British General William Howe had a coveted opportunity to destroy the Patriots once and for all. In 1776, Howe sieged Washington’s troops in New York, leaving them with little more than an option to surrender or fight to death. Yet Howe let the Patriots escape. Washington recounts this episode to his elder brother Samuel:
We found that General Howe had no Inclination to make an Attack upon our Lines at the last mentioned place—We discovered at the sametime by their movements, and our Intelligence, that with the assistance of their Ships they intended to draw a Line round us, and cut of all communication, between the City and Country; thereby reducing us to the necessity of fighting our way out under every disadvantage—surrendering at discretion—or Starving—That they might have accomplished one or the other of these, if we had stayed at New York, is certain…
In hindsight, this was a terrible decision by Howe. The Patriots wouldn’t hold the high ground till later—in fact, the plan to seize the Hudson River in 1777 would have been devastating to the Continental Army had it not been scrapped. Yet Howe again decided to focus on another place, Philadelphia, paving the road for little gain and, if anything, a big loss for his fellow General John Burgoyne at Saratoga.
Despite being a brilliant general, why did Howe make these decisions that ultimately strengthened the Patriots and allowed them to extend a war to seven years of conventional and non-conventional warfare, eventually convincing Howe to resign and Great Britain to withdraw?
I'll provide my usual caveat that I'm not the most qualified person to answer this, but I hate seeing questions go unanswered. You've hit on one of the most perplexing aspects of Howe's career, one that historians have debated ever since: His inability (or lack of desire) to land a decisive blow to Continental Army.
A minor few things to clarify- firstly: Washington’s army wasn’t really besieged in New York- in fact Washington had early realized that defending New York from a seaborne invasion would be extremely difficult, so he tried to defend the spots he thought he could and definitely felt that, politically speaking, he could not abandon New York without a serious fight. Washington was basically surrounded after his defeat at the Battle of Brooklyn, but managed to escape (the first of his near-miraculous escapes from British forces).
The second is that while Howe’s plans to attack Philadelphia in 1777 would seem to be totally contrary to Burgoyne’s plans to take control of the Champlain-Hudson corridor (and ended up being so), but both of those plans were approved by Lord George Germain back in London. Germain ultimately needs to take a large portion of the blame for approving two mutually exclusive plans.
As why Howe let Washington’s army escape from Long Island after the Battle Brooklyn- I think it can be attributed to a few reasons: Firstly, the British had marched a long way around to the flank of the Continental defenses on the Gowanus Heights, and were tired, the second is that Washington had the Continental forces that remained there dig in.
This gets to one of the more salient points about Howe: He had witnessed (and participated in) the Battle of Breed’s Hill, and how incredibly dearly dearly that British victory was bought, in terms of casualties. The Battle of Breed’s Hill accounts for some 25% of British officer casualties for the ENTIRE WAR- It had hardly been better for the enlisted men. Howe had seen first hand how well even ill-disciplined Continental forces had fought from behind hastily constructed entrenchments. Indeed, Washington deliberately tried to get the British to recreate the Battle of Breed’s Hill several times during the war. Howe was not eager to allow that to happen again, so he would always decline Washinton’s invitation to attack him when Washington was entrenched (as he would later in 1777 at the Battle of Brandywine, and again at the Battle of White Marsh).
Another factor that’s harder to quantify, because Howe didn’t speak much about it, is the fact that Howe had always been sympathetic to the Whig party in England, and the cause of the Continentals. This might have grown some from the fact that his elder brother’s tomb in Westminster tomb had been paid for by the Massachusetts's assembly (Viscount Howe had been wildly popular with his American provincial forces in the Seven Years War). Howe had publicly opposed the Intolerable Acts before the war, and stated that “My going thither was not of my seeking. I was ordered and could not refuse…” Indeed, many people at the time accused William Howe, and his brother Admiral Howe, of being unwilling to end the war. A great cartoon held by the Library of Congress on that here:
https://www.loc.gov/item/2004673330/
People have debated ever since to what degree William Howe’s personal sympathy affected his command on the battlefield, and there isn’t a general consensus on that matter. When Howe resigned his command, he returned to England and published his own account of his actions. You can read that here:
https://archive.org/details/cihm_42874/page/n13/mode/2up
To get an idea of the types of criticism that was written about him at the time, I’d suggest reading Joseph Galloway’s pamphlet Reply to the observations of Lieut. Gen. Sir William Howe on a pamphlet entitled "Letters to a nobleman"... which is conveniently online:
https://archive.org/details/cihm_20597
For some insight into the decision making by Germain in London, I’d suggest reading the first part of Richard Ketchum’s Saratoga: Turning Point of America's Revolutionary War.
Works cited:
Galloway, Joseph. A reply to the observations of Lieut. Gen. Sir William Howe on a pamphlet entitled "Letters to a nobleman" : in which his misrepresentations are detected and those letters are supported by a variety of new matter and argument; to which is added an appendix containing… London: 1780.<https://archive.org/details/cihm_20597>
Howe, William. The narrative of Lieut. Gen. Sir William Howe in a committee of the House of Commons, on the 29th of April, 1779, relative to his conduct during his late command of the King's troops in North America. London: 1780.<https://archive.org/details/cihm_42874/page/n13/mode/2up>
Ketchum, Richard. Saratoga: Turning Point of America's Revolutionary War. New York: Henry Holt and Company, 1997.
Edited: Spelling.
Edited: More spelling - sorry folks.