- Sam is still aiming to buy back the bar, but is still a lot short on capital. Robin is getting death threats and thus is surrounded by a mass of security guards. The situations in Sam and Robin's lives intersect when Robin, who was planning on sailing his boat, aptly named The Rebecca, in the Cape Cod Regatta that afternoon, is called off on emergency business. Sam would love to sail the boat in Robin's place since the winner's purse is $10,000. Without Sam needing to ask Robin, Robin does let Sam sail The Rebecca in his place. Now, all Sam needs is a crew, so he enlists the help of Carla and ex-Coast Guard employee Norm. During the race, Sam is working his butt off, but Carla and Norm concede defeat when they drop into last place early on. All three change their minds as to their priority when Norm discovers a bomb on board the boat. They also discover the radio has been dismantled, the lifeboat no where in sight and although the life jackets are there, they can't jump overboard as the waters are shark infested. If they survive this ordeal, they each have their individual wants from Robin for placing them in danger.—Huggo
- Sam is still unsure just how he's going to raise enough money to buy back the bar. Salvation comes in the form of Robin Colcord, who is unable to sail his boat 'The Rebecca' in a Boston regatta.
When it's found out that the winner of the regatta will receive $10,000, Sam volunteers to sail Robin's boat for him.
Recruiting Norm and Carla as his crew, everything seems to be going well, until Norm finds a bomb in the mini-fridge aboard the boat. They attempt to abandon the boat, but find sharks swimming in the water, and the only life raft on board has been sabotaged.
Working together, they run the boat aground, and flee just before it blows up.
Returning to the bar, Robin talks with Sam about signing a damage waiver, but Sam claims he is upset that Robin seems more upset about his boat then the fact that Sam and his friends could have been killed. Robin apologizes, and is willing to write Sam a check for $60,000. Feeling that Robin is trying to buy his way into an apology, Sam refuses.
However, when he later tells Norm and Carla about the monetary offer, they 'abandon Sammy' and try to find Robin.
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