Back to the present day. Sort of. Our story wraps up as an older (but not particularly wiser) Jack returns to Mackinac Island and reconnects with old friends. ... but one last surprise awaits.

Jack's forced to risk it all with one last load. After a summer of expected twists and turns, the dockporter is forced to put his money where his mouth is and see if he really has what it takes to conquer his demons, both real and imagined.

The gang takes a nighttime journey off the island to St. Ignace, Michigan for a caper, some shenanigans, a sprinkling of antics, and the requisite questionable judgment calls. But the cause is noble, and it's summer. Decide for yourself if it was worth it.

Jack's world seems to have crumbled, but he gets one last chance to make things right when a mysterious load of luggage arrives on the docks. Is Blackjack still a possibility? Listen and find out!

Jack gets inspired by an unlikely ally and embarks on a mission to end all missions. The risks are high, and the stakes even higher. But with good friends and a complete lack of fear, the dockporters rally.

Jack gets some bad news, but he handles it very well. Not really. Truthfully, the name of the title should give you a general idea of what happens. It's a small island, but he manages to cause big problems.

Jack and Erin get to know each other, share family secrets, and experience the foot-pounding joy of a Mackinac Island pub going full-throttle. But alas that foot is wearing a shoe and that shoe? It's about to drop.

Jack moves out of one life and straight into another as his world on the island goes pear-shaped. Luckily, he's got Erin and there's no possible way he could screw that one up. Right?

A chapter in life when everything changes in the snap of a frayed bungee cord. Jack may have gotten himself in over his head with his bet, but things are about to take a tragic turn, and our hero will have to dig deep. Thus, the title of the chapter.

Jack and Smitty pay a little visit to Swanksville. They strap on jackets and ties and head up to the Grand Hotel dining room to spy on Erin as she eats lobster and berates her boyfriend in her own unique Irish style. Jack falls harder and Smitty is unimpressed with the price of a beer.

Jack leaps for Erin, and things don't go as planned. In a word, his misadventure can be described as "aquatic." It'll all make sense when you listen.

Jack decides to start learning about weight ratios and aerodynamics if he's going to ride 21 suitcases, aka "Blackjack." Along the way, he takes an unfortunate detour past the Grand Hotel. While his skills are questionable, the end result is a chance meeting with Erin, the cello player at the fancy hotel. In romance novels, they call it the Meet Cute. But in this case, there's horse manure involved, which negates that idea.

Jack makes a fateful bet with his frenemy Gordon to ride 21 bags in the basket of his bike before the summer is over -- or pay the ultimate price. Meanwhile, actor slash dockporter AJ catches the eye of a beautiful starlet on the island to escape terrible reviews of her latest movie. Yes, things are heating up in the summer of 1989.

Summer of 1989. Jack is 21 and has become what he always wanted to be: a dockporter. We meet his motley gang of luggage hounds as they hustle for tips, discuss the day's important issues (mainly bungee cords) and deliver the luggage to the island's hotels. But a dark cloud arrives in the form of Jack's old friend Gordon, now a smooth-talking developer. His big idea? Replace dockporters with golf carts.

We whip back to 1976 and meet a young Jack McGuinn on Mackinac Island. He's got his eyes on his future, even as a kid. Someday he will haul luggage like the dockporters he admires weaving through the busy streets of Mackinac. But for now, he's content to scam fudge and hustle signed Gordie Howe hockey pucks for his Gramps.

Chapter One finds our hero, Jack McGuinn, stuck in a rut in Los Angeles, a working fashion photographer and hating it. He receives a letter from an old friend about a wedding on Mackinac Island and dumps it all, and hits the road. On the ferry ride to the island, he's persuaded to spin a yarn that takes him back in time.