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991. Ensign Nathaniel LEONARD746,747 was born about 1766 in Middleboro, Plymouth Co., MA.2 He died about 1828 in Ontario, Canada. He was buried in Cataraqui United Church Cemetery, 965 Sydenham Road, Kingston, Ontario, Canada K7M 3L8.748 Referred to as Nathaniel Leonard 2nd and Nathaniel Leonard, Jr., inMiddleborough VR's. (e.g. at birth of son Nathaniel and son Simeon).There was another Nathaniel Leonard in Middleborough (his uncle), whichwould have made him the younger of the two and hence "jr." or 2nd.

He was an Ensign in the Mass. Militia by the time of the birth of sonSimeon in 1803, according to Middleboro VR's. He was also referred to asEnsign Nathaniel Leonard in the Middleboro Gazette of 2/26/1859:2 for thepurchase of the herring privilege at Assawaset Brook in 1797.

In the 1790 Census, there is no Nathaniel Leonard listed inMiddleborough. He would have been married by then and had a daughter.There is a Nathaniel Leonard, household of 3, one male 16+ and 2 female,listed just over the border in nearby Raynham near Zephaniah Leonard andothers who were involved with the ironworks there. This leads to theconjecture that Nathaniel was working at the ironworks there and obtainedhis knowledge of their construction and operation.

In the 1800 Census, Nathaniel Leonard 2nd is listed with a number ofother Leonards in Middleborough. Nathaniel 2nd must have been bornbetween 1756 and 1774, as he is listed in the "males 26-44" column. Thefamily consisted of 2 males under 10 (Nathaniel and Abraham), 1 female10-15 (Betsy), and one female 26-44 (Betsy). There is a NathanielLeonard with a family of 8 also living in Middleborough in the 1800Census, but gone by the 1810 Census (died or moved?).

There are several Nathaniel Leonards who served in the RevolutionaryWar. Several were definitely not this Nathaniel, viz. Nathaniel ofPlymouth who served as a seaman, Nathaniel of Raynham who served as aprivate and a corporal, Nathaniel of Taunton who served as a major andlt. colonel. He was possibly the Nathaniel Leonard, private, who servedin Capt. Elisha Barney's company and Capt. Benjamin Rider's company inalarms at Rhode Island in 1776, but he was probably too young to serve atthe time.

Nathaniel Leonard: "He got into trouble over a horse and skipped off toCanada," according to genealogist Elisha Clark Leonard in his manuscript(p. 172) tracking 7 generations of Leonards. ECL has sparse informationon Nathaniel, including birth date. Same is true for other children ofJoseph. GML's charts include the same information as ECL's, but tracethe descendants further.

There is in the Court of Common Pleas 1796 to 1807 the following cases:"25. Nathaniel Leonard, II, Gentleman (Middleborough) v. Josiah Leonard(Westport Forgeman). Case, that on 13 September 1798 pltf. casually lost'a brown stallion horse to the value of forty dollars,' which the deft.found and 'converted to his own use,' to pltf's damage of $50. Defaultby deft. Judgment for $40 and $6.99 costs. Fully satisfied." Nathanielwas the plaintiff and the victim of the pilfered horse. He was not a"horse thief," and the incident does not appear, contrary to Elisha ClarkLeonard's description, to have been the cause of his "skipping off toCanada."

James Sproat Esq. (Taunton) and William and Zachariah Porter (BothMiddleborough Traders) attached Nathaniel Leonard (MiddleboroughMillwright). Case, on note dated 10 January 1794 for £10.2s.5 1/2d.payable on demand to pltfs. "by the Name of William Porter and Co." withinterest till paid. This establishes Nathaniel's profession -- amillwright -- which would have classified him as a "gentleman."

