West Wing: The 5 Worst Things Josh Lyman Ever Did (& The 5 Best)

Throughout its seven seasons, fans fell in love with Josh Lyman, the dedicated and hardworking Deputy Chief of Staff for the Bartlet Administration. With his boyish charm, charisma, and undying desire to do good, he was an incredibly popular character even twenty years after the show aired. While a popular character, Josh was often a bully and sometimes did problematic things.

Despite his intentions, Josh Lyman’s flaws and negative actions created difficulties for the rest of the staff. While his choices were often questionable, Josh Lyman remains a (mostly) beloved character by West Wing fans.

Best

Hiring Charlie

Josh is hiring a body man for the President and is sent Charlie who is merely looking for a job as a messenger. After hearing Charlie’s story about losing his mother and raising his sister on his own, Josh sees something special in Charlie. Charlie was one of the most likable West Wing characters and was one of the best staffing choices Josh ever made.

Charlie was not only a fan-favorite character, but he also made a huge impact in the day to day of the White House. He was an incredibly hard worker and was eventually promoted to work with CJ when she became Chief of Staff. While he started as the President’s body man, he became a de facto member of the Bartlet family.

Encouraging Santos To Run For President

Josh was being recruited by both Hoynes and Russell to manage their Presidential campaigns. Josh struggled with this decision because he didn’t feel like either of the options was good for the country. With Leo’s guidance, he decided to find a candidate to run that lived up to their standards. Josh found Matt Santos, a smart congressman who was quitting politics, and encouraged him to run.

Santos was a much better candidate than both Hoynes and Russell. Hoynes had many sex scandals throughout his time in politics and was tied to big oil. Russell had no real policy initiatives and was propped up by those around him. Santos had big ideas for the country with his strong education and healthcare policies. Santos truly lived up to the honorable President Bartlet fans loved for seven seasons.

Supreme Court Justices

Josh and Toby are working to fill an empty seat on the Supreme Court. They want to fill the seat with the liberal Evelyn Baker-Lange but are coming up against opposition who will only confirm a moderate justice. After talking with Donna, Josh gets the idea to compromise and allow Republicans to pick a Supreme Court Justice if they confirm Evelyn Baker-Lange as Chief Justice.

Josh and Toby get to confirm the first female Chief Justice of the Supreme Court, which is a huge victory. Additionally, this is one of the few times where Josh can set aside politics and work with Republicans across the aisle to get things done.

Trying To Make College Cheaper

At the end of the episode 20 Hours in America, Donna has snapped at Josh and Toby for their insensitive behavior. While they give her some space, they come across a man who was touring colleges with his daughter. After talking to the father, Josh and Toby come up with the idea to make college cheaper by making tuition tax-deductible.

Toby and Josh often felt held back by the red tape of the political system. They felt they had to compromise their beliefs and goals to get small things done. This is one of the few times where Toby and Josh get to fight for policies they truly believe in that will help the average American. While they aren’t able to pass the legislation, the conversation lights a new fire under Josh and reminds him of what matters.

Finding Sam

Two different times throughout the series, Josh is the reason Sam comes to work a the White House. He convinces Sam to leave his high-paying legal job in New York to join the Bartlet campaign as a speechwriter. In a parallel moment in season seven, Josh finds Sam in Los Angeles and convinces him to come to be Deputy Chief of Staff in the Santos Administration.

Similar to Charlie, Sam helped keep the Bartlet Administration afloat. He was young and wide-eyed with many wonderful ideas to make the country a better place. His beautiful speech writing helped elect President Bartlet multiple times, even when he was a relatively unknown candidate and again amid the MS scandal. He was the backbone of the administration and many fans believe Sam would’ve made a great President. Sam would not have been in his role without Josh Lyman.

Worst

Making A Senator Change Parties

Josh is in the news as the 101st senator for his political prowess and ability to get legislation through the senate. Meanwhile, he is also coming to blows with a moderate Democratic senator who is looking for funding for a missile launcher. Josh berates the senator so much that he decides to switch parties and become a Republican.

This is Josh’s worst political move throughout the entire series. Josh struggles to work with those that don’t agree with him and that he can’t bully. This leads him to become a political pariah and forces Leo to bench Josh for several episodes, including replacing him in the budget negotiations. This deeply impacts Josh and his view of his job.

Relationship With Amy

Josh’s relationship with Amy was highly controversial and was an unresolved West Wing storyline. Some fans believed she was a poorly written and unlikeable character, while some believed that she was his true soulmate and complimented him the best. Despite the controversy, Josh treats Amy very poorly throughout their relationship.

After the two come to blows over a welfare vote. Amy mobilizes to tank the vote, while Josh mobilizes to pass it. Josh wins and Amy ends up losing her job. While Amy is upset about losing her job, it is Josh, the winner of the situation, who is upset with Amy forever trying to lose the vote in the first place. Amy was doing her job, just like Josh, but Josh can’t handle her going up against him. This is one of many instances where Josh’s immaturity impacts his relationships.

Elitism Towards The Average Voter

In the episode, 20 Hours in America Josh, Toby, and Donna get left behind by the campaign bus and get stuck in Indiana. As one of the worst friendships on West Wing,  Josh and Toby spend the entire time desperately trying to get back to Washington and fighting about the campaign. The two spend the episode fighting about what matters to the average voter while ignoring all the average voters around them.

Both Josh and Toby’s elitism is at an all-time high in this episode. Instead of thinking and talking to all the Indiana locals who helped them get back to Washington, they bicker at each other and judge the people around them. They are incredibly rude to the many people who helped them and ignore the actual issues going on with the voters.

Reparations Conversation

Josh is meeting with a candidate for assistant attorney general for civil rights, Jeff Breckenridge.  After Breckenridge gave a quote advocating for reparations on the dust jacket of a book, Josh and Leo are concerned that he will bring up his stance in the confirmation and that it will reflect poorly on the Bartlet Administration.

Josh’s attitude towards Breckenridge throughout this episode is at best rude and at worst aggressive. While the meeting was merely to discuss his senate confirmation, Josh is unable to address the history of racism Breckenridge is discussing. He completely ignores Breckenridge’s point and even compares slavery to the Holocaust. His inability to decenter himself and his perspective to listen to the people around him is a persistent problem and is on display in this scene.

Treatment Of Donna

While many fans loved Josh and Donna’s relationship, it remains highly controversial. As her boss, he often tried to ruin her dates and relationships with other men. While his explanations to Donna served to inform viewers about complex policies, they often came off as pretentious and mansplaining. He regularly shamed Donna for her choices in men and lack of education.

Most egregiously, Josh refused to support Donna’s career aspirations. He mostly refused whenever she asked for more work and ignored her when she tried to talk to him about a promotion. After she leaves for a better opportunity, he holds it over her and refuses to hire her on the Santos campaign even though she is more than qualified because she left him.