My discovery resulted in considerable reading including Hugh Rankin's overview, Peter Earle’s description of Sir Henry Morgan’s exploits, and the first hand reports of Esquemeling, Dampier, and Hakluyt. I read descriptions of Captain Cromwell by William Bradford and John Winthrop, two major chroniclers of the first half of seventeenth century colonial America. And then I came upon a reference to a little known, unpublished manuscript entitled Mercurius Americanus, which described a 1642-45 voyage to the West Indies carried out under the command of Captain William Jackson. Captain Cromwell was one of his officers. I ordered the manuscript from the British Library and painfully deciphered the mid-seventeenth century script. After this extensive reading I felt ready to attempt a characterization of Captain Cromwell, which I hoped would ring true.
Cromwell was reportedly born in London, England. in 1617. Winthrop states that “he was ripped out of his mother’s belly, and never sucked, nor saw father nor mother, nor they him.” He first came to colonial America as a seaman while still in his teens. He participated in at least one voyage to the West Indies in the 1630s. Circumstantial evidence suggests that he was married to Anne ____ by 1639 or 1640.
In the 1642-45 voyage Captain Jackson left England for the West Indies with a commission from the Earl of Warwick, giving legal status to acts of reprisal against Spain for the latter’s aggressive acts toward England. The possession of a “commission” had the effect of defining an aggressive act toward another country as “privateering” rather than “piracy,” a distinction hardly of importance to the victim. Jackson left England with three ships, arrived at Barbados, and set about recruiting additional men from Barbados and St. Christopher’s Island, outfitting three pinnaces and hiring a merchant ship. The total number of men was finally 1100, 640 being common seamen and 460 being officers.
The men were divided into land forces and sea service. In all likelihood Captain Cromwell was part of the original group that left from England although there is a possibility that he joined the group in the West Indies. It appears that he was part of the land forces - at least there is no reference to his being a captain of a ship. Summarizing the expedition is difficult due to the fact that new ships were “acquired” from the Spanish, ships were sunk, and ships became separated. From the Barbados the expedition sailed along the northern coast of South America, invaded the Island of Margarita but secured little “purchase” -- the euphemism applied to items of value such as gold, silver, and jewels. The inhabitants had been forewarned of the arrival of the ships and had moved their wealth and themselves elsewhere (an occurance which repeated itself a number of times during this expedition).
From Margarita the expedition moved on to Maracaibo where the purchase was more significant (e.g., capture of four ships, 10,000 pieces of eight for returning the town to the inhabitants). After Maracaibo the ships sailed to the south coast of Hispaniola to ‘‘revictual,” then sailed westward to Jamaica where on 25 March 1643 the Spanish capital, Santiago de la Vega, was captured and not returned to the residents until the Spaniards “should deliver us 200 Beaves and 10,000 pound weight of cassavy bread for the victualing of our ships besides 10 Beaves everyday for present expence till our departure and 7000 pieces of eight.”
The expedition left the area 21 April 1643, returned to Hispaniola, sailed south to Santa Marta on the South American continent (now in Colombia), then back to Jamaica, and west to the Cayman Islands, arriving 4 June 1643, where much discontent among the men began to be expressed. At that point the merchant ship was allowed to leave the expedition with 200 men aboard, including Sergeant Major William Rous. One of the reasons for Rous’s departure was a “private dislike of our General’s intent for the Bay of Honduras.” The author of Mercurius was often critical of the Spaniards and praiseworthy of the British, especially Major Rous. There seemed to be only one British officer whom the author did not like --Captain Thomas Cromwell.  He blamed Cromwell for leading the expedition on a wild goose chase up and down the coast of Central America hunting for but never finding a town of San Pedro that was supposed to be loaded with wealtb. Cromwell is described as “pretending,” “specious,” and “professing himself an expert pilate for the partes.” Reading between the lines I have the impression that the author sided with Captain Rous in not wanting to include the Bay of Honduras in the expedition’s itinerary and carried some resentment that the ‘‘General” would be persuaded by the self-confident 25 or 26-year-old Cromwell to pursue a venture in that particular area. In all likelihood Cromwell was searching for San Pedro Sula, Honduras, which lies thirty miles from the coast in fact, was destroyed by the pirate Francois L’Ollonais in 1660.
