From Crown to Colonials.
It is difficult to pin down specific mistakes (i.e. tactical moments of failure) that have a direct and irrefutable bearing on war, as the number of variables that lead up to and take place after said mistakes are innumerable. I will, therefore, not discuss military tactics, but instead highlight three broader elements that, taken together, sum up Britain's biggest mistake during the war: consistent under-estimation of the gravity of the situation.
1.) Continental politics. It is well-known that France became involved in the American War of Independence out of a desire to challenge British hegemony in the wake of the disastrous Seven Years' War (also known as the French and Indian War in the US). What is less known is that Spain and Holland joined France in a coalition against Britain in order to weaken British power in the Caribbean and potentially extract Britain from Gibraltar. Meanwhile, Britain was also engaged (once again) in land warfare in India against both European and Indian armies. As such, it is more appropriate to view the American War of Independence as a continuation, and escalation, of hostilities started by the Seven Years' War. As a result of this coalition, and opportunism in India, British military resources were required on multiple fronts simultaneously, thus the colonial engagement included a fraction of Britain's actual military power.
2.) Military deployment. I don't want to get into specifics in terms of tactical thinking, however historians are in agreement over the fact that British command in the colonies overestimated the number of loyalists it could depend upon for supplies, manpower, and counter-revolutionary action. Furthermore, historians like Christopher Hibbert note that inter-officer rivalries and disputes over actions, authority, and hierarchy crippled logistical and tactical operations throughout the war. The former is a reflection of Britain's detachment from colonial culture and sentiment throughout the 18th century (a significant problem in the lead-up to the war), whereas the latter represents a long-standing problem with the British officer corps, one that would become the focus of a series of military reforms during the nineteenth century. In short, British command in the colonies did not cooperate on the level required to manage a rebellion, especially in a region of the world as rural and geographically difficult to navigate as the colonies were in the late-eighteenth century.
3.) Domestic support. Typically, the American War of Independence is viewed as a monolithic struggle between American 'patriots' and British 'imperialists.' The reality is far more nuanced. Support for the war in Britain was limited at first, and it became extremely unpopular over the course of the engagement. In fact, historian Stephen Conway asserts that the American War for Independence witnessed the first sustained and large-scale public criticism (at home in Britain) of the use of military force as an instrument of policy in western history. Whether or not this is true is up for debate, but the point remains that popular protests (and political fallout) surrounding the war were quite prevalent. In my opinion, this issue played the largest role in Britain's failure to retain the colonies. Popular and political distaste for the war at home soured British morale, led to stalled and/or delayed logistical and tactical support for operations in the colonies, and – ultimately – made the the concept of independence a potential reality long before it was clear that the war was lost.
Your latter question, 'could they have won it,' is hypothetical, and is thus impossible to answer with any certainty. Sure, they 'could' have won it, had battles gone their way and public opinion remained positive. The better question, I believe, is 'if they could have won it, would the outcome have been any different?' On this, I would argue that evidence points to 'no.' Popular opinion of the war, particularly with regards to the colonial right to independence, was extremely strong. Furthermore, influential economists (like Adam Smith) and politicians firmly believed that an independent America was of greater financial and strategic benefit to Britain in the long-term. On a side note, the fact that Britain had this revolutionary experience in the Americas, yet continued to escalate colonial obligations in Asia (and later Africa) is a topic that drives a significant amount of imperial historiography.
For more on this, see:
The British forces had a glaring opportunity to defeat the Continental army as soon as the main British army landed in New York in mid 1776.
New York was vital to the British as it was an ideal Naval base for the war effort. When the British landed in New York in July of 1776 British Army, under General William Howe numbered 32,000 whereas Washington in comparison had 20,000 men. In the Battle of Long Island the Americans suffered 2,000 casualties, 6 times their British counterparts. Arguably if Howe continued to press the Americans who were effectively trapped the war would've been over after the first major confrontation, however thankfully for Washington a dense fog enabled him to withdraw.
As well as the Howes been military commanders (William Howe's brother, Admiral Richard Howe was commander of the naval forces) they were also peace commissioners. Instead of utilising the momentum gained from the Battle of Long Island to destroy the Continental Army they now sought peace from a position of strength. On the 11th of September Admiral Howe met Franklin, John Adams and Edward Rutledge however this largely failed due to the Declaration of Independence and Howe not having the power to negotiate a treaty between the two parties. During this period Washington declared to Congress his strategic intentions which was to be a defensive war which avoided 'general action'. (I believe this policy was the principle reason Britain lost the war as it denied the British what they sought throughout the war from 1777, a decisive battle with the Continental Army.
The Americans suffered another major setback on the 16th of November when the British captured Fort Washington, taking nearly 3000 American prisoners in the process. This forced Washington into a full retreat. The prospects for the survival of the Continental Army were further diminished by many militiamen returning home. Once Washington reached Pennsylvania in December his army was around 3,000 men. To make matters even worse the one year enlistments of much of the army was soon over. It seemed Washington's Army and independence for the United States were about to disintegrate. On the 8th of December the British captured Newport, another crucial naval base for the British. On the 18th of December Washington wrote 'I think the game is pretty near up'.
