The West Wing is a fan-favorite political drama about the White House senior staff in the fictional Bartlet istration. The series defied the old tradition of portraying politicians as either corrupt Machiavellian crooks or incompetent paper pushers, instead depicting people in government as both competent and virtuous, using their power to help others.
Despite the characters generally having good intentions, they still succumb to their own human failings. Sometimes these failures have major political ramifications, leading to widespread destruction that impacts tens of thousands of peoples' lives. These are the worst things that each of the main characters did on The West Wing.
Sam: Oil Spill
Sam Seaborn is the young charismatic Deputy Communications Director who writes speeches for the Bartlet istration. His most memorable screwup is at the start of the series, when he hooks up with a girl who he later learns is a high-class escort, resulting in a scandal that puts his bosses at risk and causes tabloid reporters to harass the young woman. However, that's not his most grievous sin.
Before ing the Bartlet Campaign, Sam worked for the law firm Gage Whitney Pace, where he helped an oil company obtain a fleet of ships he knew would fail. When one of the ships crashed and caused an oil spill, he was directly responsible not just for helping the oil company cause this disaster, but for protecting them from any legal repercussions.
Toby: Treason
Toby Ziegler is the Senior White House Communications Director for the Bartlet istration, as well as the moral com pointing True North at all times. Series creator Aaron Sorkin has said that Toby is the one who holds President Bartlet able.
In the final season of the show, Toby its to having leaked classified information central to US national security in order to save the lives of three astronauts - one of whom is not American. This is an example of putting human lives over the bureaucratic national interests of his own country. Actor Richard Schiff who plays the character has said he does not believe Toby is guilty, but if that's the case, then Toby lied to protect whoever is responsible.
C. J.: Abandoning Her Moral Com
C. J. Cregg is the White House Press Secretary who eventually replaces Leo as the Chief of Staff. She is one of several strong women on the show who wield their power with poise and competence while continuing to advocate for moral decisions, even when it is politically inconvenient. She champions women's rights in the Middle East, argues with Leo when he tries to suppress an EPA report, and confronts the Vice President about his affairs.
Unfortunately, after replacing Leo as Chief of Staff, she begins to compromise her values, being rude to those she loves, including blowing off Danny Concannon as he's in the middle of proposing. She also throws Toby under a bus over treason, then later comes by his apartment and flirts with him.
Leo: War Crime
The White House Chief of Staff, Leo McGarry, has his fair share of personal demons. Beyond his struggles with addiction, he has business deals with army contractors and pharmaceutical companies that are guilty of illegally (and legally) engaging in shady affairs, while he suppressed environmental findings to promote "clean coal" - a term for something that does not exist.
His worst crime was committed decades before the events of the show, when flying with the Air Force. On one of his missions, he hit a civilian target. While the US military covered him, international law is pretty clear on the topic.
Josh: Abuse
Josh Lyman is one of the most interesting characters on the show because he is not virtuous, but nor is he a bad man. At his core, Josh is a fighter, a political brawler who will throw down with both Democrats and Republicans to help serve his boss's agenda. While he is incredibly good at his job, Josh is not as smart as the people he surrounds himself with; he's just a man who gets results. In a word, Josh Lyman is a bully.
This is his greatest sin. He mistreats his staff, his friends, and his loved ones. He has also invoked racist, sexist, and homophobic speech on occasion.
Donna: Compromise Congressional Investigation
Donna is Josh's assistant. She is loyal to a fault, faithfully serving Josh's every whim, whether ordering plane tickets for him to go home and see his family during the holidays or ordering his lunch to the exact overcooked specifications he demands from a cut of beef.
At one point, Donna begins dating Cliff Calley, a man who works for the House Oversight Committee, while the House is investigating Leo McGarry. Cliff's relationship with Donna puts Leo in jeopardy when she lies under oath during the investigation.
Annabeth: Violate Consent
Annabeth Schott is a character who s the cast later in the series, taking a job as the Deputy Press Secretary under Toby Ziegler when he takes over C. J. Cregg's Press Secretary duties after her promotion to Chief of Staff. Annabeth's main job is coaching people on how to look, act, and speak in front of others to get the desired impact they seek.
At one point, Annabeth helps prepare the First Lady for a NASCAR rally, but conceals the fact that one of the NASCAR drivers will kiss her the First Lady. Needless to say, this is a violation of consent.
Vinick: Nuclear Disaster
Arnie Vinich is one of two candidates who run for President in the 2006 Presidential Election, the other being Matthew Santos. Santos does not have any skeletons in his closet, or at least none the show ever explores (though there are hints his brother is a less than scrupulous character). The Republican Nominee, Arnie Vinick, is not quite so clean.
Beyond the racist politicking and homophobic messaging the Vinick campaign uses, one of his core values is a belief in nuclear energy. A plant he pushed to have opened begins to have a meltdown during the election, resulting in the surrounding area being evacuated.
Charlie: Endanger the President
The President's body man, Charlie Young, is a virtuous, intelligent, hardworking guy. He is possibly the most moral person among the entire West Wing cast, aside from maybe Toby. At the start of the series, he is raising his younger sister alone while working 20+ hour days in the White House and studying to go back to school.
So what is it that Charlie does that is so bad? Absolutely nothing. But when he dates the President's daughter Zoey, white supremacists target the young couple, shooting the President in the process. The worst thing Charlie does is merely to stand near his boss in a world so broken and racist that both are shot at.
Jed: Political Assassination
Jed Bartlet is the President. He is also a devout Catholic, a Nobel Prize-winning economist, a Classical historian, and a loving father and husband. His job requires him to make impossible decisions every day, the sorts of decisions that often come with body counts.
One decision he makes is to order the illegal assassination of a foreign dignitary, Abdul Shareef, the Minister of Defense to the fictional country of Qumar. While Shareef had funded terrorist attacks against the US, extralegal killings are just a loose attempt to justify murder for political gains. Of course, this would hardly be the first time a US President ordered the assassination of a foreign political enemy, but Jed himself has condemned these actions, so he knows that killing Shareef is unethical.