The episode opens with Milton and another first grader playing marbles in the playground when a group of bullies led by Chucko Kowalski start picking on them and hold them down whilst they steal all the marbles. Vince turns up and confronts them telling them to stop or he'll stop them just like he's done plenty times before.
The rest of the Recess Gang celebrate Vince's win as something really cool but he brushes it off as nothing. T.J. tells Vince to face it, that there is nobody cooler than him but Vince replies what about his big brother Chad. The group start discussing Chad who Vince calls the Coolest guy Third Street School has ever known. Mikey talks about how he remembers that when he was all in kindergarten all alone in the sandbox Chad came over to play with him. Spinelli remembers that back in first grade when she got a bean stuck up her nose, it was Chad who showed her how to get it out. The group agree that Chad is cool but say that they haven't seen him in years. Vince says that Chad just so happens to be picking him up from school today.
The kids of the school hear that Chad is visiting and get excited as it seems that Chad helped them all out as well. The Diggers says that it was Chad who give them there first shovel and got them interested in digging. The Ashley's hear and say that they remember him from first grade as a hunk. King Bob remembers Chad from when he was a mere fourth grader when Chad actually spoke to him and give him aspirations of being king some day.
After school all the kids are still in the playground waiting for Chad and are disappointed that Chad is nothing but a nerd. The next day the group tell Vince that Chad is a geek but he doesn't believe them still thinking of his brother as cool. The gang point out various geeky thing Chad has or does such as wearing a pocket protector, wearing tape on his glasses, and being the score keeper for his schools base ball team. Vince thinks about what the group were saying later and walks into the house, seeing Chad's trophies and team picture from "future Geeks of America" club and realizes that the group were right.
Vince confronts him and finds out that Chad knows he's a geek and is OK with it. The next day at school the Recess gang try to reassure Vince that it's OK Chad is a geek but Vince says everything that he ever believed to be true is wrong and fears that he too may turn into a geek. The gang says that that isn't going to happen but Vince still think it is and says nothing can get any worse. This is when Chucko Kowalski's brother turns up and confronts Vince about him giving his little brother a "hard time". His brother pushes Vince to the floor and is about to beat him up when Chad turns up and tells him to stop and threatens to stop helping him with his math homework if he doesn't.
Chucko Kowalski's brother, afraid he'll fail math without Chad's help, apologizes and walks away. The kids celebrate and Vince tells his brother that what he did was cool, with Chad replying that just because he's a geek doesn't mean he's not a cool geek. The two walk off to Chad's bike and ride off.
- Chad, Chucko, Cheay, Buster, Jocko, and Vince's parents debut in this episode.
- This is the only time where Chucko is a major bully. Beginning in the next season, he becomes part of Lawson's gang and a background character with no speaking lines.
- This is the first time a sibling of a member of the main gang is introduced.
- Chad strongly resembles Steve Urkel from Family Matters.
- This is the first episode where Upside-Down Girl has a speaking role.
- At the end of this episode (And "King Gus", which it was paired up with), the 1985 "Rainbow Disney Castle" logo for Walt Disney Television introduces a variant where the background is dark purple instead of indigo.
- This was the first episode written by Jon Greenberg.
- This the fourth appearance of King Bob.
- T.J. Detweiler/Chucko Kowalski - Ross Malinger
- Vince LaSalle - Ricky D'Shon Collins
- Ashley Spinelli/Kindergartener - Pamela Segall-Adlon
- Gretchen Grundler - Ashley Johnson
- Mikey Blumberg - Jason Davis
- Gus Griswald - Courtland Mead
- Dave - Ryan O'Donohue
- Sam/Kid #1 - Klee Bragger
- Upisde-Down Girl/Ashley Boulet - Francesca Smith
- King Bob - Toran Caudell
- Ashley Armbruster - Anndi McAfee
- Ashley Quinlan - Rachel Crane
- Chad LaSalle/Cheay - Kenny Blank
- Cy Kowalski - Justin Shenkarow