I want to give you a word of warning, this article contains spoilers for the musical Hamilton.  

Like millions of others during lockdown, I joined in the Disney+ fanfare and watched the musical Hamilton for the first time using their platform. I can’t pinpoint when I became obsessed but, long story short, my entire Spotify On Repeat is now consumed by the Hamilton soundtrack. I’m absolutely helpless. To give a succinct synopsis of the musical, it depicts US founding father Alexander Hamilton’s rise up from poverty. It details him becoming George Washington’s right-hand man during the revolutionary war, then his achievements following independence as Treasury Secretary, and his subsequent downfall. After having watched the musical and listened to the album many times, I have come to the grand conclusion that Hamilton is the most insufferable character in his own story and I am going to attempt to convince you of the same.


First of all, can we discuss how unnecessarily self-assured Hamilton is? As early as the second song ‘Aaron Burr, Sir” Hamilton explains that he “may have” punched a member of university staff because “he looked at me like I was stupid, I’m not stupid.” How can he be so sure? In addition, a line from the next song “My Shot” also exhibits this same overconfidence. When he introduces himself to John Laurens, Hercules Mulligan and Lafayette, Hamilton brags “don’t be shocked when your history book mentions me.” This claim is somewhat reminiscent of the classic X Factor contestant who proudly announces they will win the entire show and get a big record deal before absolutely butchering a Shania Twain song.

Gives Bad Advice

Furthermore, Hamilton gives terrible advice in high stakes situations. His son, Phillip, finds himself preparing to duel with one George Eaker later in the musical, over the latter’s speech attacking Alexander denoting him as a ‘scoundrel’. Rather than say the obvious and acknowledge that he is a scoundrel, or encourage Phillip to back out from such a silly reason to fight, Alexander instead advises his son to shoot in the air during the duel rather than to take a shot at George directly. His son then takes his advice which leads to his untimely death. Not only that, but Hamilton continues this by following his own advice two years later in a duel with Aaron Burr – where he does the exact same and is killed by Burr. One would hope he’d have learned his lesson the first time.

Bad Friend

Alexander Hamilton is also an untrustworthy friend. One of his best friends from the very beginning, Lafayette, brings help from France to support American troops and orchestrates a great deal of the Battle of Yorktown. During the song ‘Yorktown’ the two discuss what they will do once the war ends. Lafayette explains that if they win, “I go back to France, I bring freedom to my people if I’m given the chance” to which Hamilton replies “We’ll be with you when you do.” This was a total lie. Later in the play during ‘Cabinet Battle 2’, Hamilton goes back on his promise and argues in favour of neutrality in the French Revolution. Did he forget Lafayette? Has he an ounce of regret?


Of course, I cannot finish this list without reminding you Hamilton is an adulterer. Following years of marriage to Eliza Schuyler, he begins an extended affair with Maria Reynolds. Furthermore, he fails to halt the cheating when her husband finds out, and he is then extorted for thousands of dollars. Then, rather than being honest with his wife, Hamilton hides the affair for many years – until he is accused of embezzling US funds. In reaction, he publishes ‘The Reynolds Pamphlet’, which explains he did not misuse government funds; he was using his own money to pay his mistresses husband. This then leads to the breakdown of his marriage. If only his regard for his wife’s feelings were as meticulous as his paperwork.

To conclude, it is clear that Alexander Hamilton is indeed a scoundrel as George Eaker proclaimed. It is enough to make you wonder whether his story is even worth telling. I must acknowledge that it likely is – he did achieve a great deal, from his military career to establishing the US national bank to later founding the New York Post. Does he deserve to be the central character of this story though? I’d argue no – the most significant reason that history books mention him at all is thanks to his wife Eliza, who tirelessly worked to have his achievements recognised following his death. She preserved his writings, she raised funds for the Washington Monument, she spoke in favour of abolitionism. She also pursued her own goals, such as co-founding the first private orphanage in NYC which she is “proudest of”. Perhaps, it would be prudent to change the musical to “Eliza Schuyler – An American Musical.” That would definitely be worth watching as arguably, she is the true hero of this story.