On 9 May 1787, when Simon Starr left his family plantation in northern Virginia and started his five-day horseback ride to the constitutional Convention in Philadelphia, he carried with him the letter of instruction his father had sent from his deathbed in western Massachusetts: “…make plans to fill my spot…Fashion a strong new form of government but protect Virginia’s interests.”  More than most delegates, Simon appreciated how difficult it would be to fulfill these two commands.

                In the first place, his elders in Virginia had made it clear that he and the other delegates were authorized merely “to correct and improve our present Articles of Confederation, and under no circumstances to meddle with any new form of government.”  For him to achieve what his father had wanted, a strong central government would require ignoring these instructions.

                In the second place, he realized that a new union could not be established unless the three big states – Massachusetts in the North, with its manufacturing; Pennsylvania in the middle, with it commerce; Virginia in the South, with its tobacco and cotton plantations – found some way to protect their majority interests while ensuring the small states like Rhode Island, New Hampshire and Delaware a respectable voice in whatever form of government emerged.  Up to now, it had been one state – one voice, but with the big states constantly accumulating more power and responsibility, such an imbalance could not continue.  Rhode Island did not carry the weight of Virginia in population, trade or wealth, and to claim that she did was folly.

                He was perplexed as to how this impasse would be resolved, but he was sure of one thing; he would never allow Virginia’s rights to be trampled.

                Simon was twenty-eight years old that spring, a graduate of the College of New Jersey at Princeton, red-headed, quick to anger, interested in all aspects of American life.  He had served as foot soldier in the latter years of the Revolution, rising to the rank of captain, but he had known none of the commanding figures of that period.  In recent years, however, he had corresponded with two of the most brilliant men in Virginia or the nation, George Mason and George Wythe, the dazzling professor of law at William and Mary College.  Simon was literate, informed, patriotic, and determined to conduct himself with distinction at the Convention.

                As he left that May he assured his wife and young son:  “I’ll be back for the fall harvest,” and as he rode down the long lane to the highway, he called out the same message to the slaves who lined the pathway to bid him farewell.

                In his compact canvas saddle bags he carried four books he had come to treasure at college:  Thucydides’ account of the Greek wars, John Locke’s treatise on government, a book by Adam Smith on the political economy of nations, a saucy novel by Henry Fielding.  In his head he carried about as good an education as was then available in either the United States or Great Britain, but in both Princeton and Virginia he had been careful to mask any pretension to superiority.  He was an earnest young man of solid ability who would always show deference to his elders.  As one of the two youngest members of the Convention he would feel himself at a disadvantage, but he intended to associate himself with older men of talent and make his contribution through supporting them.

                He rode into Philadelphia, a burgeoning city of some forth thousand, in the late afternoon of Sunday, 13 May 1787, and without difficulty he found Market Street, the main east-west thoroughfare, which he pursued toward the Delaware River until he came to Fourth Street.  Here, in accordance with instructions, he turned south till he saw ahead, swaying in the evening breeze, the reassuring signboard of the Indian Queen Tavern.  He tied his horse, took down his saddle bags, and strode inside to announce himself to the innkeeper:  “Simon Starr of Virginia, for the room assigned to my father, Jared Starr.”

                At the mention of this name, several men who had been idly talking showed great interest and moved forward to meet the newcomer.  In the next exciting moments he met members of the Virginia delegation, including four men of distinction:  Edmund Randolph, James Madison, and the two older scholars with whom he’d been in correspondence, George Mason and George Wythe.  Looking carefully at each as he was introduced, he said:  “And General Washington’s a Virginian, too.  Add him to you gentlemen, and Virginia’s to be strongly represented,” and Madison said quietly: “We planned it that way.”

                One night during the waiting period Starr returned to the Indian Queen, to see a group of delegates speaking with a newcomer, a slender, handsome, self-0contained young man of thirty, so compelling in his manner that Simon whispered to a friend:  “Who’s that?”  and when the man said:  “Alexander Hamilton, just in from New York,” Starr gasped so loudly that the newcomer turned, gazed at him with penetrating eyes, and said, almost grandly:  “Yes?”

                “I’m Jared Starr’s son.”

                And now the icy reserve which Hamilton had been showing melted in the sun of remembered friendship.  Elbowing his way out of the crowd, he hurried to Simon, embraced him warmly with both arms and cried:  “When I learned of your father’s death I felt mortally stricken.  A man rarely finds such a trusted friend.”

                They spent three hours together that first night, with Hamilton probing in a dozen different directions to determine Starr’s attitudes, and as the evening waned, it became clear that the two men had even more in common than Hamilton had had with old Jared Starr.  Both believed in a strong kind of central government, in the right of large states to exercise large powers, and particularly in the sanctity of property.  But toward the end of that first exploration Simon heard several of Hamilton’s opinions which could be interpreted as an inclination toward a monarchical form of government:  “Simon, the world is divided into those with power and those without.  Control of government must rest with the former, because they have most at hazard.  Whatever kind of supreme ruler we devise, he should serve for life and so should the members of the stronger house, if we have more than one.  That way we avoid the domination of the better class by the poorer.”