Fourteen-year-old Benny Neusner wants only one thing more than a dog: for his neglectful mother to be proud of him. He hasn't given up on impressing his mother, but a dog is out of the question. His father and stepmother will never permit it. They don't understand how lonely he is. He is not a brain like the other kids in his therapeutic school, and nothing he's tried has ever worked out for him. Benny meets Bess Rutledge, a 70-year-old woman who has dreamed of winning the Westminster Dog Show all her life. Despite her decades-long career as America's top Standard Poodle breeder, she has never entered Westminster, and now she thinks she's too old. She sells off all the dogs in her once famous kennel except for the aging champion McCreery and Breaker, McCreery's handsome, mischievous son. She offers to give Breaker to Benny, but Benny wants a real dog, not a sissy poodle.

Benny is drawn into the world of dog shows and becomes convinced he has found the perfect way to gain his mother's attention. If he can win Westminster with either McCreery or Breaker, he is sure she will be proud of him at last. But first he needs to convince the reluctant Bess to come out of retirement, Benny wins Bess over when she recognizes a connection between Benny's relationship with his mother and her own indifferent mothering when her grown son was Benny's age. Benny shows unexpected talent in the show ring as the two unlikely friends, Benny and Bess, race against time to build up Breaker's credentials as a champion. They overcome a variety of challenges in the show ring and at home while teaching each other important lessons about families and forgiveness. Now the only questions left to decide are who will go into the ring at Westminster: McCreery or Breaker? Benny or Bess? In an ending full of surprises, dreams come true in unexpected ways where winning can be losing and losing is almost perfect.