Seasoned horse jockey Jackson (Clifton Collins Jr.) has weathered decades of races on the riding circuit, but he now finds himself facing what could be his last season as his health deteriorates. With the help of Ruth (Molly Parker) and a promising new horse, Jackson starts to prepare for the upcoming championship. His plans take a left turn when a budding young jockey (Moisés Arias) shows up and claims to be his son. Caught between yearning for a connection and uncertainty about his own future, Jackson confronts difficult questions regarding his legacy.
Billionaire, software mogul, Adam Pi has everything in life with the exception of positive memories from High School. He begrudging goes to the 20th reunion and has such an amazing time he finds himself wondering If I knew then what I know now and offers the entire grad class one year's salary to come back and do one more month of the 12th grade.