The tea was on three privately owned merchant ships. One hundred and fourteen chests were on board the Dartmouth, the first ship to arrive in port. The other two ships, the Eleanor and the brig Beaver carried 228 chests between them, along with other cargo. As the ships sailed into Boston Harbor, they each passed by Castle William to the south, which was under the command of a British officer and had upwards of a hundred cannon. When the ships came into the harbor, but before they docked, port officials boarded them. That meant that they had officially reached port and that their movements were now under the command of port officials instead of their captains.

Behind the tea-laden ships, British Admiral John Montagu brought a squadron of warships to prevent the colonists from forcing the ships back out to sea before they were unloaded. This put the captains (and the ships' owners) in a bind. If the tea wasn't unloaded, customs weren't paid. And if the ships tried to sail back out of port, Montagu would stop them and charge them with failing to pay customs on their cargo that was due, according to him, because they had already entered port.

After a few days, the colonists had the ships come in close to Griffin's Wharf. The Sons of Liberty organized a continuous watch of the vessels. Twenty-five men on each shift ensured that the ships were not unloaded under the cover of darkness, or at least to sound an alarm if there was an attempt. The ships' captains came ashore and left the mates on board. The situation remained the same for more than two weeks.

Thomas Hutchinson, the royal governor of colonial Massachusetts, clearly understood that the colonists were angry, but he did not anticipate that they would damage the cargo. He was counting on the fact that after 20 days without having paid customs, the customs authorities—with the assistance of British sailors and soldiers—could legally impound the tea from the ships, and then, from Castle William, disburse it in small amounts to a few merchants who could resell it. This would circumvent the colonists' effort to make sure that the tea did not enter Massachusetts. Hutchinson and the apprehensive merchants who were willing to receive the tea had holed up with the troops in Castle William.

Boston was not under martial law, so soldiers were not policing the city, although Hutchinson could have brought a detachment of soldiers in, had he known beforehand the particulars of a threat. He did not post a military guard at the wharf, however, perhaps to avoid provoking a confrontation with the crowds keeping watch there.

On December 14th, when the 20 days of waiting were almost up, Hutchinson wrote his brother Elisha about the excited Bostonians, "I hardly think they will attempt sending the tea back, but am more sure it will not go many leagues: it seems probable they will wait to hear from the southward, and much may depend on what is done there." (Hutchinson, 96) Yet Hutchinson also believed the colonists might take some form of direct action if an attempt was made to land the tea onto the wharf.

Just after six o'clock on the night of December 16, 1773, a group of about 60 men daubed their faces with burnt cork, coal dust, or donned other makeshift disguises, armed themselves with hatchets, and formed a raiding party. Some of them styled themselves "Indians."

They made their way to the wharf. The Sons of Liberty's watch was already there, and still others joined them, either to assist or simply to see what was happening. The raiding party formed three groups of 50 each, and boarded all of the nearly deserted ships at about the same time. They met no resistance.

Lendall Pitts, the commander of the group that boarded the brig Beaver, "sent a man to the mate, who was on board, in his cabin, with a message, politely requesting the use of a few lights, and the brig's keys—so that as little damage as possible might be done to the vessel;—and such was the case. The mate acted the part of a gentleman altogether. He handed over the keys without hesitation, and without saying a single word, and sent his cabin-boy for a bunch of candles, to be immediately put in use." (Thatcher, 181–2).

The moon shone brightly too, so their work was well lit. The night was very quiet and neither the crowd on the wharf nor the raiding party spoke much. Onlookers at the wharf, as well as the men on some of the closer British ships, however, quite distinctly heard the sounds of the chests being staved in.

The party quickly brought the 342 chests of tea (a total of 90,000 lbs.) onto the deck. They split them open and threw the tea and the chests overboard into the harbor. The party took care that no other property on board the ships was harmed, and that none of the raiders took away any of the tea. They even swept the decks clean of loose tea when they were done. They worked quickly, apprehensive of a possible attack from Admiral Montagu's squadron, part of which was only a quarter of a mile away.

Montagu watched the affair from the fleet, but he took no action because of the cargo ships' position next to the wharf. "I could easily have prevented the Execution of this Plan," he wrote the following day in a report, "but must have endangered the Lives of many innocent People by firing upon the Town." (Labardee, 145) Instead, he rowed ashore and watched from a building nearby, even briefly exchanging taunts with the Indians.

