English Military Failures Continue
Things went from bad to worse for the English. Robert Devereux, Earl of Essex, arrived as the new lord lieutenant in 1599 but proved spectacularly unsuited for the job. His military incompetence was exposed immediately.
At Curlew Pass, Essex sent Sir Conyers Clifford to rescue a besieged English ally. Clifford's 1,490 troops got trapped in unfamiliar terrain - mountains, woods, and bogs everywhere. Hugh O'Donnell's forces ambushed them, killing Clifford and a third of his army.
Essex's response? He basically gave up. Instead of fighting Tyrone as Elizabeth demanded, he secretly negotiated a truce and then fled back to England, disobeying direct orders. Elizabeth was absolutely fuming.
Reality Check: By 1599, Essex's army had shrunk from 17,200 to just 4,000 effective soldiers - disease, desertion, and defeat had destroyed English military power in Ireland.