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The Pretty Lady was a boat originally stolen by Reed Carter in order to start his charter business. However, after Jake Hanson and Amanda Woodward invested their money into his business, Reed soon used to the boat to smuggle illegal drugs. When Jo Reynolds stumbled upon the supply in the cargo hold, Reed attacked her and locked her inside, mentally torturing her for days.
Eventually, Jo got loose and ended up killing Reed in self-defense. She was picked up by the coast guard and taken into custody, but was found innocent of murder.
Later, Jake took over the charter business, but used the boat as a personal place for solitude as well. After picking up Brittany Maddocks one night in the ocean, she stayed there and seduced him long enough to plant explosives on the boat. However, she was soon revealed to be working with Palmer Woodward, who was out for revenge against Jake for turning him into the F.B.I. for illegal dealings.
After Jake, Palmer, and Brittany went out into the ocean, Palmer had planned on killing Jake, but his plan backfired when Brittany turned on him, shooting him. Brittany offered Jake the chance to come with her with Palmer's money, but he declined and she left him on the boat to die. However, the boat exploded and Jake was able to jump into the ocean before being caught in the blast. Jake got an insurance settlement as part of the incident.