The tea party lasted three hours, finishing around nine o'clock. The raiding party then formed in rank and file by the wharf, and, shouldering their hatchets, marched, accompanied by a fifer, back into town, dispersed, and went home.

The next morning a large, winding mound of loose tea still floated in the harbor, and a party of colonists rowed out in boats and sank it down into the waters with their oars. The British fleet witnessed this, too, but did not interfere.

The disguised men's identities were kept secret by their fellow Bostonians, and Governor Hutchinson was unable to charge the members of the raiding party, but Parliament responded five months later (news traveled back and forth across the ocean very slowly then) with a series of measures meant to force Boston to heel.

After British victory in the Seven Years War (1756-1763), Parliament attempted to better organize the British Empire. Among other things, Parliament, led by the ministry of George Grenville, enacted the Sugar Act of 1764 and the Stamp Act of 1765, and so for the first time taxed the British North American colonies. The Sugar Act amended the Molasses Act of 1733 by lowering the duty on French West Indian molasses from 6d per gallon to 3d. Reducing the duty made purchase affordable and so encouraged what the higher duty had discouraged.

The colonists denounced the Sugar Act. They reasoned that British subjects had a sacrosanct right to have their property protected. The power to tax threatened property unless the taxing body was chosen by the tax payers and also had to pay the same taxes it required others to pay. The British House of Commons met neither requirement when it taxed the colonies, and so the colonists concluded that taxation without representation violated property rights.

The colonists made the same argument in response to the Stamp Act. But the Sugar Act was enforced primarily on the oceans and by the navy, meaning that the colonists could not physically prevent the tax from being assessed. The stamp tax required that to be legal most paper products—newspapers, court documents, marriage licenses, wills, even playing cards and dice—carry an official stamp. To work the tax depended on colonists within colonial communities selling the stamps, making suspected stamp distributors vulnerable to the pressure of their neighbors. The Grenville ministry announced the stamp tax in February 1765 to go into effect in November. In the intervening months the colonists protested, rioted, and intimidated anyone suspected of taking the office of stamp distributor. Led by the Sons of Liberty, the colonists made the Stamp Act unenforceable before it even began. In 1766 the new Rockingham ministry repealed the Stamp Act but only amended the Sugar Act lowering the duty to 1d per gallon. The experience showed that the colonists opposed all parliamentary taxation but that they could much more easily prevent internal taxes than external ones.

The Chatham ministry came to power in 1767 and enacted new taxes, the Townshend Acts, that year. These external taxes taxed lead, glass, paint, and especially tea. The Townshend Acts provoked the same ideological criticism and led colonists to have grave concerns that British liberty was not safe within the empire. Because the taxes were external they were much harder to prevent but by 1769 the colonists had organized a boycott movement. Growing tensions caused troops stationed on the western frontier to be reassigned to Boston, which led to the famous Boston Massacre on March 5, 1770. The new first minister, Lord North, had already decided to repeal most of the Townshend Acts, which were threatening to tear apart the empire.

In 1770 North repealed all of the acts except for the tax on tea, the most lucrative of the taxes. The remaining tax kept relations tense and suspicious. Finally in 1773 North sought to resolve the impasse. He replaced the last Townshend Act with the Tea Act of 1773. The act was meant to bail out the East India Company, make clear Parliament’s authority to tax the colonies, and make the price of tea cheaper for colonists than it had been before. North reasoned that no colonists could fear an act that made them drink cheaper tea. He was wrong and the Boston Sons of Liberty threw 342 chests of tea into Boston Harbor on December 16, 1773. The Boston Tea Party destroyed tea worth £11,000 or about $1.5 million today. That was the last tax Parliament ever imposed in the colonies. The Tea Party caused the passage of the Coercive Acts of 1774, which were punitive laws meant to punish Massachusetts, but were not taxes. The Coercive Acts led to the first and second Continental Congresses and, ultimately, to the declaration of independence. So taxes did not cause the American Revolution, but taxation without representation did create a climate of suspicion and fear that provoked the events which did.