Other cases: "12. Isaac Leonard (Middleborough housewright) v.Nathaniel Leonard II, Gent. (Middleborough) and Timothy Wood(Middleborough, yeoman). Case, on five notes dated 13 April 1801 eachpayable with interest, 4 notes for $20; and 1 note for $3.66. Default bydefts. Judment for $88.74 and $10.59 costs." "41. Isaac Morton(Middleborough Yeoman) v. Nathaniel Leonard II, Gen. (Middleborough).Case, on note dated 9 January 1801 for $75 with interest. Default bydeft. Judgment for $78.67 and $9.23 costs." "53. Hushai Thomas, Gent.(Winthrop) v. Nathaniel Leonard II, Gent. (Middleborough). Case, on twonotes: dated 5 August 1801 for $20 with interest, on demand; and dated17 November 1801 for $15 with interest, on demand. Pltf. said thatrefusal to pay was to his damage of $70. Default by deft. Judment for$26.89 and $9.50 costs. Appealed by deft.*" "Court allowed $2.25 toWilkes Wood Esq. on a complaint of Joseph Bump v. Nathaniel Leonard IIand Leonard Sears." Leonard Sears was Nathaniel's brother-in-law,married to Nathaniel's sister Abiah Leonard. "Thompson Baxter, Gent.(Bridgewater) v. Nathaniel Leonard, Gent. (Middleborough). Case, as perwrit.* Default by deft. Judment for $323.03 and $12.76 costs (CommonPleas, 1806)." He seems to have been involved in a significant number ofcases in the early 1800's.

There are no cases after 1806. Was this when he "skipped off to Canada?"

In Canada he married Jennet (Jennette, Janet, Mary Jane) McDonell(McDonald?). Her father was a Loyalist of Edwardsburg Township,Grenville Co. Earliest record in Canada is an application for land fromJennet Leonard, his wife, dated 21 January 1809, requesting 200 acres ofland, apparently promised to those who were of age (21) and would settlethere. Nathaniel and Jennette had 8 children, of which Joseph was theoldest. Apparently, Nathaniel died at a fairly early age (winter of1828-29), and Joseph at age 18 took over providing for the family. Adeposition from a neighbor in 1850 says that he died intestate and thatJoseph Helmer Leonard was his eldest son and heir at law.

An obituary appearing in the Canadian Christian Advocate, Hamilton,Ontario, dated July 4, 1877, about Nathaniel's son, Rev. Joseph HelmerLeonard, says: "His father was a citizen of Massachusetts and went toCanada to erect large mills, being a very skillful builder of suchmachinery. Joseph pursued this occupation up to the age of 18, when hisfather died and left him and his widowed mother in charge of sevenyounger children." It is possible Nathaniel Leonard visited Canada inthe years before he "skipped off."

During the War of 1812, Nathaniel served as a private in a troop ofprovincial light dragoons from June to December 1812 and possiblylonger. He may have been a part of Lt. Col. "Red George Mcdonnell'stroops who captured Ogdensburg in 1813 (in retaliation for the Americanattack on Gananoque in 1812?). His friend, Joseph Helmer, after whom itis postulated his son was named, died during that attack. He died beforeclaiming his entitlement of land for military service; and his sonJoseph, as his heir, made that claim in 1850 (Ont. Archives RG 1, C13,vol. 133, p. 88). The War of 1812 must have cut into Nathaniel's millbusiness, as in 1812, 1816, and 1817 he applied for and was granted alicense to keep an inn at his home in Edwardsburgh, the 10 pounds for hislicense being his tax for the year.

