If you could have dinner with one figure from American history, who would you choose and why? What issues would you discuss?

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12-27-15
Dinner with a Famous American
I believe that a dining companion can make or break any meal. Sharing a meal with an interesting individual can be quite wonderful and conversely, quite awful if its with someone terrible. If my dinner guest could be any famous American from history then my choices are almost endless. I would want dinner with someone who has overcome struggles and challenged authority, someone who has worked hard to get where they were, and someone who witnessed significant events in American history. The United States is blessed with many individuals who would easily fulfill these qualifications, however, if I were to pick just one to dine with then it would be Alexander Hamilton.
Today, Hamilton is probably most well known today for appearing on the 10 dollar bill. Few know anything beyond that. Many modern Americans might incorrectly assume he was once president of the United States. Unfortunately they would be wrong. Hamilton was never the President of the United States, yet he had more of an impact on American history than many who were.
Alexander Hamilton overcame many struggles in his life. To list them all would more than consume the entirety of this essay. To provide a brief summary of where Hamilton began and ended his life, Hamilton went from poverty as an orphan living in the Caribbean to George Washington's right hand man during the Revolutionary War and later the first Treasury Secretary. Every step up involved overcoming enormous challenges.

Hearing first hand how he was able to solve these problems would be extremely interesting and would almost certainly provide valuable lessons. Perhaps every step of his life Alexander Hamilton challenged authority. To start, Hamilton was of illegitimate birth in an age where that actually mattered. His parentage is still debated by historians today. Every step upwards required challenging society's authority. Hamilton, in many ways, was born a rebel and constantly worked to challenge authority sometimes quite literally. In 1776 he served in the Continental Army as aide-de-camp to George Washington . In fact, many of the surviving field orders we have from George Washington directing troops on the battlefield fighting the British are in Hamilton's handwriting.
Alexander Hamilton managed to accomplish this all by being incredibly hard working and determined. To list a few instances of the fruits of is labor, he founded the Coast Guard, served as the lead defense attorney in America's first murder trial, served as a delegate from representing New York at the Constitutional Convention, then later wrote 51 of the 85 essays comprising the Federalist Papers defending the new United States Constitution in the span of 6 months, as Treasury Secretary, Hamilton created the First Bank of the United States (a precursor to the modern Federal Reserve), refinanced America's debt, and basically took the United States from bankruptcy to prosperity. Hamilton worked and wrote non-stop. Even though Hamilton died much earlier than most of the Founding Fathers we know more about him than any of them because of his prodigious writing.
Finally, Hamilton witnessed some of the most fascinating moments at the start of American history. He doubtless possesses innumerable tales on the other founders. His stories on working with George Washington as he did would no doubt provide hours of entertaining conversation, to say nothing of what he might say about his political rivals from his time. Another interesting period of time he might be able to shed some light on would be the Constitutional Convention itself. For being such an important event we have very little information on the event itself. All of these and more would be fascinating to learn about from a primary source as Hamilton.
Alexander Hamilton lived an incredibly fascinating life. He worked hard, he overcame many struggles, and he witnessed some of the defining moments of the beginning of the United States. He was also very handsome (so they say). These reasons and many more would make him a great addition for any dinner.