It is fascinating to consider what might have happened had the American patriots lost their war against Great Britain. Certainly British victory in the conflict was entirely plausible. Indeed, given the significant disparities in resources between the British and the colonists, such an outcome seemed not just possible but likely early on, and at numerous points during the conflict. The Patriots lacked a professional army, a central government, and a navy; the 13 colonies were geographically dispersed and lacked Britain’s political unity. The Patriots waged their war for independence against the world’s premier military and its most powerful empire, only a decade and a half removed from its great triumph over France in the Seven Years’ War.

It is impossible to know with certainty what would have happened if the colonies had lost the War of Independence. Historians refer to such “what if?” as counterfactuals—because they occur in an imagined world where a different sequence of events took place, there is by definition no factual evidence on which to base historical analysis. Without documentary sources to work with, answers to these questions are speculative by nature. Nevertheless, it is possible to make some educated guesses about the nature and probability of different outcomes.

Certainly the timing of the Patriot defeat would have had an important effect on the events that followed. The War of Independence was a protracted struggle (it remained America’s longest war until the Vietnam War in the 1960s), and throughout the conflict the British alternated between coercive policies and conciliatory policies. At moments, the British seemed intent on punishing the rebelling Patriots so harshly that they lost the will to continue their military struggle; at other moments, the British pursued far more generous policies intended to pacify the colonists and persuade them to willingly give up their struggle for independence. (Several historians have suggested that the vacillation between the two policies itself undermined the royal cause. When pursuing a policy of coercion, they appeared cruel; when pursuing policies of conciliation, they appeared weak. Refusing to commit fully to either strategy since it made the British seem indecisive and weak-willed.) Some historians have argued that the consistent application of either of these policies might well have resulted in British victory in the war’s first few years. Instead, their alternation between carrot and stick dragged out the war and contributed to the colonists’ growing resolution.

Whether the Patriots surrendered during a period of British conciliation or during a period of more punitive British policy would have had significant impact on the terms of the peace that followed. Had the British prevailed during one of the periods in which Parliament took a more severe approach to prosecuting the war, it is not difficult to imagine fairly harsh treatment for many of the rebellious colonists. Certainly some of the most influential instigators and leaders of the independence movement would have received unforgiving treatment from their conquerors: in the eyes of Parliament, of course, the Patriot cause was not an independence movement but blatant treason against the crown.

Surrender during one of these punitive phases would have had some serious consequences for the defeated. At least some key figures in the rebellion would have been tried and imprisoned if not executed outright. Larger numbers of Patriot supporters would likely have been stripped of their land or possessions; some may have been forced to flee. Here the real-life experience of British loyalists in the colonies following the British defeat at Yorktown is instructive. British surrender forced many of those families to forfeit their land and businesses; finding the newly-independent colonies an extremely unwelcoming place for those who had supported the losing side, many fled to British-controlled Canada to avoid further persecution.

Had the British defeated the colonists during a more conciliatory phase, it seems likely that their treatment of most of the Patriots would have been substantially more generous. Many of Parliament’s attempts to persuade the rebelling colonists back into the empire rather than force them militarily were, after all, predicated upon fairly liberal terms: in many cases, Patriots who surrendered their arms and took oaths of loyalty to the crown would be spared the most harsh punishments. Because failure to abide by those promises could have been politically disastrous for the British, it is plausible to imagine much more forgiving terms at particular junctures in the war.

Speculating as to the long-term results of a British victory in the War of Independence is necessarily even more vague. It is somewhat difficult to imagine the British ruling the expanding colonies indefinitely; as Thomas Paine wrote in Common Sense, the notion of a relatively tiny island ruling a land so great in both territory and population in perpetuity was a difficult one to reconcile. Here again the real-life experience in North America may provide some useful insight: it is not difficult to imagine that, like Canada, the colonies might ultimately have broken away, gradually and peacefully, to become an independent political entity several generations later.

Given that it took enormous determination, military aid from the French, and more than a little luck for the colonists to defeat the British in the War of Independence, it is perfectly reasonable to speculate as to what might have happened if the colonists’ military fortunes had stumbled. By definition, counterfactual questions can never be answered with precision; in this case, the combination of historical guesswork and real-life examples can lead us to a number of plausible outcomes depending on the nature of the Patriots’ defeat.