompson (1790-1853), m. Mary Grace Davis
1.3) Col. Francis Thompson (1791-1876), m. Charlotte H. Johnson
Militia captain in 1813.  Daughter Anna m. cousin Charles H. Wills
1.4) Anna Maria Thompson

2) Mary Helena Wills (bef. 1770-1832), single. She was named co-executor of the will of her grandmother Mary Saunders Livers, who bequeathed her enslaved men and women. Accordingly, she is probably the Mary Wills of Port Tobacco East in the Maryland slave owners and superintendents list of 1798. Little is known of her except from her will in which she requests to be buried at Mt. Carmel and makes bequests to her various nieces and nephews.  She calls herself “Mary H. Wills” in her 1832 will but is called “Mary Aliana Wills” in the old copy made of her grandmother’s will.  Presumably, her name was Mary Helena Wills (with capital “H” confused a ” A+l””), and she was named after her mother’s grandmother Helena Gordon Livers (d. 1757/1762), who was still alive in her mother’s teenage years.

3) Joseph Ignatius Wills (c.1770-1836) m. Anastasia Hatcher

Their descendants lived on Cobb Neck and were buried at Holy Ghost Church

3.1) William Alfred Wills (c. 1811/2-1870) m. Dorothy Rosella Hamilton
3.2) Mary Emily Wills (1813-1863) m. Zachariah Lloyd
3.3) Lucy Ann Wills (c.1814-1850s) m. William T. Campbell
3.4) Joseph Ignatius Wills, Jr. (1817-1880) m. Elizabeth H. Norris
—  Their daughter Mary Ann Wills m. her cousin Charles A. Neale
—  Their daughter Mary Henrietta Wills m. her cousin Richard Earl Wills
3.5) Elizabeth Wills (born 1825)
3.6) Dr. Francis H. Wills (1826-1855), m. Mary O. — (not to be confused with his cousin Dr. F. R.Wills)

4) John Baptist Wills, Jr. (c. 1773-1844) m. 1) Ann Carey Floyd, 2) Ann Jarboe

His descendants lived at Johnsontown, Preference and the Bel Alton area

4.1) Dr. Francis Reed Wills (1803-1872) of Preference, married twice, had 16 children
4.2) Elizabeth Ann Wills (c. 1815-1854) m. James Neale
4.3) William Wills (c. 1816-after 1880)
4.4) Alexander Wills (1819-1844)

5) Elizabeth Brent Doyne Wills (c. 1775/77 – ?) m. Mr. Clements

5.1) Mary Elizabeth Clements (1814-1877) m Dr. John H. Digges at Johnsontown in 1838.  Their five children including daughter Mary Clements Digges who m. cousin Francis Hughes Wills.

6) William Livers Wills (c.1776/79- 1819) m. Mary Thomas

He went to West Feliciana, Louisiana around 1815 and soon married and then died there.  Two children: 6.1) John F. Wills m. Eliza C. Glover,  and 6.2) Julia Ann Wills m. Calvin Dorris Bowman, Sr.

7) Frederick Wills (1780-1825) m. 1) Teresa Hamilton, m. 2) Ann Catherine Green

In the War of 1812 militia, then went to Grand Coteau, La. as part of a small migration of Southern Md. Catholics (including Mudd, Gardiner, Green relatives). The numerous descendants of his son Justin Wills (m. Magdeleine Burleigh) still live there today.

8) Charles Wills (1782-1852) m. Jane Green.

In the War of 1812 Militia. Lived near Pomfret. No living descendants with the Wills name.

8.1) Charles H. Wills (1824-1896), m. his cousin Anna Thompson
They and their children lived at Araby until the 1940’s.
He served as consul to Managua, Nicaragua under Pres. Cleveland.

8.2) F. Leo Wills (c. 1827-after 1870), corporal in Confederate Cavalry
8.3) William X. Wills (c. 1830-1865), Georgetown College, Harvard Law School
8.4) Mary Jane Wills (c. 1828-1851) m. J. Thaddeus Brawner