His borrowing of money and being sued for nonpayment continued inCanada. A sampling of court cases: From Archives of Ontario,Johnstown District Court Case Files. RG22-416-0-1296 Year of 1825Trueman Raymond sues Nathaniel Leonard for non-payment of promissory notedated 6 April 1821 to the amount of £9-11-3. This debt is settled bycourt order on 11 Feb 1826 in the amount of £10-0-6.
RG22-416-01686 Year of 1826: Rice Honeywell sues Nathaniel Leonard fornon-payment of promissory note dated 1 March 1820 to the amount of£13-5-0. This debt is settled by court order on 6 Feb 1826 in the amountof £13-10-8. This debt wasincurred in the Township of Augusta, perhapsexplaining why he was not found in Edwardsburgh in 1820.RG22-416-0-994-container 7 filed under the 1824 date. In the DistrictCourt – As of May term 1823 – District of Johnstown Paul McMillan puts inhis place, Jonas Jones his attorney against Nathaniel Leonard in a pleaof contract. The said Nathaniel Leonard in person at the suit of thesaid Paul McMillan in the plea aforesaid. Nathaniel Leonard was summonedto answer to Paul McMillan in a plea of Contract: and thereupon the saidPlaintiff by Jonas Jones his Attorney
complains: For that whereas the said defendant on the sixth day of Junein the year of our Lord one thousand eight hundred and twenty-two atBrockville was indebted to the said Plaintiff in the sum of threepoundsfifteen shillings of lawful money of the Province of Upper Canadafor goods wares and merchandize sold and delivered by the said Plaintiffto said Defendant at his request: and: for labour and services done andperformed by said Plaintiff at his request. Money had and received bysaid Defendant to the use of said Plaintiff: and money paid laid out andexpended by said Plaintiff for said Defendant at his request: and beingso indebted the said Defendant in consideration Thereof, then and therepromised the said Plaintiff to pay the same, but which he now refuses: tothe damage of the said Plaintiff of forty pounds and therefore he bringsthis suit. And the said defendant in person comes and defends thewrongand injury and says that he cannot deny the action of the said Plaintiffnor but the said Plaintiff hath sustained damages to three pounds sixteenshillings and one penny halfpenny of lawful money of Upper Canada: andhereupon the said Plaintiff prays judgment and his damages soacknowledged, together with his costs and charges by him about his suitin this behalf expended be adjudged to him. Therefore it is consideredthat the said Plaintiff do recover against the said Defendant his damagesaforesaid to three pounds sixteen shillings and one penny halfpenny inform aforesaid acknowledged and also three pounds four shillings and fivepence halfpenny for his said costs and charges by the said court now hereadjudged to the said Plaintiff and with ------ (here there are twoillegible words): which said damages costs and
charges in the whole amount to seven pounds and five pence halfpenny. Andthe said Defendant in (balance of sentence, only a few words, is lost ina crease of the document.) In the Johnstown District Court Paul McMillanPlaintiff and Nathaniel Leonard Defendant.

I confess this action and that the Plaintiff hath sustained damages tothe amount of three pounds sixteen shillings and one penny halfpennybesides his costs to be taxed. In default of payment on the first day ofnext term, the Plaintiff shall be at liberty to enter Judgment and sueout execution and levy the said sum of money, together with costs taxed,Sheriff’s poundage and all other incidental expenses. As witness my handthis 2^nd day of April 1823 (signed) Nathaniel Leonard." An additionaldocument was included in the docket that showed the expenses incurred bythe person who served the writ on Nathaniel Leonard. I did not considerit of enough interest to copy it. It did have, however on its reverseside a notation “”Leonard lives near Spencers Mill, Edwardsbg.”

The first iron smelting in this part of Canada occurred at an ironworksat Lyndhurst in 1801. It is unclear whether Nathaniel had any part inits operation. It started under Wallis Sunderlin of VT and lateroperated by James Schofield, who apparently left to return to New York.It operated until 1811, when it was destroyed by fire. Nathaniel islisted as a gentleman and millwright in a court suit in MA; his fatherwas a refiner of iron.

Nathaniel was a Presbyterian, his wife Jennet was raised a RomanCatholic, and their children were left free to pick their own religiousaffiliation. They were buried in a United Church cemetery.

Information on this branch of the family courtesy of Lisa Leonard andEric Bowler via the Internet April 4 to 8, 2002. Eric says theinformation about the Leonards came to him from Molly Leonard, who wasliving on Taiwan in 1999. Eric also supplied documentation concerningNathaniel. In particular, the annual local census and tax assessmentrolls for Edwardsburgh provide detail as to the family from 1810 to 1832,when the family disappears from the Edwardsburgh rolls. It would appearthat Nathaniel was travelling a large part of the time, one would guessdue to his work, and that the family rented a house near town whileretaining most of the acreage granted to Janet/Jane.

