18th and 19th century Salem was hardly lacking for wealthy merchants, but when Simon Forrester died in 1817, he was considered to be the richest. Born in Ireland, Simon went to school in Cork, before deciding to seek his fortune at sea. He would find himself in the employ of Capt Daniel Hathorne, who for whatever reason took a liking to the young Simon and brought him into his home. Daniel had three daughters, but no sons at that point, and may have considered Simon a potential heir to his shipping business. Simon would ingratiate himself into the Hathorne family, living with them even after the birth of Daniel’s two sons, although relationships were strained when Simon married Daniel’s daughter Rachel in 1776.
Simon would go into business with local merchant Joshua Ward, but as the Revolution continued, privateering became a more lucrative investment than simple trade. He was, on petition of the ship’s owners, commissioned as the captain of the Rover, capturing five English vessels and receiving a significant payout from their sale. During the war he would command a number of vessels, although his fortunes shifted slightly in 1782 when he was captured by the British and imprisoned in Halifax. This bout of bad luck was temporary and he was released during a prisoner exchange later that year. His next job was both safer and more lucrative: working as Elias Hasket Derby’s harbormaster.
Over the next few years, Simon focused more on business than naval conflict. He had a number of ships built, which would continue making him money, while he invested in local projects: the Salem Common, the Essex Bridge between Beverly and Salem, and the Baker’s Island lighthouse. He would buy the ‘unfinished house of Jona Ingersoll’ for himself, although his refusal to pay parish taxes on it set off a lengthy legal battle he would ultimately lose. His daughter’s did quite well for themselves, marrying merchants, doctors, and ministers, though his sons would be less successful. In 1807 his son Simon committed suicide while at sea and his son Charles would die of fits in 1816. A year later, Simon died, considered a respectable businessman by some and an eccentric troublemaker by others. What was inarguable is that he was the richest man in Salem, with a wealth of about $1,400,000. This wealth would be divided among his children, with a trust of $500 going to providing twice-yearly dinners for Salem’s poor.