that Toby is an attorney. Toby is a fan of the New York Yankees. He claims to have attended 441 games at Yankee Stadium. He also reveals his fandom of the New York Knicks and is once seen wearing a New York Giants hat in his office. At the White House Before joining the Bartlet presidential campaign, Toby was a professional political operative who worked for various campaigns including New York City Council seats, Bronx Borough President and U.S. House and Senate races. However, he had never been on a winning campaign before Bartlet's 1998 presidential bid. He says that he backs the candidates who should win, rather than those who will win, and is unapologetic about his low winning record. Once in the White House, Toby is rewarded for his work on the campaign, with Bartlet naming him Communications Director and senior domestic policy advisor. Later, it is revealed that Toby was not the president's first choice for the job, although Bartlet confides that he is grateful his first choice turned down the job. Of all the senior staffers, Toby is the most prone to clash with the President, being unafraid to challenge his judgment and question his actions when he feels Bartlet is not acting according to his true morality. When Will Bailey leaves the president's staff to work for the vice president, Toby interprets the move as a betrayal and develops an antagonistic attitude towards Will that never is truly fixed (they simply go from being constantly at odds to having little or nothing to do with each other, though Will is shocked and left near tears when a devastated C.J. tells him about the shuttle leak and installs him as the new Director of Communications). Similarly, when Josh leaves the White House to run a presidential campaign for Matt Santos, Toby views this as a betrayal and is extremely hostile to Josh until long after. His reaction is eventually explained with the revelation that his brother David, recently diagnosed with terminal cancer, committed suicide rather than live what time he had left: "He could have had years. But instead, he just dropped everything and walked away." Toby feels "walking away" is what Josh has also done. Josh later (successfully) moves to keep their friendship alive, and Toby keeps advising Josh as he tries to get Santos elected president. Toby's oldest friend in the White House is