Win Win (2011)

New Providence, New Jersey lawyer Mike Flaherty, who has his own small firm, suffers from anxiety due to financial problems. Those problems stem from insufficient work for the firm, increasing overhead with the building in which he operates literally falling apart before his eyes, and increasing costs at home in taking care of his family. Being a lawyer, he refuses to supplement his income by doing work he thinks beneath him, although he does a side job with his law firm assistant and friend Stephen Vigman coaching the less than adept wrestling team at his alma mater, New Providence High School. He is shielding everyone around him from these financial problems, including that family consisting of his "bark worse than bite" wife Jackie, and their two preschool aged daughters, Abby and Stella, although his long time best friend, Terry Delfino, who is facing his own issues in hatred fixation of his ex-wife and her new partner living in "his" house, does find out Mike's problems out of circumstance. To solve his financial problems, Mike seizes upon a less than ethical opportunity concerning a court appointed client, Leo Poplar. Wealthy Leo is at the early stages of dementia, but would rather live "at home" as opposed to the probable court order to send him to a care facility. The whereabouts of Leo's only known family, his daughter Cindy, with who he has been estranged for twenty years, is unknown, she the only real candidate to act as Leo's guardian if he were to continue to live in his house. When he learns that Leo's guardianship includes a $1,500 per month stipend, Mike convinces the court to allow him to assume guardianship of Leo. Mike, in turn, places Leo in that care facility while he collects that $1,500 per month basically doing nothing on Leo's behalf, he telling those that ask only one half of the story, either that he is taking care of Leo, or that the court ordered Leo to move into the care facility. Complications ensue in the case when Leo's teenaged grandson, Kyle Timmons, who Leo didn't even know existed, unexpectedly lands on his doorstep wanting to live with him. Based on Leo's situation but knowing nothing about about Kyle beyond the guilt by association of what Leo had mentioned about deadbeat Cindy, Mike, with Jackie's reluctant approval, decides they have no other option but to take Kyle in until they locate Cindy to take him back. Although one issue that Mike learns about Kyle's past buoys that notion of keeping him around longer than anticipated, Mike knows Cindy's eventual arrival and what he eventually learns about her relationship with Kyle can only make what he's doing with Leo more tenuous.