Dexter at some points attempted to settle down and become a small town lawyer and politician. Even in a small town, however, his Brown education could not net him business. As for his political career, the highest position he ever acquired was ironically that of tax assessor, and even that did not last long.
The only project to ever leave a lasting effect on the nation was his first major enterprise after his return to America. Andrew Dexter Sr. passed away in 1816, and the most valuable possession he left his son was a pack of land scrips, essentially money used only to buy federal land. In Milledgeville, Georgia, he used these scrips to purchase a swath of land in the newly-acquired Alabama territory, including a bluff on the bend of the Alabama River.
After an arduous journey, Dexter surveyed his new investment and named it New Philadelphia, claiming that it would become the capital once Alabama entered statehood. The fledgling settlement, called Yankee Town by its neighbors, would eventually combine with those competitors to incorporate as Montgomery. The town would become the state’s fourth capital in 1846, but Dexter himself would never see his only successful gamble pay off.
A transference of land from 1827. Instead of investing in the real estate he acquired, Dexter preferred to sell the land when he was in need of money, which was often. Courtesy of the Montgomery County Archives.
In 1812, New York had recently adopted more lenient bankruptcy laws, and the homesick Dexter family used the opportunity to re-enter the country and attempt to settle their financial situation. Dexter and both sides of the family had nearly emptied their respectable resources investing in the Exchange, leaving them with at most modest funds.
Dexter would spend the rest of his life attempting to reclaim the wealth and status he and his extended family had lost to the skyscraper. However, each of these endeavors was marked by failure.
In Nova Scotia, Dexter had attempted to invest in the mining of gypsum, but he could make no headway in the business. Dexter had a persistent interest in land investment in the second half of his career, investing in multiple locations in Alabama and Texas, but none of these kept him solvent. He attempted to build a series of lumber mills along Catoma Creek, a swift-flowing tributary of the Alabama River. After a dubious deal to acquire the land and paying for the mills' construction, a flash flood immediately wiped them all off the map before any work could be done.
A plan for the city of Montgomery from 1846, courtesy of the Alabama Department of Archives and History
On the Frontier