50 Pence - Elizabeth II The Jolly Roger

The Jolly Roger's connection to the Isle of Man is less decorative whimsy than genuine history — the island's position in the Irish Sea made it a provisioning and fencing point for pirates operating along Atlantic trade routes during the early 18th century. Whether any of the most notorious captains who flew the skull-and-crossbones made direct use of Manx harbors is debated, but the island's legendarily loose customs enforcement of that period made it a known weak point in British revenue control until the Revestment Act of 1765 forcibly brought Manx trade law under Crown authority.