Nathaniel Plimpton III is a Stanford educated lawyer and new co-owner of Whitefeather & Associates. He is from a prominent Los Angeles family who run the law firm of Plimpton, Plimpton & Plimpton. He and his family were looking to extend their business into the San Gabriel Valley and bought the West Covina firm as part of that expansion. Nathaniel's brusque, elitist and no-nonsense personality has made him very unpopular with his staff, particularly Rebecca Bunch. His first appearance was in the Season Two episode "When Do I Get to Spend Time With Josh?". He is portrayed by actor Scott Michael Foster.
In the fall of 2016, on Nathaniel Plimpton III's first day as the new co-owner of Whitefeather & Associates he called a staff meeting in the boardroom. The firm's star attorney Rebecca Bunch arrive late which he chastised her for and insisted she make her job the main priority in her life. Rebecca quit immediately uninterested in a high pressure job but Nathaniel was unfazed since without her on payroll he could fire fewer employees. Rebecca took back her resignation and assured Nathaniel she could bring in revenue to avoid lay offs. He gave her until the end of the week and later had lunch with Darryl at Home Base who advised he tone down his management style. Nathaniel then revealed he was now the sole boss as he had bought additional shares of the firm from Darryl's ex-wife.
Nathaniel returned to the firm where he stayed late to come up with a list of employees to fire. Rebecca was also there and the two bantered about his management style and her boyfriend Josh Chan. They met with a potential client but Rebecca didn't get a contract. Nathaniel reminded her of the deadline and in response to Darryl and Rebecca mocking his daddy issues fired George . That night, Nathaniel teased Rebecca at a restaurant where she was having dinner with her fiancée and his parents. The next day Nathaniel was about to fire several employees wheh he was interrupted by Rebecca and Paula. Failing to meet the deadline, Rebecca pleaded with Nathaniel in private to reconsider his decision.
When Nathaniel insulted both her and Josh, Rebecca responded by chasing him with a pen. As Nathan struggled with Rebecca over the pen, the potential clients from the other day showed up. Despite the scene they witnessed they decided to hire the firm due. Having gotten the needed cash infusion, Nathaniel announced that everyone's job was safe for now ("When Do I Get to Spend Time With Josh?"). Sometime later, Nathaniel discovered a Treadmill desk in storage at the office and had it cleaned and installed in his office. As he excercised on the treadmill, he was interrupted by Daryl who made some inadvertent scatalogical references. Once Darryl left Rebecca showed up to tell him she was using her vacation days to take a trip back home to Scarsdale with Josh.
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