Charlie, Alan and Jake Harper first have met Teddy in the episode Prostitutes and Gelato, when he and Evelyn walk in on them in the Malibu coffee shop. Trying to avoid their mother, all three hide in the Men’s room, where Teddy plays with them for a while, and later reveals that their mother wants to see them.
After Evelyn introduces them to each other, they depart. The same night, he offers Alan and Charlie to come with him to Las Vegas in his private plane through a Limo to watch a fight with ring side seats, while staying in a pent-house suite.
Though Charlie initially declines, Teddy convinces him to come along. At Las Vegas, Teddy asks Evelyn’s hand in marriage from the brothers. Alan immediately accepts, while Charlie remains stubborn. However, Teddy wins both their hearts by getting them prostitutes.
The next day, Evelyn breaks to them that she broke up with Teddy. Both brothers persuade her to take him back, and she gives in when her current lover, Hugo, dies of Viagra overdose.
Teddy later appears to be settled down with Evelyn in her home. Near this time, Alan has a fight with Charlie, and stays with Evelyn for a few days. Desperate to get some alone time together, Teddy and Evelyn try to resolve Charlie and Alan’s issues, eventually being successful.
Later, Teddy and Evelyn announce their marriage, and he introduces his daughter Courtney Leopold to Alan and Charlie. Charlie immediately falls for Courtney, but stays away from her on Teddy’s request. Courtney, however keeps coming closer to him, and after sleeping with him, blackmails him into buying a Ferrari from her, or she would announce their one-night stand to Teddy and Evelyn. Charlie eventually gives in, and buys the Ferrari.
As the wedding approaches, Teddy announces in front of all family members that he doesn’t require a pre-nuptial agreement with Evelyn, claiming ‘What’s mine is yours’. Courtney over reacts on this, and upon Charlie’s asking tells him that she has lost her job, about to lose her condo, and desperately needs $ 50,000. Charlie gives the money to her, and both start a relationship. Moments before becoming her step-brother, Charlie proposes marriage to her.
Hours after the marriage, Teddy is found dead in Charlie’s bed with a boner and his pants slid down, implying that he was having sex with someone else before his death. The CSI team investigates the case, and find out that Teddy is actually Nathan Krunk, a con artist. Courtney is actually Sylvia Fishman, his partner in crime and lover. It was revealed that he died while having sex with her due to a heart attack, and that he used bad checks and stolen credit cards to pomp and show. The main reason for marriage to Evelyn and without a pre-nup was to get her money.