Why’s Alexander Jr a black sheep?
Alexander Hamilton Jr.
Well, “black sheep” is a wording only I seem to use. No one in the family ever called him that, obviously, but it’s the most efficient way to describe how Alexander Hamilton Jr. ended up positioned. But when I call him a black sheep I mean two related things: (1) he didn’t live up to the standard of charisma/leadership/spectacle that his father projected, and (2) he made life choices and kept a temperament that generated friction with his siblings—especially his younger brother James (who, to be fair, seemed to be a dick to all his siblings). Alexander Jr. sometimes looks defensive, self-interested, or simply out-of-sync with the household ideal. Those are not the same accusation, but they feed each other.
First, the bare facts (because every good rant needs a stage): Col. Alexander Hamilton Jr. (b. 1786-d. 1875) was one of Elizabeth Schuyler-Hamilton and Alexander Hamilton’s children, educated at Columbia, a lawyer, a soldier in the war of 1812 era, and later a man who managed property, politics, and a very complicated family legacy. He is, by every standard biography, an active adult who did important things—public office, legal work, purchases of property, and so on. Like most of his siblings, he even met Abraham Lincoln when he was still young!
The period immediately after 1804 is the silent hinge in the Hamilton family’s history. Eliza was in shock and debt. James was sixteen; John was thirteen; William and the younger sons were still minors. The family’s finances were dire, and the Schuyler side, though wealthy (mainly in land), was divided about how much to intervene. In that atmosphere, Alexander Jr. became de facto the eldest male figure in a family that could no longer afford to send every son to college or into public life. He trained in law, as his father had, but without the capital or patronage that had propelled the elder Hamilton upward. There’s very little romanticism in his early record, which is precisely why later generations forgot him. He was not considered a favorite child. He did not write affectionate letters to his family. He didn’t die dramatically or write himself into politics. He just worked.
However, after his father’s death there were concrete plans and overtures to place Alexander Jr. where a young man of promise could go places. One Mr. Higginson “readily consented to take him” into his family as a temporary boarder so the youth might become acquainted with “the respectable persons of the town” and young men “of the best reputation.” Eliza did not want Alexander Jr. to go, however. She narrowed the structural opportunities available to him at a moment when mobility and patronage mattered more than pedigree alone. There are concrete moments in the record—letters asking friends to look after him, offers from respectable households to take him in as a boarder, patrons willing to mentor him at a remove—but the decision that mattered was the household decision, and Eliza did not approve of her son leaving them alone and so far away despite how much it would mean for his future, because their family required stability now.
I do not mean to vilify Eliza. Her choice was defensible at the moment, and it probably prolonged a household that otherwise might have collapsed entirely. But history is composed of trade-offs, and this is one the family paid back later in reputational currency. Alexander Jr. emerged from those years with lawyering skill and practical responsibility, not the public network that turns ability into legacy. He became the man who kept the house running while others rewrote the story
In any case, Alexander Jr. is the one son of Hamilton who seems to have internalized the family’s duty but without the family’s myth. He became a lawyer and maintained a low political profile (more information on this later). Unlike James, who aggressively sought office and public attention, Alexander Jr. preferred to work within the system: law, land, finance. He was trained by the same legal mentors who had known his father, and that shows, like, a lot. But in the nineteenth century’s ideological split, this made him look retrograde. By the 1830s and 1840s, the Hamilton name meant “aristocratic federalism,” and the country was worshipping Jacksonian democracy. James A. Hamilton positioned himself perfectly in that context: the son of the great Federalist, converted into a Democrat, serving Jackson as acting Secretary of State (temporarily), writing memoirs about his “closeness” with Andrew Jackson. It was politically effective and socially visible, and it also rewrote their father’s image to fit James’ agenda.
Alexander Jr., meanwhile, refused to participate in that kind of reinvention. He kept to the old framework and opposed Jackson’s banking policies, sided more with Calhoun and Clay on economic stability, and kept to legal rather than populist politics.
So, pause. Who the hell were those guys?
Well, by the time Alexander Hamilton Jr. reached adulthood (the 1810s-1830s), his father’s Federalist Party was dead. The surviving Federalists had scattered:
some drifted into the National Republican and later Whig movements (supporting federal infrastructure, commerce, and a national bank),
others retreated from politics altogether, viewing the new populist democracy with suspicion.
