While many patriots during Revolutionary America are oft remembered for their triumphs on the battlefield, orations in the courtroom or diplomatic missions abroad, John Hancock is best known for the simple yet stylish swoop of his pen. On this day in Boston history, we celebrate John Hancock’s 277th birthday and take a look back in time as to why his name became synonymous with signatures, examine his contributions to the Revolution and Commonwealth of Massachusetts and question his legacy as an immoral smuggler.

Hancock’s role in the formation of the United States was as crucial as that of George Washington, Thomas Jefferson or John Adams. Though perhaps not quite as skilled in battle or diplomacy, his leadership and local presence were huge in fostering patriotic morale. Having presided over the second Continental Congress, it was his iconic signature that inked the document first. But you already knew that. So to help ring in Hancock’s 277th here are some fun facts you may not have known about this Beacon Hill boy.

1. He was wasn’t always rich

Though Hancock is known for being one of the wealthiest men of the colonial era, he didn’t always live such an affluent life. He was born and raised to a modest family in Braintree (now Quincy). His reverend father and mother owned one slave and lived comfortably, but it wasn’t until his father passed away and he was sent to live with his uncle Thomas that Hancock came into the big bills. Thomas Hancock was a successful merchant, importing British manufactured goods and dispatching rum, whale oil and other New England delicacies. When Thomas passed away with no sons of his own, his business went to John.

2. He had loyalist sympathies

As his uncle was so successful and cultivated relationships with similar British merchants as well as prominent government officials, so too did John. With connections overseas and with colonial authorities, Hancock was initially opposed to independence. Hancock gained favor, though, with locals and joined the cause when the Stamp Act – a tax on nearly all paper goods – was imposed. He then joined in a British boycott refusing to trade for their goods.

3. Sam Adams was his mentor

Sons of Liberty stalwart, vocal supporter of separation from Britain and namesake of one of Boston’s favorite adult beverages, Samuel Adams was an early mentor to Hancock during the latter’s rise through local political ranks. Though the two made an unlikely pair – Hancock with his opulence and taste for luxury, and Adams with a more Puritanical outlook on life – they made an effective team, getting Hancock elected to the Massachusetts House of Representatives in May of 1766 and pursuing a Whig agenda.

4. He wasn’t really a smuggler

John Hancock didn’t really smuggle goods into Boston Harbor. This label was slapped upon him as a means of British propaganda when enforcing the Townshend Acts – a series of restrictive legislation that imposed unfair taxes and trading regulations in an attempt to strengthen the British stranglehold over its empire. Americans were only allowed to trade with British entities, but in order to enforce this, they went after the wealthiest merchant in the colonies, meaning Hancock. When British customs officers unlawfully boarded and seized his mercantile ship Liberty, a mob ensued as to the wrongfulness of their actions. They claimed his shipment was small in size and therefore the tax was subsequently small, and also that Hancock unloaded much of his cargo in the middle of the night to avoid the duties. A trial ensued causing more unrest in Boston and he was eventually cleared of all charges, but his reputation as a smuggler stuck.

5. He wanted George Washington’s job

Perpetual patriot John Adams was arguably the most distinguished statesman of the time, but one of his most celebrated actions was nominating George Washington as Commander in Chief of the continental army. But Hancock, always thirsty for fame and glory, was hoping he’d be suggested for the job. According to an account by Adams, Hancock was “mortified” that his name wasn’t submitted but, after heading the second Continental Congress, he trekked back to Boston to become the first and third Governor of Massachusetts.