WINTHROP, Stephen (1619-58), of James Street, Westminster, and Boston, Massachusetts

Stephen Winthrop was born at the family home at Groton in Suffolk, but in March 1630, at the age of 11, took ship for America with his father and the rest of the family, to found the colony at Massachusetts Bay.11Winthrop Pprs. i. 235; ii. 222. From his adolescence, Winthrop shared the godly fervour of his parents. At the age of 14 he was thrown into despair at his sinfulness, ‘and especially for his blasphemous and wicked thoughts, whereby Satan buffeted him, so as he went languishing daily’; but through prayer and self-examination ‘he came at length to be freed from his temptations, and to find comfort in God’s promises’ and was received into the Boston congregation as a true believer.12Winthrop, Life and Lttrs. ii. 109. His dramatic conversion, as much as the importance of his father, seems to have recommended the young man to the colonists. Admitted freeman of the Massachusetts Bay Company in December 1636 (at the age of 17) in due course he was elected as the recorder of the new town of Boston.13Recs. Mass. Bay, ed. Shurtleff, 372; Winthrop, Life and Lttrs. ii. 368. From 1637 he was active in settling legal disputes, or protecting the landed interests of the Winthrops; and members of the extended family (including Emmanuel Downing and Richard Saltonstall) relied on him as the manager of their properties in New England.14Winthrop Pprs. iii. 337; iv. 65, 71, 87, 174, 306. Winthrop also took charge of trading ventures, upon which the survival of the colony depended. In March 1638 he took a ship to England to buy household goods and equipment, and in the following winter commanded a flotilla bound for Bermuda.15Winthrop Pprs. iv. 21, 87, 93. His cousin by marriage, the puritan divine Hugh Peter, was so impressed by Winthrop that when planning a visit to settle differences with the Dutch in 1639 he asked if Stephen could go with him.16Winthrop Pprs. iv. 113. On a further trip to England, in 1642-3, Winthrop acquired a suitably godly wife: Judith, sister of Thomas Rainborowe*.17Winthrop Pprs. iv. 418; Firth and Davis, Regimental Hist. i. 179.

In the winter of 1644-5 Winthrop planned to return to England for an extended period, leaving his affairs in the hands of his half-brother, John Winthrop II. Immediately on his arrival in March 1645, Winthrop was confronted by Alderman William Berkeley and other London citizens owed money by the Boston colonists, and especially by John Winthrop I. As this legal dispute dragged on, Stephen Winthrop found himself short of money – a situation not helped by a disastrous trading mission to Tenerife in the summer of 1645, where prices were too low to allow a profit.18Winthrop Pprs. v. 13, 20, 28, 69-70, 98; Coll. Mass. Hist. Soc. ser. 5, viii. 201-4. Winthrop was back in Boston by the end of the year, but, concerned that he would become a burden to his family, returned to England in the spring of 1646 to embark on a military career. His main advisers in this seem to have been Hugh Peter and the Rainborowes. In October 1646 his half-brother John told their father that Stephen ‘means to stay in England with his brother [Thomas] Rainborowe who is governor of Worcester and he is captain of a troop of horse’.19Winthrop Pprs. v. 102, 114, 147. The regiment he joined was, in fact, that of Colonel Thomas Harrison I, whose major was another brother-in-law, William Rainborowe.20Firth and Davis, Regimental Hist. i. 179. Hugh Peter assured Winthrop’s father that ‘your son Stephen doth all here by good counsel’; but Winthrop saw his change of career in religious terms, claiming in July 1647 that: ‘providence opening a way of employment in the army, I have accepted of it seeing no door open to me any else of being serviceable in my generation’.21Winthrop Pprs. v. 147, 174. Warming to his theme, he continued:

the kingdom is now upon a great turn. God is doing some great work, for when the adversaries were with all violence setting up injustice and persecution of the saints it pleased God by the army to put them to a stand … I thank God I am free in my spirit to engage in what the army hath propounded.22Winthrop Pprs. v. 174.

In the summer of 1648, Winthrop’s providential convictions were further strengthened by the success of the army against the royalists, and he served under Oliver Cromwell* when the Scots were defeated at Preston in August.23Winthrop Pprs. v. 280, 311.

Winthrop’s belief in the army as an instrument of God’s justice shows his closeness in attitude to Cromwell and other leading New Model officers. He did not, however, share the radical political and religious agenda of some of his colleagues, including his brother-in-law, Thomas Rainborowe, and his regimental commander, Thomas Harrison. The Boston congregation was Independent, not sectarian, and in 1645 Winthrop had already noted ‘great complaint against us for our severity against Anabaptists’.24Winthrop Pprs. v. 13. Thus, when Harrison’s regiment mutinied in support of the Levellers in May 1649, Winthrop did not become involved, and by the end of the year he had been rewarded for his loyalty by promotion to the rank of major.25Firth and Davis, Regimental Hist. i. 184-5; Wanklyn, New Model Army, ii. 50. From the autumn of 1649 until the spring of 1651 Winthrop was stationed in Wales, being ‘left with some horse to keep quiet these parts’, and he was appointed a commissioner for the propagation of the gospel there.26Coll. Mass. Hist. Soc. ser. 5, viii. 211-3; A. and O. In the summer of 1651 he was in London, among the forces defending Parliament against renewed royalist activity. In September his troop was among those chosen to escort the Scottish prisoners to the capital after the battle of Worcester.27CSP Dom. 1651, pp. 349, 351, 358, 364, 412, 424.