The dominant party was now the Democratic-Republicans, but they had split into factions. The two major figures who emerged from that split were Henry Clay and John C. Calhoun.
Henry Clay (from Kentucky) and John C. Calhoun (from South Carolina) were both “War Hawks” during the War of 1812, initially nationalist Democrats who wanted to strengthen the nation. But they diverged later:
Clay became the architect of the “American System,” advocating:
a strong national bank,
protective tariffs to build domestic industry,
and federal investment in roads and canals (infrastructure). This was essentially Federalist policy in new clothes.
Calhoun, at first, was also a nationalist reformer, but over time (especially after the 1828 Tariff crisis) turned pro-states’ rights and anti-centralization. He defended nullification—the idea that states could reject federal laws they deemed unconstitutional.
Alexander Jr.’s alignment “with Calhoun and Clay” reflects a particular mid-1820s-1830s coalition: the National Republicans and early Whigs, who opposed Andrew Jackson’s populism and defended the Bank of the United States. Jackson (whom James A. Hamilton adored) was in a bitter fight to destroy the Second Bank of the United States—the very institution modeled on Alexander Sr.’s original bank. Jackson’s attack on the bank in the early 1830s symbolized the populist rejection of Hamiltonian finance. So Alexander Jr., in opposing Jackson’s policy, wasn’t necessarily a “Calhounian” in the later, Southern sense. Early on, Calhoun himself was aligned with Clay and the pro-bank, pro-infrastructure camp—until their split. In that earlier phase, Calhoun’s nationalism echoed Alexander Sr.’s centralizing ideas. That’s likely the Calhoun Alexander Jr. respected: the pre-nullification Calhoun, the one who defended national development and economic order.
In short, Alexander Jr. was functionally a Federalist without a party. He represented the post-Federalist elite—lawyers, bankers, men of property who believed in national credit, stable currency, and rule by competence rather than mass politics. Supporting Clay and early Calhoun was a way of keeping the Hamiltonian program alive under a new name. The Whigs, who would emerge from this coalition, were the ideological descendants of Federalism—constitutional centralists who distrusted mob democracy but wanted modern commerce.
It’s not that he was reactionary, it’s that he was consistent. Where James was adaptive, Alexander Jr. was principled. But the nineteenth century rewarded visibility, not integrity, so Alexander Jr. faded into the background while James wrote himself into print.
Their personal relationship was strained. We know from James’ own writings that he resented his brother’s independence and accused him, implicitly, of self-interest.
The turning point is often marked by the deaths of papa Hamilton and Federalist Dinosaur Schuyler. In November 1804, when Schuyler died, James claimed that Alexander Jr. “was away from home attending to his commercial affairs,” while James stayed to help their mother, collect rents, and manage the estate. In Reminiscences, James frames this as him bearing more burden than Alexander. That’s a recorded grievance, and given that James was only 16, it’s debated how much actual “commercial affairs” were Alexander’s responsibility at that age vs. how much this becomes a retrospective interpretation. But what matters is that in James’ memory, Alexander Jr.’s absence during that family crisis becomes a moral mark against him. Whether that’s fair or not (given how much Alexander Jr. tried to help his family), that perception becomes part of their sibling relationship.
In 1859, their sister Eliza Holly died, and there was a disagreement among the surviving brothers over how her will was to be executed. James was angered by what he saw as Alexander Jr. and his wife (also named Eliza, because these children had complexes) making excessive or unreasonable demands. One specific dispute is over letters and papers, as Alexander Jr. was accused of taking some of their father’s letters from Eliza Holly’s house after her death “without any colour of right or authority.”
Overall, James’ memoirs are full of little barbs about his brother’s supposed selfishness and lack of sympathy (accusations that say more about James than about Alexander Jr., really). The two even clashed publicly over civic matters, like the 1830s “Park meeting” in New York, where James went out of his way to appear in opposition to Alexander Jr.’s position and to make that opposition visible. James sought to define himself as the legitimate heir to Hamilton’s moral authority by contrast, by portraying his brother as aloof, unfeeling, or politically misguided. Alexander Jr. never publicly responded. That restraint and his refusal to mythologize either himself or his father, is exactly what erased him.