With historical perspective more favorable adjectives such as determined, undaunted, and courageous might be just as appropriate to describe Cromwell as “specious” and “pretending.” Trying to further understand the author’s bias, we can speculate that Cromwell may have had a kind of irritating, self-assured, immodest quality about him.
After criss-crossing the Caribbean and plundering the west coast of the Yucatan, Captain Jackson resolved ‘‘to put a period to this voyage" and the expedition arrived back in England in 1645. The next known reference to Cromwell is made by Winthrop and Bradford in their respective journal entries for 1646. By then Cromwell has “inherited” from Captain Jackson the Earl of Warwick’s commission, was captain of three ships and eighty men, and had accumulated considerable “purchase” on the open seas. The ships were forced by a strong northwest wind into Plymouth where they stayed four to six weeks. Bradford described the men as “lustie…very unruly….who, after they came ashore, did so distemper themselves with drinke as they became like madd-men; and though some of them were punished and imprisoned, yet could they hardly be restrained; yet in the end they became more moderate and orderly.”
Bradford further gives an account of how Cromwell in his effort to discipline a particularly aggressive seaman “gave him a blow with the hilts (of his rapier); but it light on his head, and the simal end of the bar of the rapier hilts peirct his scull, and he dyed a few days after….but the captaine was cleared by a counsell of warr.” Winthrop describes the same incidents at Plymouth but in somewhat more positive vein - e.g., indicating that the poor people of Plymouth benefitted from the seamen’s presence, describing how Cromwell made an effort to have the wound of the seaman “searched and dressed” but that the seaman refused, and how Cromwell provided a formal funeral for the deceased seaman.
After Plymouth Cromwell went to Boston where he presented to Winthrop an elaborate sedan chair which had been taken from a Spanish ship and was alleged to belong to the Mexican Viceroy. While in Boston Cromwell could have stayed in the finest facilities but elected to lodge “in a poor thatched house” because, according to Winthrop, the host had entertained Cromwell “when others would not, and therefore he would not leave him now, when he might do him good.” After Boston Cromwell returned to the West Indies, was out three years, took “sundry prises” and returned rich to Massachusetts. He died during the summer of 1649 when he fell from his horse and landed on his rapier hilts. Bradford implies that Cromwell may have obtained his just deserts (“ther might be something of a hand of God herein”), and I wondered if that same quality in Cromwell that irritated the author of Mercurius also bothered Bradford.
Cromwell’s will was short and probably hastily prepared after his injury. He left five pounds to his daughter, ten pounds to “Goodwife Sherman,” five pounds to “Goodwife Spaule,” six bells to the Town of Boston, and the remainder of his estate to his wife, Anne. Although there is no solid evidence of Anne’s parentage, Cromwell’s will raises the possibility that she was the Anne listed as daughter of Richard and Elizabeth Sherman and sister of Alice Sherman who married Thomas Spaule.
The Cromwells had only one child, Elizabeth, conjectured to have been born around 1640. She first married Richard Price on 18 August 1659. They had Thomas b. 22 July 1660, Joyliffe b. 2 March 1662, Elizabeth b. 10 February 1664, and Richard b. 26 March 1667. The older Richard died in 1674. The younger Elizabeth (i.e., Cromwell’s granddaughter) married James Townsend of Boston. The older Elizabeth (i.e., Cromwell’s daughter) married her second husb Isaac Vicers, between the period of 1674 and early 1680s. They had a daughter, Rebecca, who married Captain Samuel Binney of Hull on 11 Nov. 1701.
I am enjoying my possible descent from Captain Thomas Cromwell. Hopefully, I have presented sufficient material to indicate that he was a complex person who does not neatly fit into the stereotype of a pirate, that he had human foibles but also some admirable qualities. The study of piracy and privateering is a fascinating way to study history, and perhaps like the Son of a Witch Society the descendants and other students of pirates should also formally gather together and share their knowledge. The reader is invited to write me directly for further genealogical information on Cromwell as well as for a bibliography: 12 Lawyers Walk, Asheville, N.C. 28801.