OneWorldTree does not list Nathaniel among children of Joseph Leonard andAbigail Raymond, but research there seems incomplete on this branch ofLeonards. Both Middleboro and Taunton VR's were destroyed by fire in the1800's and have been partially reconstructed from grave and other records.

See notes on Betsey Bryant for info on their marriage. They wereapparently in some sort of contact after he went to Canada, for she wasaware of when he died.

Check Russ Waller, Frontenac Co. Loyalist Families, Kingston, ON December1996, p. 158.

Ensign Nathaniel LEONARD and Betsey BRYANT were married on 20 Mar 1788 in Middleboro, Plymouth Co., MA.2,749 Betsey BRYANT (daughter of Jesse BRYANT and Mercy SHAW) was born on 24 Mar 1770 in Middleborough, MA.750 She died on 28 Feb 1858 in Cazenovia, New York.751 There were four Elisabeth or Betsy Bryants born in Middleborough aboutthe right time to have been Nathaniel's wife:

- Betsy Bryant, daughter of Jesse Bryant and Mercy Shaw, born March24, 1770 (Middleborough VR, CD# 203, p. 297)

- Elisabeth Bryant, daughter of Amos and Margaret Bryant, bornOctober 31, 1770. Elizabeth Bryant, "pauper 8 yrs," died October 15,1843, in Middleborough, age 73 (born 1770), daughter of Amos.

- Elisabeth Bryant, daughter of Seth and Sarah Bryant, born July 13,1772

- Betsy Bryant, daughter of Micah Bryant and Margaret Paddock, bornJanuary 26, 1773 (Middleborough VR, CD #203, p. 271)

Various genealogists have various Betsy Bryants marrying NathanielLeonard. A Bryant genealogy by Albert Scott Bryant lists Betsy, daughterof Micah and Margaret, as marrying Nathaniel. A. S. Foley has Elizabeth,daughter of Amos and Margaret, as marrying Nathaniel. Hadaway on his website has either Betsy by Jesse and Mercy or by Micah and Margaret asmarrying Nathaniel. Two Betsy Bryants are in Middleboro VR's, Jesse andMercy's, born 3-24-1770, and Micah and Margaret's, b. 1-26-1773.Elizabeth Bryant, dau. of Amos and Margaret, b. 10-31-1770, is also there(She died 15 Oct 1843 in the Middleborough Alms House). In none of thecases is the husband shown, although it is for some women in the records.

A Betsy Bryant of Freetown and William Howland of Middleborough marriedDecember 9, 1790 (bans published November 14). Elisabeth Bryant marriedNathaniel Leonard, Jr., March 20, 1788 (bans February 29), but theMiddleboro VR's don't list her parents. An Elisabeth Bryant marriedJosiah Manley of Middleborough August 16, 1744 in Brockton. And anElisabeth Bryant married Israel Cook October 15, 1795, in Boston. Noneof these records list the parents of the bride.

"Hard copy" (as opposed to the CD versions) of the Middleborough VR liststhe intentions and the marriage of Nathaniel Leonard, Jr., and ElizabethBryant as February 29 and March 20, 1788, respectively (Middleborough VR,Vol II, Book 2, Part 2, p. 111, p. 150).

The History of the Town of Middleborough, Massachusetts, 1669-1905 byThomas Weston (Boston: Houghton-Mifflin, 1906) includes an appendix withthe membership of the First Church of Middleborough. On page 673, recorddated August 23, 1807, the date she became a member of the Congregation,member no. 686, Betsey Leonard, w. Nathan'l, m. 1788, o. Bryant, fa. 637,d." Betsy Bryant Leonard, who married Nathaniel in 1788, was member#686, and her father, Jesse, was member #637.

Until I find evidence otherwise, I believe Betsy Bryant, the daughter ofJesse Bryant and Mercy Shaw, was the wife of Nathaniel Leonard.