The irony is that Alexander Jr. probably understood James perfectly. He had seen his father’s principles turned into political liabilities in his own lifetime; he knew how easily integrity could be reframed as arrogance. Rather than chase relevance, he retreated into practice. That retreat — from politics into law, from fame into work — is precisely what excluded him from the mythology the family built around itself. The “black sheep” isn’t the rebel or the disgrace; he’s the one whose life doesn’t narrativize neatly. His existence exposes how much of the Hamilton legend is performance.
Also, Alexander Jr. was...a lawyer. He practiced before the Supreme Court of New York, worked in land and equity law, and became what his contemporaries would have called a “man of solid understanding.” But that kind of career no longer carried cultural weight in the 1820s and 1830s. The legal profession had exploded; law had ceased to be a gentleman’s intellectual pursuit and become a middle-class trade. To the public, a Hamilton who was simply a competent lawyer was no longer remarkable.
This is not to say he was entirely useless to the family; as when Eliza finally sold the Grange in 1833, it was Alexander Jr. who arranged for her new home, buying the townhouse at 4 St. Mark’s Place so she could live there with him and his wife, and with their sister Eliza Holly. He managed her finances, provided stability, and ensured she never fell into poverty as long as she lived. He didn’t publish, didn’t campaign, didn’t produce self-justifying texts, and the record we have of him is scattered—legal documents, land dealings, mentions in civic records, and the 4 St. Mark’s Place property he purchased so his mother and sister could live comfortably after selling the Grange in 1833. But that gesture alone tells you more about him than any memoir would. He was the one who ensured Eliza’s practical security while James was in Washington (despite his bold claims of being the overworked sibling when it came to the household). But nineteenth-century memory rewards narrative, not maintenance. The son who sustained the family materially disappears behind the sons who narrated it morally and politically.
By the mid-nineteenth century, as the younger Hamilton generation died off and the papers passed to John, Alexander Jr. was effectively erased from the family’s self-representation. His politics were unfashionable, his personality too private, and his career too respectable to be sensational. His death on August 2, 1875, at the age of 89, did not mark the end of an era unlike his father’s, which had a dramatic and politically charged end. Alexander Jr.’s passing was quiet and largely unremarkable in the public eye, and he died alone (given that his wife had died years prior and the couple had no children together; perhaps this was a blessing when compared to John C. Hamilton’s 14 children). He died at his residence in New York City, and his funeral did not attract the same public attention or ceremonial grandeur as those of his more politically active relatives.
In short, Alexander Jr. left no memoirs, courted no fame, and did not translate his work into the language of public remembrance. It is precisely this unwillingness to compromise, to politicize his own life for visibility or legacy, that marks him as the “other” in the family story. James, who was ideologically flexible and public-facing, ultimately fit neatly into the narrative of Hamiltonian memory: the son who carried forward the family name into the new republic. Alexander Jr., despite being competent, dutiful, and in many ways morally reliable, remained outside of that narrative because he refused the roles his family and the culture expected.
The black sheep is not always the reckless or the unpopular one; sometimes it is the person who is quietly incompatible with prevailing expectations.
...This is ignoring the fact that he:
sailed to Spain during a period of political conflict preceding the War of 1812, and joined the Duke of Wellington's forces, then fought against Napoleon’s army in Portugal.
returned to America to serve in the War of 1812.
received a commission as Captain of the 41st Regiment of Infantry in the United States Army in August 1813.
was an aide-de-camp to General Morgan Lewis in 1814 & served for one year.
took office in July 1818 as a member of the 42nd New York State Legislature for a one-year term, as one of eleven representatives to the New York State Assembly from New York City.
was appointed US Attorney for East Florida by James fucking Monroe.
was appointed to be one of three Land Commissioners for East Florida a year after that.
while there, he received the honorary civilian rank of colonel.
returned to NYC where he became successful in real estate transactions & was one of the leading names in Wall Street.
represented Eliza Jumel against Aaron Burr in court proceedings for divorce (or at least managed the discussion of their estate <- more likely option).
courted the daughter of a leading New York City merchant and almost eloped with her (Eliza P. Knox).
maintained correspondence with James Madison.
...So, you know...normal dude.