Philadelphia, the US capital seemed to be ripe for the taking. However, Howe chose to quarter his troops throughout the winter. This meant Howe threw away an opportunity to further diminish American morale and perhaps ultimately destroy the rebellion.
Washington's army, down but not out was able to regroup and was reinforced by local militia. Washington wanted to end the military campaign on a positive note before quartering for winter. It was during this period which the Continental Army scored the famous victories of Trenton and Princeton. These victories meant the British gave up their gains in New Jersey and gave the American cause hope.
General Howe finally launched his campaign for Philadelphia in July 1777. (Although it effectively started in August due to questionable logistical decisions) On the 11th of September Howe again defeated Washington at Brandywine Creek, with the Americans sustaining 1200 casualties, twice that of the British. However again Howe missed an opportunity to destroy Washington's army. Howe went onto capture Philadelphia on the 26th. However congress fled to Lancaster which meant that the British would have to decisively defeat the main Continental Army, which they could have done previously with ease and now Washington's principle strategy was avoiding a potentially deceive major battle in which the Americans had no resource. Washington again withdrew and Howe again missed an opportunity to destroy Washington and quartered in Philadelphia for the Winter.
Throughout this period the British very much enjoyed an absolute position of strength but consistently ignored opportunities to destroy Washington's army which would have ended the war. It became apparent later on in the war that all the American forces needed to do to war was to survive - and the British allowed them to do this in 1776 and 1777. The British would never get opportunities afforded to them such as this throughout the rest of the war and the loss of Saratoga meant the British never enjoyed such a position of strength again and crucially was the impetus for French, Dutch and Spanish intervention which meant British resources were now divided between preventing an invasion of Britain as well as protecting possessions in West Indies, Africa and India.
As historians we don't deal in "What if?"s, so sorry to say I'm going to ignore the second part of your question.
The first part is rather easy, and essentially boils down to a string of strategic blunders made by the British leadership, particularly Generals Howe and Burgoyne early in the war.
In the fall of 1777 the British Army was in a great position; General Howe had garrisoned New York City, and Lt. General Burgoyne had secured Quebec. Their focus was on defeating the New England colonies, as they were seen as the primary agitators of the rebellion. The plan was, then, to take New York by pincer movement; Howe from the south, Burgoyne from the north, as other Royal elements held the west. The decision to be made was when they would execute this attack: they could either begin the campaign immediately, and hope to finish before winter, or garrison up and wait until winter passed. The decision was to begin immediately, as the rebels were weakened, and essentially surrounded. The plan was to crush them completely, and wrap up the war the next spring.
As Burgoyne began his march south through Canada, Howe made the decision to move his army out of New York City to take Philadelphia, then the seat of the Continental Congress. This put Burgoyne in a terrible position, who had decided to cut off logistical ties with his northern contingencies in the expectation of meeting with Howe's army. In addition to that, Burgoyne's Native contingents had abandoned him due to an earlier defeat.
Burgoyne's army fought with the rebel army in Saratoga over the course of about three weeks that fall. I'm not going to go into detail because the battle is obviously famous, and you can read that anywhere. However, it was Howe's change in strategy, and Burgoyne's neglect of his supply lines that left Burgoyne weakened and vulnerable, and ultimately resulted in his defeat, and his ostracism from the British military. This is typically considered the turning point in the war that allowed the rebels to gain the upper hand and continue on.
It should be noted that the war lasted an additional six years after the Battle of Saratoga, it was by no means decisive or easy for them. It did, however, allow for an easier winter for the rebel armies, gave them a strong foothold in New England, and allowed Washington to continue training troops for regular service to begin his offensive in the coming year. It also directly influenced France's decision to join the war, which arguably was all the rebels needed to shift the fight in their favor.
One of the most obvious blunders is General Burgoyne's decision to march across the New York wilderness from Quebec to the Hudson River. Attrition affected the British troops heavily and resulted in an important American victory at Saratoga. Saratoga is considered to be a pivot point that rose morale among the American patriots and helped convince France that the United States was worth supporting.
The greatest mistake for the British, however, was the campaign in the Carolinas. General Nathanael Green chose a strategy of attrition, evading major battles and forcing the British soldiers to live off the land. The South was more favorable toward the British, but the extended presence of the British Army eroded away that favorability.
But ultimately it was game over when France joined the war. The war of independence opened up into a global war. Britain could no longer focus its forces on a campaign or two. Instead, it had to devote forces to defending all of its colonies from France. It was at this point that Britain realized that it had bitten off more than it could chew and consider negotiations.
Really, it doesn't matter much how well the Continental Army performed. As long as France entered the war the revolutionaries would win. However, the Americans first had to prove themselves that they were worthwhile.
I haven't seen this addressed elsewhere - One of my college professors said that a big player in the outcome of the war was assistance from within Britain. Basically families having relatives here, and sending aid in one way or another. Is this substantiated? Did it play a major role?
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