Donald “Sully” Sullivan (Paul Newman), a sprightly yet weary 60-year-old hustler and con-man, navigates life in the tranquil, frosty village of North Bath, New York. Making a living as a construction freelancer, he often finds himself teamed up with his not-so-bright friend, Rub Squeers. Trouble brews with the local contractor, Carl Roebuck, as Sully consistently sues him for unpaid wages and disabilities, much to Carl’s annoyance. Sully’s inept lawyer, Wirf Wirfley, fails to win any of these cases, and their interactions often lead to unintended comedy.

In an amusing twist, Sully pushes Carl’s buttons by openly flirting with Carl’s wife, Toby, who seems to enjoy the attention. A regular at the Iron Horse Saloon, Sully shares drinks and card games with Wirf, Carl, Rub, and the town sheriff, adding to his colorful social life.

A recurring gag through the film involves the theft of Carl’s snowblower. Sully snags it to get back at Carl after yet another legal defeat, only for Carl to reclaim it, locking it up under the watchful eye of his doberman. Sully comically outsmarts the dog and steals it back again, leading to a cat-and-mouse scenario that keeps the audience chuckling. The final theft sees Carl leaving the perturbed dog at Sully’s childhood home as a pointed message.

Sully lives with the elderly Miss Beryl Peoples, who faces pressure from her banker son, Clive Peoples Jr., to evict him. Complications arise when his estranged son, Peter, an out-of-work college professor, comes to visit, bringing an opportunity for reconciliation. While navigating this relationship, Sully begins bonding with his young grandson, Will. Peter’s frequent presence creates tension with Rub, but Sully reassures him that while Peter is his son, Rub remains his closest friend.

Amidst these personal dramas, Clive’s plans for an amusement park deal in North Bath collapse when his partner turns out to be a con artist. Overwhelmed by shame for misusing the bank’s resources, Clive discreetly exits town.

Sully’s luck takes a turn for the worse after a confrontation with Officer Raymer lands him in jail. However, Peter comes to his rescue, and both he and Sully’s grandson start to form a bond with him. Attending the funeral of a local elderly lady named Ms. Hattie, who he used to help, reflects Sully’s caring nature amidst his often cheeky antics.

Then, fortune smiles upon Sully when he hits it big with a horse racing trifecta ticket, winning thousands. Toby reveals her interest in leaving Carl behind and embarking on a spontaneous trip with Sully to Hawaii, but he realizes he cannot abandon Will. Grateful for her affection, he turns down her offer just as she prepares to leave for the airport.

In the film’s closing moments, Sully finds himself back at Miss Beryl’s, yet he embodies a new sense of contentment. Richer both in finances and personal growth, he’s also embraced a new canine companion, signaling that despite the twists and turns, life can indeed bring unexpected joy.