In this episode, Tracy brings in a youth baseball team (from the worst neighborhood in New York) he's coaching for community service. Jack is very excited about this – baseball taught him how to win and dream. The kids don't have many dreams – their role models are R. Kelly and Michael Vick. Later, Jack comes to Tracy's practice and brings the kids new uniforms.
In the writer's room, Jamie, the coffee guy, delivers their coffee. Jenna tries to hit on him and Frank falls in love with him. While Liz is working in her office, Jamie asks her out for Saturday night. Jamie says he's 25 and thinks Liz is 29. Liz lets him believe she's 29 and agrees to go out with him.
Liz looks for an outfit in wardrobe while Jenna tells Liz what they are – cougars. Cougars – hot older ladies that pounce on their young prey. Frank walks in dressed in a tight tank top. He's figuring some stuff out about his sexuality.
Tracy and Jack meet before the practice. Jack is trying to figure out which biography of Winston Churchill to give to the team to inspire them. Tracy tries to tell Jack that Knuckle Beach is a different world - here orange soda is an acceptable substitute for breast milk there. Jack says he doesn't need to understand their world to help them – just like what Bush is doing all over the globe. At the game, the team loses and Jack decides to take over. He fires Tracy and puts Kenneth in charge.
On their date, Liz and Jamie reveal their real ages – 37 and 20. Liz runs into Jack who asks if they met at an amber alert. Jack encourages Liz to have fun and keep going out with Jamie. She sees Jamie struggling to get a drink from the bartender and rushes to help him. Jack receives a call from Kenneth about the status of the team. Kenneth reports that conditions are deteriorating but Jack says that removing Tracy was bound to cause unrest but they must stay the course.
At practice, the boys are fighting with each other and won't listen to Kenneth. Kenneth tells Jack that the team was better under Tracy. Jack says that Tracy didn't know what needed to be done and he had to go. The kids destroy all the things Jack bought for them. The kids chase Kenneth and Jack with the bats.
At the studio, Liz runs into Jenna who is with Aidan – a freshman at NYU. He plays games, drinks a lot of soda and wears shoes with wheels.
Jamie comes in with the coffee and asks Liz out to lunch. She says she's swamped but gives him a video game when he is disappointed.
Jack comes in to talk to Tracy and makes Kenneth apologize for him. Kenneth says that his arrogance created chaos and things are out of control. Jack says there are two options: cut and run and betray the people or create a coalition. The kids wrote Tracy letters to come back. With Tracy's know-how and Jack's resources, Jack believes they can turn the kids into winners. Jack's plan is one word: surge.
At the game, the kids are winning because of the addition of a few experienced Dominican batters.
That night, Liz comes to pick up Jamie and meets his mother – who looks just like Liz. She decides to shut it down.
Jack and Liz walk through the halls and discuss her experience with Jamie. He says Jamie was good for her – opened her up to new experiences, new points of view and stimulating conversations. He says there a few exceptions. They see Aidan repeating everything Jenna says and fighting like kids.