BIRTH: He died on 1 December 1690 in Drowned off Cape Breton, Nova Scotia, Canada, at age 62 . The cause of death was In the French and Indian War, Captain Stephen Greenleaf, Lieutenant James Smith, Ensign William Longfellow, Sergeant Increase Pillsbury, William Mitchell and Jabez Musgrave were cast away and lost on an expedition against Cape Breton.
"The expedition under Sir William Phips, consisting of thirty or forty vessels, carrying about two thousand men, sailed from Nantasket on the ninth day of August, 1690, but did not arrive at Quebec until the fifth day of October. Several attempts were made to capture the town, without success; and, tempestuous weather having nearly disabled the vessels and driven some of them ashore, it was considered advisable to re-embark the troops and abandon the enterprise. On their way back to Boston, they encountered head winds and violent storms. Some vessels were blown off the coast, and ultimately arrived in the West Indies. One was lost upon the island of Anticosti, and several were never heard from. Capt. John March, Capt. Stephen Greenleaf, Lieut. James Smith, Ensign William Longfellow, and Ensign Lawrence Hart, of Newbury, Capt. Philip Nelson, of Rowley, and Capt. Daniel King, of Salem, were among the officers commissioned for service in the expedition to Canada, under the command of Sir William Phips."
Footnote from the Diary of Samuel Sewall, p. 335, which states as follows: "Twas Tuesday the 18th of November (1690) that I heard of the death of Capt. Stephen Greenleaf, Lieut. James Smith, and Ensign Wm Longfellow, Sgt. Increase Pilsbury, who with Will Mitchell, Jabez Musgro, and four more were drowned at Cape Britoon (Breton) on Friday night the last of October."
He came to America with his father and resided in Newbury, Massachusetts, until he was drowned off Cape Breton, 1 Dec. 1690. In 1651, he married Elizabeth Coffin, the daughter of Tristram and Dionis (Stephens) Coffin, Sr., of Newbury, Massachusetts, by of whom he had ten children.
9 June 1677, Stephen Greenleaf in full communion with the Church Christ at Newbury, Massachusetts: "The 22, 3, '77. These may certify the much honored General Court sitting in Boston the 23d of the 3, '77, that the persons whose names are underwritten, being in full communion with the church of Christ in ---, and otherwise qualified according to Law, desire that they may be admitted to the freedom of this Commonwealth."
Stephen Greenleaf, appraiser to will of Benjamin Swett. His widow, Hester, administrator.
Stephen Greenleaf married by Commissioner Dalton, 31 March 1678/9? (Widow Swett 1678/9). He left a will on 25 December 1668 in Massachusetts. He began military service in 1670 in Newbury, Essex County, Massachusetts, appointed Ensign of the Company at Newbury. He was also known as Capt. Stephen Greenleaf Sr. He was a member of the First Congregational Church. He was made a freeman on 23 May 1677 in Newbury, Essex County, Massachusetts. His will was proven on 12 February 1691 in Massachusetts.

• Married: 13 Nov 1651 in Newbury, Essex Co, MA

1. Stephen GREENLEAF Jr. b: 15 Aug 1652 in Newbury, Essex Co, MA