- After receiving his A.M., he entered into the service of the Earl of Lincoln and served in several capacities under the care of Thomas Dudley, steward at Sempringham, Lincolnshire. In 1627 Dudley resigned his post and left to live in Boston, Lincolnshire, England. Simon succeeded to his position. Eventually he became the steward of the Countess of Warwick.
Simon served as an assistant to Gov. Winthrop at the time of the crossing, though he was only 27. On 23 Aug. 1630 he was elected the first Secretary of the Colony. In which office he continued until 1644. He was the seventh member of the First Congregational Church of Charlestown and Boston. In 1631, his family and the Dudleys, moved to Newtowne, now Cambridge. In 1635, both families moved to Ipswich, staying there until 1644. In 1644, he was one of the pioneers of Andover where he built the first mill on the Cochichawick Brook. They settled in North Andover.
Four years after his wife’s death, he married again. He was chosen Deputy Governor of Mass. In 1678 and elected Governor in May 1679 until 1686 when the charter was annulled.
With the establishment of the Dominion of N.E., he stepped aside, refusing to be a Counsillor. After the rebellion against Sir Edmund Andros, Simon was appointed President of the Council of Safety in charge of arresting Andros. He was again elected Governor, a post he held until 1692 when Sir William Phips arrived from England as the first Royal Governor. Simon served as his assistant.
A boulder on High Street in the town of Ipswich carries a plaque and marks the site of the Bradstreet home.
-- HISTORY of CAMBRIDGE, MASSACHUSETTS 1630-1877, PREFACE, p. 73:
Bradstreet, Gov. Simon [(Rev. Simon bp. Hobling, Co. Lincoln, 18 Mar. 1603] one of the founders of Cambridge, 8, 32; res. E. cor. Harvard Square and Brighton [Boylston] Street, XV, 9, 27; Assistant 6 n., 23, 459; real estate of, Pelham's Island 174; rem. to Ipswich then to Andover, Boston, and Salem, m. (1) in England, Anne Dudley (Gov. Thos.) m. (2) sister of George Downing, 498, signs pardon of John Pratt, 27; selectman 1634-5, 21, 462; opposed to witchcraft trials, 116; com. to consider duty to king, 69; elected pres. Council of Safety 77-111, 113; sent to England, 71; brought forcibly to Council House 110; signs petition to Andros 111; Palfrey's opinion of, 114; share in pales, 11; agreement for cart way, 20; d. at Salem, 27 Mar. 1697, a. 94, 498
Savage says: SIMON, Cambridge, Ipswich, Boston, was a few yrs. at Andover, and spent his latest days at Salem, after Sept. 1695; b. in Mar. 1603, at Horbling, in Lincolnsh. s. of Simon, a min. it is said, bred at Emanuel, Cambr. Univ. enter. there 1617, and matricul. 9 July 1618, as a sizer, had his A. B. 1620, and A. M. 1624, came in the fleet with Winthrop 1630, chos. an assist. 18 Mar. bef. and so cont. by Ann. elect. 48 yrs.; secr. 23 Aug. 1630 to 1636; dep.-gov. 1673-8; gov. 1679 to 1686; and again after the rising against Sir E. Andros 1689-92; d. 27 Mar. 1697. By his first w. Ann, d. of Gov. Thomas Dudley (a lady of some celebr. for poetical talent, wh. d. 16 Sept. 1672, at Andover), m. at the fam. hist. in Geneal. Reg. IX, 113, says, a. 1628, wh. to me seems a yr. or two earlier than prob. tho. we kn. it was bef. the Apr. embark. in 1630, had Samuel, H. C. 1653, bef. ment.; Dorothy, wh. m. 14 June 1654, Rev. Seaborn Cotton; Sarah, wh. m. 1. Richard Hubbard of Ipswich, and 2. capt. Samuel Ward; Simon, b. 28 Sept. 1640, H. C. 1660 Hannah, wh. m. 3 June 1659, Andrew Wiggin of Exeter; Mercy, b. 1647, wh. m. 31 Oct. 1672, maj. Nathaniel Wade; Dudley, 1648, bef. ment.; and John, 22 or 31 July 1652, bef. ment. His sec. w. Ann, wid. of capt. Joseph Gardner, d. of Emanuel Downing, younger by more than thirty yrs. wh. he m. 6 June 1676, d. 19 Apr. 1713, aged 79. [2, 4, 5]