John Chandler III of Worcester was one of the wealthiest men in colonial Massachusetts. In addition to a mansion house across from the Town Hall on Main Street, Judge John Chandler owned another 1200 other acres in Worcester, including four large farms, an orchard and several undeveloped lots. He had other real estate holdings including: two-thirds of a Charlton farmstead of two hundred acres; two lots totaling 1500 acres at Royalston; a farm with house, barn saw mill and orchard and other parcels, all totaling 3,900 acres at Murraysfield [later, Chester, Mass.]; a 100-acre parcel at Athol; and a quarter interest in a 928-acre parcel of land between Leominster and Westminster.
A staunch Loyalist, Chandler was one of six Worcester men included in an act of banishment under the penalty of death. His considerable estate valued in excess of £147,000 was confiscated, including two church pews at Worcester; 119 head of cattle; sixty sheep, thirteen horses; three carriages; and “a Negro man Servant.”
One of his sisters, Sarah Chandler, married Judge Timothy Paine [1730-1793]. Class rank determined by social standing or “dignity” of one’s family, he graduated from Harvard his rank fifth, in 1748. He served as clerk of Worcester County courts, register of probate, register of deeds, special Supreme Court justice, councilor, Worcester town clerk, selectman, and representative to the General Court from Worcester for four terms. For nearly twenty years, Timothy Paine was a Worcester selectman, Clerk of County Courts from 1751 to 1775, Register of Deeds from 1761 to 1775, Register of Probate from 1757 to 1767, members of the province’s Executive Committee from 1766 to 1773 and, for seven years, Worcester’s representative to the General Court.
A crowd of 3,000 “escorted” Paine from his house to the Worcester Courthouse where he was forced to resign and “apologize” to the people. At a disturbance in front of the County courthouse at Worcester protesting area men’s acceptance of the position of Mandamus Councillors, the wig of Judge Timothy was knocked from his head and he “refused to replace or wear it again presenting it to one of his slaves called Worcester.” Incidentally, his wife, known as “Madame Paine, was reportedly “the most outspoken Loyalist of either the Chandler or Paine families.”
At the decease of Judge Paine in 1793, the Massachusetts Spy reported that, “Long will his death be lamented and his memory venerated.” The newspaper text continued:
His mind, from nature good was improved by a liberal education, and by much experience in publick and private life. His talents were solid and useful. The many who consulted him, in their important and confidential concerns, will witness to the soundness of his judgment, and the candour and sincerity of his disposition. He was formed for every virtuous enjoyment of friendship. In the walks of social life was agreeable to all his acquaintances, and relished chaste sallies of wit and humour. In his family he blended the authority and affection of the parent with the familiarity and openness of the friend…By profession he was a Christian, and in his life religion appeared in its native form, peacable, mild, and charitable, and wholly free from that austerity and gloominess with which it is too often clothed by superstition and bigotry. At the close of his probation, in an affecting manner, he expressed his unshaken faith in the divinity of the gospel, his confidence in the mercy of God, and his hope of a glorious resurrection from the grave.
Unlike some other loyalists, he did not have to go into exile, instead spending energy managing his estate and overseeing the construction of his new home, now known as the Oaks.
With the death of Judge Timothy Paine of Worcester in 1793, for example, his former slave Worcester Winslow continued work for the judge’s estate as did Cato Walker and Jack or Jethro Gardner. Assesses at £3489, Paine’s estate confirms his wealth. A grand style of living is suggested in the room-by-room inventory of his estate, including a large silver tankard made by Paul Revere with the initials S.C., possibly indicating Paine’s mother Sarah Chandler; other items in silver bore the initials J.C., which might have been formerly owned by John Chandler, Paine’s step-father and father-in-law. In Worcester the late judge owned a mansion house with 230 acre
s as well as additional holdings of 131 acres in Worcester, including the 72-acre “Walker Pasture which Worcester Winslow lives.” Paine also owned 444 acres at Chester, in Berkshire County. Despite the judge’s demise his farm had to be worked; Cato Walker, for example, assisted in building a new barn and mending fences while Worcester was paid by the estate for six days work collecting corn and digging potatoes.
By 1794 some of his late father’s help, like Jack or Jethro Gardner have become servants of Dr. William Paine. Worcester Winslow was in the younger Paine’s employ: in October, for example, Winslow worked eight days laying a wall at Paine’s barn yard and drilling and removing rocks from Paine’s property. However, by 1798 William Paine frequently employed his father’s former slave Worcester.