Chuck's new purchase of a boat creates a rift between Dan and his longtime friend. Meanwhile, Darlene hires her first assistant at Wellman’s Plastics but soon realizes she is anything but helpful, leading Darlene to question her decision. Elsewhere, Jackie is laser-focused on her dream of being a contestant on "JEOPARDY!" and believes the late, great Alex Trebek wants her to go all the way.
Jackie is studying for game shows. Darlene can not handle the demands of Becky nor can she find a good secretary. Mary has fun on Chuckie's boat, as well as rivaling with Josh & Harris. Chuckie and Dan compete about who is the most jealous. Later, he tells Dan about boat loads of news.
Jackie is watching an episode of Jeopardy!, shouting a response. Dan wants to know what she is talking about. He also says it is a tragedy that Jeopardy! lost another host. However, she said that Alex Trebek talked to her in a Vision Quest. Dan has to say no to Mary's request to go have fun doing things such as Laser Tag. Immediately after that, Chuckie drops by to invite Dan and Louise to a party. He has a new truck and a new boat that he got to reward his family. Mary immediately goes to spend time with Chuckie. This, along with Dan's longer resume, infuriates him. Chuckie does not understand why Dan is so infuriated. He blames Dan for oppressive jealousy and leaves even after Dan calms down.
Darlene gets her first very large office. Robin says the job can include an assistant if needed. Robin insists that Darlene gets an assistant. Becky demands Darlene repair the rigged time clocks. Becky gives her very important advice about who to hire. Darlene ignores the very important advice, and hires a girl that resembles Alice Johnson, Karen Valentine, from Room 222. Despite Lisa's very friendly, even overwhelming personality, she is very sneaky.
Dan asks Jackie why she is weighing the kitchen table with all those spontaneous text books. Dwight walks in to tell Dan that Chuckie demands reimbursement for construction equipment and other supplies. Dan believes it is be cause of the fight with Chuckie's boat. Dwight confirms that Chuckie is leaving the business and asks for a promotion. Before he leaves, Dan tells Dwight to let Chuckie know he is going to have to wait for his money.
Lisa tells Darlene that she answered a telephone call on her behalf. Jeanette From Sales is very angry. Lisa says it is necessary be cause Jeanette might be intimidating Darlene. Darlene leaves to straighten it out.
Josh, Harris, and Mary are fighting over the living room television. Harris says it is past Mary's bedtime and changes the channel to C-SPAN. Mary tells Josh about the family's mental illnesses. Harris is forced to clarify that it is a severe drug and alcohol addiction. Mary brings up Josh's immense wealth. As they leave, Mary grabs the remote.
Jackie sees Mary but lets her watch television. She goes to see Dan in the kitchen. He is still upset about Chuckie. He jokes about letting the equipment and tools see Chuckie every other week. Jackie tells Dan to go to him. She also quite humourously says that Dan does not have a choice. She is in the middle of going through all the times Chuckie was there for them until she receives a message. She is able to go to an audition. Jackie intends to buy a boat if they like her, as well as start a rivalry between The Conner Family and The Mitchell Family.
Now Becky and Darlene are in the kitchen. Lisa intercepted Becky's demands to repair the time clock. Lisa, posing as Darlene, told Becky to tell every body that they are forbidden from even making eye contact with Darlene. Darlene says that it is a good idea, but did not like Lisa using her account. Becky says that Darlene should have listened before hiring Lisa. She says that Lisa must be fired, but Darlene wants to give Lisa another chance. Darlene hates all the time she got fired, but Becky says she can do it instead since she was not fired as often as Darlene. Darlene says she is going to have to clean her own mess by mentoring Lisa.
Dan sees Chuckie and his boat, which is named Anne Marie II. They get in to further conflict when it turns out that The Mitchell Family are very good with finances. Despite being paid much less than The Conner Family even during their worst jobs, they surpassed them quickly and easily. Dan says that it is very embarrassing. Dan tries to cheer him self up, until he finds out even more: Despite The Conner Family's two restaurants, The Mitchell Family are better cooks! They talk about the argument they had during their Coffee. He says that he brought the boat to thank Dan, not brag, nor take Mary. He explains that it is necessary for Dan giving them a chance. He says Dan that Native African Blacks find difficulty finding jobs, even finding customers. In either situation, the result is the same. Caucasians routinely get paid much more at jobs, and are automatically trusted by their customers. He goes on to say that Caucasians have more banks. When Dan asks why Chuckie why he did not say any thing all these decades of friendship, Chuckie says ... It is very embarrassing. Dan probably understands, but wants Chuck to come back to work with him. Chuckie says that he wants to retire from full time construction, leaving Dan behind to work for ever, yet struggle. However, they are still welcome to go with them on their boat. Chuckie says that the boat will always be stocked with beer. Dan says he wants to convert his furniture to hold bear as well.
Darlene gets to be a mentor earlier than expected. Lisa stopped by to let Darlene know that she tried to reassign Darlene's parking spot to the accessible area. Darlene warns Lisa that she is over stepping her authority, but thinks she can be mentored. However, it turns that Lisa has much more experience than Darlene. She is not struggling at all in the slightest, and lied on the application so she can swindle her. Darlene fired Lisa, but Darlene says that a consolation she says that Lisa has a screw loose.
Darlene decides to ban Lisa from Wellman and says to Lisa's replacement to look out for her. However, Darlene's new assistant is even worse. Darlene's new secretary is a bounty hunter that offers to go after Lisa. She also says that Darlene is possessed, but Lisa can be saved by blood atonement. She says for $250.00 U.S.D., she can put a Hex on Lisa. Darlene nervously wraps up the interview.
- John Goodman as Dan Conner
- Laurie Metcalf as Jackie Harris
- Sara Gilbert as Darlene Conner
- Lecy Goranson as Becky Conner
- Michael Fishman as D.J. Conner (credit only)
- Emma Kenney as Harris Healy
- Ames McNamara as Mark Healy II (credit only)
- Jayden Rey as Mary Conner
- Jay R. Ferguson as Ben (credit only)
- Alexandra Billings as Robin Shetsky
- Stephen Monroe Taylor as Dwight
- Milo Manheim as Josh
- Emily Pendergast as Assistant Lisa
- Betsy Baker
- Despite being credited, Michael Fishman (D.J.), Ames McNamara (Mark) and Jay R. Ferguson (Ben) do not appear.
- It is revealed in this episode by Jackie, that Chuck was the first person Dan contacted when Roseanne died.
- Two of the Jeopardy! hosts: Alex Trebek, and university professor Art Fleming, have died of pancreatic cancer.
- One of Alex Trebek's other game shows: To Tell The Truth, copied the set design and music of Jeopardy! twice. First it copied "The All New Jeopardy!". Later, it picked up the glowing large block letters that Jeopardy! used, but the theme music was orchestral. Jeopardy! made changes to its set and music at that time.
- After The Conners episode aired, a five time champion Blayden Smith died also.
- It is revealed that Chuckie has grandchildren.