Raymond III, Count of Tripoli

Raymond inherited Tripoli at twelve after Assassins killed his father in 1152, spending his youth at the royal court in Jerusalem. Captured in 1164 fighting Nur ad-Din, he spent nearly a decade in an Aleppo prison before ransoming himself into debt and marrying into Galilee's wealth. He served twice as regent - first for the leper-king Baldwin IV, then for Baldwin's nephew Baldwin V - but court rivals kept blocking him, culminating in Sibylla and Guy of Lusignan seizing the throne in 1186 while Raymond sulked in Nablus. Furious, he cut a deal with Saladin, letting Muslim forces cross his territory. Reconciled only when invasion loomed in 1187, he led the vanguard at Hattin and watched the Christian army destroyed in the desert heat, exactly as he'd warned. He escaped to Tripoli and died weeks later, probably of pleurisy, leaving historians split: brilliant strategist or self-interested lord who let Jerusalem fall.