During this period Winthrop became increasingly restless. Although steadfast in his support of Parliament, and convinced that ‘God hath done great things here in England, Scotland and Ireland’ he repeatedly told his friends in New England that ‘I expect not to settle in England, but to return amongst you’.28Coll. Mass. Hist. Soc. ser. 5, viii. 212-3. His journey home was deferred by the onset of illness. In August 1653 Winthrop told John Winthrop II that

could I be assured of my health, I think I should come away immediately, for I have no health here, and have been this two years extremely troubled with the sciatica … my much lying in the wet fields upon the ground hath brought it upon me … it makes my life very uncomfortable.29Coll. Mass. Hist. Soc. ser. 5, viii. 214-5.

He had not recovered by January 1654, when his regiment, without its colonel (who had been cashiered in December 1653) was sent to Scotland. In May 1654 George Monck* requested new officers, stating that he had allowed Winthrop to stay in England ‘being ill and unfit to endure the field’.30Scot. and Protectorate ed. Firth, 105. Despite this, Winthrop was appointed colonel of his regiment at the beginning of September.31Clarke Pprs. v. 206. In March 1655 Winthrop was still languishing at Westminster, and contemplated resigning his commission and returning to New England, for ‘the cold weather is my greatest discouragement, and while I am here I am troubled with journeys into Scotland, which is almost as bad’.32Coll. Mass. Hist. Soc. ser. 5, viii. 216. Between November 1655 and March 1656 he was sufficiently recovered to join his regiment in the Aberdeen area, and oversaw courts martial and assisted tax collection in the region.33Worcester Coll. Oxf. Clarke MS XLVII, unfol.: 5 Nov., 3 Dec. 1655, 11, 16, 24 and 28 Jan., 6 Mar. 1656. On 10 March Winthrop was granted a pass to return to England, but his regiment continued to be garrisoned in the area, and when the parliamentary elections were held in August, he was returned for the Banff Burghs.34Worcester Coll. Oxf. Clarke MS XLVII, unfol.: 10 Mar. 1656; TSP v. 366. Although Winthrop no doubt enjoyed Monck’s support in this election, he also gained the approbation of the voters, who clearly expected him to act as their representative. On 30 August the magistrates at Aberdeen appointed an agent to attend Winthrop at Westminster, and in September issued their MP with detailed instructions on behalf of the burgh.35Extracts from the Council Regs. of Aberdeen, 1643-1747 (Edinburgh, 1872), 162; Aberdeen Council Lttrs. III ed. L.B. Taylor (Oxford, 1952), 270-4.

Winthrop’s activity in the second protectorate Parliament can be divided into two periods, punctuated by another bout of illness which he described to his half-brother as ‘a time when I was very sick, being forced to keep my chamber and house most part of this winter’.36Coll. Mass. Hist. Soc. ser. 5, viii. 217. He was appointed to five committees between September and the end of November 1656, including those for Scottish affairs and for the relief of creditors and debtors – the latter at the behest of his constituents, who had asked him to help overturn the ‘late act’ on the subject.37CJ vii. 428b, 447a; Aberdeen Council Lttrs. III, ed. Taylor, 271. He did not return to the Commons until early June 1657, although he kept abreast of events from his sick-bed, remarking on 14 April that

the great business in hand is the desire of the Parliament that his highness will take upon him the title of king. He hath refused it once and twice, and the Parliament still insist upon their votes. What will be the issue I cannot tell; but it will soon be resolved for or against.38Coll. Mass. Hist. Soc. ser. 5, viii. 217-8.

Winthrop’s apparent refusal to take sides over the issue of kingship may have been disingenuous. On his return to the Commons in June he aligned himself with the army interest, which had been violently opposed to the crowning of Cromwell from the very beginning. He joined the leading army interest MP, Captain Adam Baynes, as teller on two motions: in the first, on 9 June, they opposed the consideration of Lord Abergavenny’s bill – possibly to clear a path for other business; and in the second, on 15 June, they supported important changes introduced under the Additional Petition and Advice, which would overturn the concessions made under the earlier Humble Petition and Advice, and exclude former royalists from positions of trust.39CJ vii. 552b, 557b. Opposition to the Humble Petition may also have influenced his intervention in the debate (on 24 June) on the oaths to be imposed on MPs under the new constitution, saying that ‘it seems unuseful, incongruous and unreasonable that a people that are not trusted with anything, should be under any obligation to perform a trust to themselves’.40Burton’s Diary, ii. 293. As in 1647, Winthrop was unwilling to place too much power in civilian hands, especially as he regarded the army as the true instrument of divine providence.

Winthrop’s sudden burst of activity in the summer of 1657 continued until the new year of 1658, when he attended the second sitting of Parliament, and on 21 January he used his influence with George Downing* and others to try to secure the right to hold malt market for his constituents at Aberdeen.41Aberdeen Council Lttrs. III, 303. In April the Aberdeen council still relied on Winthrop, telling its agent that to take advice from the colonel whether ‘there be any hopes of obtaining or doing any good for the town’.42Aberdeen Council Lttrs. III, 312. Soon afterwards, however, Winthrop was again struck down by sickness, and this time he would not recover. In May 1658 he wrote his will, and by June was seriously ill.43Coll. Mass. Hist. Soc. ser. 5, viii. 245. He died shortly afterwards, leaving his property in London and New England to his wife and their three surviving daughters, Margaret, Joanna and Judith. He also bequeathed smaller sums to his relatives in the Winthrop and Rainborowe families, and £100 to the poor of Boston, as long as the town erected an ornate tomb for his parents in the church there. Winthrop was buried, at his own request, in the church at Groton in Suffolk.44PROB11/280/245; Waters, Genealogical Gleanings, i. 162.