Gumball, Darwin and Anais discover that Mr. Wilson has been picking on Richard for most of his life; ever since he humiliated Richard with a high school prank. The kids try to work Dad through it but when their efforts fail, they realize that getting back at Mr. Wilson is the only way to break the cycle.
The episode begins with Richard about to park in front of the Elmore Mall with Gumball, Darwin, and Anais in the backseat, but Harold rear-ends their car. He then walks up to Richard's car window and throws his keys at Richard, telling him to park it in the shade, then proceeds to discuss his birthday party before informing Richard that he wasn't invited. Harold laughs and walks off.
While clothes shopping, Harold reappears, jokingly replacing Richard's pants with a much tighter pair. Later, when grocery shopping, Harold calls Richard through the intercom telling him to "come collect his dignity from the front desk." Richard tries to dismiss it as friendly teasing, but the kids are not convinced, especially after Harold proceeds to give Richard a painful wedgie, pulling the underwear over his shoulders. Gumball suggests that Richard should tell Nicole about it, but he thinks that would only disappoint her.
Anais proposes that Richard gets some legal advice on the situation. However, their lawyer proves to be too expensive, stopping mid-sentence to ensure that Richard continually pays for her service. Eventually he runs out, forcing Anais to use a Daisy Dollar, causing the conversation to briefly continue in the form of a song. They all decide that it's not worth the effort, and as the lawyer approaches the door to escort them out of her office, she freezes again. Darwin takes advantage of the opportunity to steal candy from a bowl on her desk.
Richard and the kids sit sadly outside, but Darwin offers Richard a piece of the candy to cheer him up. Right when Richard is about to eat it, though, Harold drops by on a one-wheel hoverboard and steals the candy. Gumball angrily concludes that if Richard can't beat Harold, he has to get on his level, but Anais interjects, claiming that Richard does not have it in him to act badly. Offended, Richard attempts to roast the kids, but inadvertently showers them with compliments. He tearfully apologizes for what he said afterwards, with Anais concluding that he requires professional help.
They go to a psychologist, where Richard explains where the humiliation first began. In a flashback to high school, Richard receives a letter from Principal Brown, stating that he was to be named prom king. After Granny Jojo helps him build up confidence and contours his face, he goes to the prom and happily jumps on-stage as Principal Brown is about to announce who was named prom king. However, before Richard can give a speech, Principal Brown clarifies that it was not Richard who won and that the 'letter' he received was fake. Richard asks who would do such a thing before seeing Harold begin to chuckle, causing the whole room to erupt in laughter.
Back at the psychologist's office, Richard begins to discuss the stress problems that his bullying caused (dandruff, acid reflux, balding, and gas). Before he can continue on, though, the kids interrupt him and point out that Harold was the psychologist all along, pulling off a fake mustache to reveal his identity. Shocked, Richard's stress problems are all unleashed at the same time, causing everyone else in the room to react in disgust.
Eventually, the kids decide to play dirty to enact revenge, forging a signed blank check with (after some confusion) a value of $1,000,000,001. They jump behind the fence as Harold approaches. Upon seeing the check, he excitedly hires Yellow Guy as his butler and tells him to throw dollar bills on the floor as he walks. Deciding the bills not decadent enough, he instead decides to walk on gold coins and eventually diamonds on a red carpet, causing him to wince in painful ecstasy with each step.
Richard and the kids failed to stop Harold, having been knocked unconcious jumping over the fence and falling into a canal. When they come to and get back across the fence, the kids are satisfied with the prospect of Harold ruining his life by spending money he did not have, but Richard is not, seeking to act like an adult and tell Harold the truth.
The scene then cuts back to Harold as he quits his job while roughhousing and kissing his former employer, buys a gold-plated car (before making his exit via gold-plated helicopter), and replaces his wife with Jazelle, escorting her out of the house as he prepares to detonate it and replace it with a 70-foot-tall statue of himself. Yellow Guy carries a diamond-crusted plunger detonator, but Richard stops him right pefore he pushes down.
Richard starts to clarify the issue with the check, but Harold interrupts him by pointing out some skywriting mocking Richard. He nervously laughs before whispering something to Harold who, in understanding, takes back what he had thought about Richard and assures him he would not make the same mistake again.
On the walk home, Anais asks what Richard said to Harold, which turns out to be advice on maximizing the effect of the dynamite in detonating the house. An explosion then goes off in the background, ending the episode.
This is Harold's second major role in the series. His first was in "The Bus."
Richard's teenage design is the same one from "The Choices."
One of the pictures on the lockers in Richard's flashback is the propaganda poster from "The Vision," featuring Hector.
Richard mocks Anais for warning him not to lick an electrical outlet, like he nearly did in the episode "The Flakers", and for reminding him not to forget his appointment at the cardiologist, like how he mocked Nicole for reminding him in the episode "The Limit."
When Anais inserts her specialized Daisy the Donkey dollar bill into the lawyer's box, the music that plays sounds similar to that of "The Candy Mountain Cave" song from the Youtube series, Charlie the Unicorn.
The Daisy dollar that is used for Daisyland is a direct reference to the Disney dollars used as currency for the Disney parks and Disney stores.
Harold's behavior towards Richard seems to contradict previous, more passive reactions between the two characters, with the two even working together as equals in "The Bus."
However, it can be assumed that they simply had a common goal in that particular episode.
The poster featuring Hector shouldn't appear in Richard's flashback as it takes place long before "The Vision" and was imagined by Gumball and Darwin in the first place.
When the spotlight is on Richard, Mr. Corneille can be seen in the corner without pixellation. When it shows Harold laughing, though, Mr. Corneille is back to normal.