Plot

Shawn and Gus arrive at the scene of a plane crash in time to find that the pilot wants the duo to avenge his death - and the two proceed to investigate the man's pretentiously wealthy family.

Begin with a flashback of Young Henry explaining to Young Shawn that all families are weird in some way.

Shawn and Gus join the SDPD as it searches for hedge fund wizard/billionaire Warren Clayton. Using one of Henry's maps the guys locate Warren's downed plane. Clayton mutters several unclear phrases including the word Waterloo and asks them to find out who killed him before dying. Shawn takes the responsibility of finding Warren's killer very seriously.

Clayton's widow, Alice, is impressed with Shawn's knowledge of her husband and hires the guys to find his killer. She tells him Waterloo is the name of the 18th hole of their country club's golf course. Shawn tells her he needs to "become" Warren in order to investigate his murder.

Abigail tells Shawn she would like to meet Henry and help repair the relationship.

At the Clayton estate, Alice tells Shawn and Gus she had begun taking tennis lessons. Alice tells them her daughter Nyna is "no longer with us." Clayton's son Garvin is skeptical of Shawn's abilities. Shawn outs Alice for having an affair with her tennis instructor, and housekeeper Rosa for being Clayton's mistress. Shawn announces he will prove one of them murdered Clayton and the guys are quickly fired.

Lassie tells Shawn that Clayton's crash has been ruled an accident. The plane simply descended too rapidly. Shawn is able to convince Karen they should still look into foul play.

At the country club the guys speak with several members who knew Clayton. Clayton was one of the few hedge fund managers to show a profit in the rough economy. One of the members, Chad Wiswall, admits he lost Clayton's airplane to him in a golf bet and tells them Clayton had begun spending more time with his family, even building a private hangar. Shawn believes a family member sabotaged the plane. He calls Abigail and finds her at Henry's place. They are planning a dinner for the three of them.

At the hangar Shawn discovers that Clayton made a four-hour stop in Bakersfield which was not recorded on the official log.

During the stop, a car service took Clayton to an environmental watchdog organization run by a Mrs. Thomas. Thomas admits they talked business for a few hours and that Clayton had been at odds with the organization since her and her husband Charles started it. Clayton was looking for her endorsement in a business move Thomas "didn't approve of." The guys leave the meeting convinced Thomas was one of Clayton's mistresses and she may have killed him because he was trying to reconcile with Alice.

After learning that a change in his will meant the bulk of Clayton's estate was being left to Thomas' non-profit, Shawn and the SBPD arrive at the will reading convinced she is the murderer. When she arrives, however, they discover Thomas is in fact Nyna Clayton Thomas, Clayton's daughter. The guys are quickly fired again.

At the station Nyna tells Shawn she didn't want anything to do with Clayton or his money because he had been such a lousy father. She also overheard him talking with Wiswall about problems with his investments.

Wiswall tells the guys Clayton's fund was actually a Ponzi scheme. Wiswall called Clayton before he died to try and get his plane back but Clayton wasn't interested. Wiswall said he kept all of his investment records and was planning to out Clayton to the SEC.

Shawn has dinner with Henry and Abigail. Shawn is disappointed with Henry's lack of communication. Gus sends Shawn a text that Wiswall is going to turn over his Ponzi evidence and they need to meet Lassie and Jules.

The guys arrive at Wiswall's hotel to find he has been murdered. On the floor Shawn spots the investment record folder and realizes he saw matching records shredded in the recycling bin at Nyna's non-profit.

Shawn interrupts Clayton's funeral to tell everyone it was Charles who killed both Clayton and Wiswall. When Charles realized Clayton was going to change his will to take money from their non-profit he rigged the altimeter on Clayton's airplane. Since Wiswall blowing the whistle on Clayton would freeze his assets, Charles killed Wiswall as well.

Shawn and Henry apologize to each other but still don't come to a full understanding.