British commanders Howe and Gage debated their strategy for taking Boston. All agreed that Dorchester Heights was necessary for its security, including the Americans, but none would attempt to take it. The British dreamed of burning Boston—and the entire coastline—but they fortified Bunker Hill and dug in for the long winter instead.

But digging in was not as simple as it sounded. These British were not used to the American winter, and several men froze to death while standing watch.

The British officers fared much better. They tore down houses for firewood and turned the Old South Church into a place for horses and other kinds of entertainment. Another fine building was converted to a playhouse where they viewed Shakespeare, among other things. One night while the playhouse put on a farce about “General Washington” with his rusty sword as the “star,” loud booms were heard. The crowd laughed, thinking the boom was part of the show. It was not: The Americans were bombing Charleston, a waterfront neighborhood in Boston.

One important difference lay between the American military and the British. Colonists like Nathanael Greene moved through the ranks based on ability, while many of the English received their commissions through political relationships or cash.