Obadiah Cookson was born on 1 Feb 1709, son of John and Rachel (Proctor) Cookson of Boston, Massachusetts. He was the second son and fourth child of eight children. On 26 Apr 1737, he married Margaret Smith, daughter of Thomas Smith also of Boston. They had two children, John, born 10 April 1738 (and our ancestor) and Margaret born 29 May 1740, both in Boston. Sadly, Obadiah's wife, Margaret, died on 19 Jan 1742 leaving him with two small children, age 3 and 20 months.
Obadiah needed a new wife so perhaps he was a bit hasty to remarry. On 22 June 1743 he married a second time, Faith Waldo, daughter of Cornelius Waldo. She was thirty, he was thirty-four. They had three children, Samuel, Elizabeth and Lydia.
Obadiah was a grocer with a shop on Fish Street in Boston, "at the sign of the Cross X Pistols". He posted numerous advertisements in the newspapers of the day. Waldo Lincoln in "Genealogy of the Waldo Family, 1902, says he was "a very eccentric man" and a "persistent advertiser, in that respect being ahead of his times." In a confirmation of a mortgage dated 1 Sep 1756, he was called, "a Person thought to be of unsound mind." At some point he was accused of advertising a house for sale that he didn't own.
Faith left Obadiah in 1748, according to Lincoln Waldo. Their daughter, Lydia was born 28 Jul 1749, so she likely left late in 1748 while pregnant with Lydia. She left because "the marriage had proved unhappy". It must have been very unhappy indeed because women didn't do that in 1748 Boston. She never went back to him. She was supported by her brother, John Waldo, and in 1763 an act was passed by the Massachusetts Legislature allowing her to sell land that was left to her by her father. this act, dated 24 Feb 1763, states that Faith "still under covert with Obadiah Cookson...the said Obadiah and Faith having lived separate for divers years and continuing to do so."
Obadiah didn't take well to this turn of events. In Waldo Lincoln's book her prints "a singular notice" that Obadiah placed in the Boston Gazette on 28 Jun 1748 (note the dates don't make sense as Lydia was born Jun 1749 unless there was a brief reconciliation between Obadiah and his wife.) In this notice he catalogs his problems with his wife, Faith, saying she ran away from him, threatened to run him into debt, had a feather bed taken out of the house without his permission, took papers, money, china, books, keys out of his house and declares that he will not be responsible for her debts unless she returns and "manifests her steady disposition to behave as a wife ought by Law and Reason to do..." If she does come back he promises to "proclaim with great Cheerfulness her good Deeds" as he does now her "Evil ones". He also mentions that Faith's brother, John Waldo, violently assaulted him. This notice apparently created quite a stir because the next day the Gazette published a notice that they would no longer print "Advertisements of Elopements" unless signed by a Justice of the Peace!
Obadiah died on 17 Nov 1764 in Pepperell, Massachusetts where the record lists him as a "stranger from Boston". He was 55. Perhaps he was there for business. Faith died in Boston on 8 Nov 1784, age 71. Their son, Samuel became a prominent citizen in Boston but their daughters never married. Perhaps they were discouraged from doing so by the experience of their mother!