This Betsy had a brother, Abraham Bryant, son of Jesse and Mercy, who wasborn July 22, 1786 (Middleborough VR, CD 203, p. 298), and died September30, 1796 (Records from the Nemasket Cemetery, Middleborough, CD 203, p.2; Middleborough VR, CD 203, p. 271). It may be just a coincidence thatBetsy and Nathaniel named a son Abraham Bryant Leonard in December 1796.

A Betsey Leonard is listed in the 1820 Census in Middleborough as head ofhousehold of two, both women.

There was a Betsy Leonard, 80, living in the household of Rev. LewisLeonard, husband of the late Betsey Leonard, in Cazenovia, NY, in the1850 Census. Could it be that Betsy Bryant Leonard didn't die in 1807before/after Nathaniel skipped off to Canada? The Rev. Lewis Leonardmaintained ties with the Middleboro area, with his arrival noted in theMiddleboro Gazette 10/21/52:3 and his death 12/05/1856:2. The death of aBetsey Leonard, former Middleboro woman at age 88, is noted in theGazette 3/13/58:3. This appears to have been our Betsy, who was born in1770. "In Cazenovia, N.Y., on the 28th of February 1858, Mrs. BetseyLeonard, aged 88 years. Her native place was Middleboro. In 1827 shecame to this place with her son-in-law, the late Rev. Dr. Lewis Leonard,in whose family she found a home soon after the early death of herhusband. Having outlived all her children, she spent the last nine yearsof her life in the family or Mr. H. J. Weed, with her grand-daughter, andwas kindly cared for to the last. Mrs. Leonard was distinguised forquietness, industry, and good will. She was a blessing to those withwhom she lived, and a blessing to the Baptist Church, of which she was amember. A firm believer in Christ, the fruits of righteousness wereapparent to the last. Pleasant are the memories of this aged disciple."(Cazenovia Republican).
Ensign Nathaniel LEONARD and Betsey BRYANT had the following children:






Abraham Bryant LEONARD.



Simeon LEONARD747,752 was born on 23 Jan 1803 in Middleboro, Plymouth Co., MA.66 He was born on 23 Jan 1803. He died on 16 Aug 1803 in Middleboro, Plymouth Co., MA.66 He died of "languishment," according to Middleboro records (MiddleboroDeaths, Gen. Society of Mayflower Descendants, 1947).



Nathaniel LEONARD.

Ensign Nathaniel LEONARD and Jane Jennett MCDONELL were married about 1808 in Edwardsburgh, Ontario, Canada. Jane Jennett MCDONELL (daughter of John MCDONELL) was born in 1787 in Edwardsburgh, Ontario, Canada. She died on 6 Jul 1858 in Kingston, Ontario, Canada.753 She was buried in Cataraqui United Church Cemetery, 965 Sydenham Road, Kingston, Ontario, Canada K7M 3L8.748 Variations on the name: Jennet McDonell, Jane McDonald. Jennett is indocuments related to land grants; Jane is name on her tombstone.

From Upper Canada Land Grants RG1, C14, Volume 3, page 37: Lot 17,concession 3, Township of Osgood, was granted to Jennet Leonard as thedaughter of a United Empire Loyalist. Acording to Ontaio Archives landrecrods GS3714, reel 576 (Osgood Township), she sold it on 15 March1832. This was just weeks before son Joseph's marriage, so it may havefinanced her move to Kingston and perhaps helped Joseph and his bride.

The Osgood land records show the following grants to children of JohnMcDonell of Edwardsburg: Lot 17, Jennet Leonard, lot 21 Ann McDonell,lot 25, Catherine McDonell, Lot 30-32 Allan McDonell. Ensign Nathaniel LEONARD and Jane Jennett MCDONELL had the following children:



Rev. Joseph Helmer LEONARD.



John Duncan LEONARD.



Unknown LEONARD was born about 1813.



Rev. Dr. Raymond Henry LEONARD.






Catherine LEONARD.






Nathaniel James LEONARD.