Win Win 2011

In the quaint town of New Providence, New Jersey, attorney Mike Flaherty (Paul Giamatti) juggles the demands of his legal practice and his passion for coaching wrestling. Balancing his duties becomes increasingly difficult as he strives to keep his family – including his wife Jackie (Amy Ryan) and their two young daughters, Abby and Stella – shielded from the dire financial issues he faces.

The plot thickens when Mike is appointed guardian for Leo Poplar (Burt Young), a court client suffering from early dementia, who has no known relatives. In a calculated move, Mike convinces the judge for a monthly stipend of $1500. However, the situation takes an unexpected turn when Leo’s troubled grandson Kyle (Alex Shaffer) arrives from Ohio, seeking refuge with his grandfather. With Leo relocated to a senior care facility, Mike and Jackie decide to welcome Kyle into their home.

As the story unfolds, they learn of Kyle’s challenging family dynamic, including a mother in rehab with a boyfriend. After joining wrestling practice, Kyle’s remarkable talent shines through, leading Mike to enroll him in his high school, where he hopes to turn the struggling wrestling team into formidable contenders.

Their harmonious arrangement is soon threatened by the reappearance of Kyle’s mother, Cindy (Melanie Lynskey), recently out of rehab and intent on reclaiming custody of both her father and son, along with their substantial inheritance. The tension escalates when Kyle discovers that Mike had initially promised to keep Leo at home but subsequently moved him to a nursing facility. Feeling betrayed, Kyle brands Mike as a money-hungry opportunist like his mother.

Faced with the consequences of his actions, Mike has a revelation and strives to rectify the situation for both Leo and Kyle. In an act of genuine care, he proposes to Cindy that she leave her son and father in his custody in exchange for his monthly payment. This change of heart leads to Mike and Jackie permanently welcoming Kyle into their family and returning Leo to his home. To manage their financial issues, Mike decides to take up bartending, prioritizing the well-being of his new family and friends.