In Capricorn Chuck's World of Pain, we delve deeper into the life of Chuck and his family as they face a formidable force hell-bent on swindling them out of their inherited land. The stakes are high as the nefarious attorney involved is held captive, awaiting a potential murder trial in the very prison where Chuck and his old companions once worked. As the plot thickens, new dubious characters emerge, adding more layers to this gripping saga.

Chuck, who penned a successful book in the predecessor, is now tasked by his publisher to create another masterpiece for a TV show. Amidst the chaos, he and his sister embark on an ambitious project to transform their father's land, Gussy's Pitts, into an expansive horse ranch, complete with cottages for nature enthusiasts. However, their brother Gary is less than thrilled about the venture.

Enter the Cowboy, a swift and efficient executor for his enigmatic boss, surrounded by henchmen like the intimidating Butch Gro and the explosive-loving ex-Captain Gill Sellek from the 911 war. Chuck's personal life is equally tumultuous. He separates from his wife Kelly Ann, continuing his affair with her step-sister Samantha Dixon, who bears an uncanny resemblance to his deceased love, Shandi. This resemblance stirs up old memories and causes friction between Chuck and Samantha.

Meanwhile, a charming land developer arrives in Wolford city, taking over the casino and hotel project. His intentions remain unclear. Chuck's best friend, Jed Ferrari, steps into the role of the new Attorney General after the previous one's murder. The new Senator for Massachusetts, Chip Karrington, persistently tries to persuade Chuck's family to allow the city of Wolford to use their land, Gussy's Pitts, as an access route to smaller towns. Amidst all this, Chuck's brother returns home for a grand wedding.

The first book concluded with a cliffhanger, revealing a potential mastermind behind the chaos - Thorn. In Capricorn Chuck's World of Pain, the mystery unravels further, promising a thrilling ride.