Complex sentence: Manteo enters the historical record through his encounter with English explorers in 1584, when Sir Walter Raleigh despatched the first of a number of expeditions to Roanoke island to explore and eventually settle the New World.
Split into simpler sentences: Manteo enters the historical record through his encounter with English explorers in Roanoke in 1584. In 1584 Sir Walter Raleigh had despatched the first of a number of expeditions to Roanoke island to explore and eventually settle the New World.