Win Win

In the quaint town of New Providence, New Jersey, Mike Flaherty struggles to balance his busy legal practice with his passion for coaching wrestling. This balance becomes increasingly precarious as he navigates the financial difficulties that threaten his family's stability.

Mike is appointed guardian for Leo Poplar, a court client suffering from early dementia with no known relatives. He cleverly secures a monthly stipend of $1500, intending to manage both Leo's and his family's needs.

The dynamics shift when Kyle, Leo's troubled grandson, arrives from Ohio seeking refuge. Concerned about his grandfather, Kyle unexpectedly becomes part of Mike's household, complicating their family situation.

Mike and Jackie learn about Kyle's challenging family background, which includes a mother struggling with addiction. This new information highlights the difficulties Kyle has faced, adding to the complexity of their living arrangement.

After joining wrestling practice, Kyle's exceptional talent is quickly recognized. This discovery inspires Mike to enroll Kyle in high school, hoping to elevate the struggling wrestling team with his skills.

Just when things seem to settle, Kyle's mother, Cindy, reenters the picture. Recently out of rehab, she intends to reclaim custody of her father and son, seeking to gain access to their inheritance.

The tension escalates when Kyle discovers that Mike had initially promised to keep Leo at home but later moved him to a nursing facility. This revelation causes Kyle to feel betrayed, accusing Mike of being similar to his opportunistic mother.

Confronted by Kyle's anger and his own actions' consequences, Mike has a moment of clarity. He realizes the importance of rectifying the situation for both Leo and Kyle, motivated by a desire to protect them.

In a bid to secure Leo and Kyle’s well-being, Mike proposes to Cindy that she allow him to take care of both in exchange for his monthly stipend. This offer reflects Mike's newfound determination to prioritize their needs over his own.

Following the agreement, Mike and Jackie welcome Kyle permanently into their family. This new arrangement creates a supportive environment where Kyle can thrive and build a relationship with Leo.

As part of the resolution, Mike takes the necessary steps to bring Leo back home. This decision highlights Mike's commitment to keeping families together, showcasing the importance of love and understanding.

Despite the positive changes, Mike faces ongoing financial challenges. To manage the family's expenses, he decides to take a bartending job, showcasing his willingness to do whatever it takes for his new family.

With Kyle on the wrestling team, Mike's coaching strategy begins to bear fruit. The hard work pays off as the wrestling team starts to show significant improvement, building a strong bond among teammates.

As they adapt to their new roles, the Flaherty family grows closer, embracing the challenges and successes together. The experience teaches them the value of unity, resilience, and unconditional love.