If Josiah Bartlet was the West Wing's Lear/Macbeth/Richard, then Tobias Zachary Ziegler was the conscience of the king. Brilliant, acerbic, unrepentantly liberal, Toby was a New York Jew with a long track record of backing the wrong candidates for the right reasons. He was a crusader, an unhappy warrior armed with ideals and a fountain pen. In Jed Bartlet he found a man he could believe in, a flawed diamond in a world of cubic zirconium. Toby chipped away at those flaws in a relentless attempt to shape the President into a more perfect champion of his own agenda, and the hammer-and-tongs dialectic between the two yielded some of the best scenes on a show full of great scenes.
Inhabited fully by the gifted Richard Schiff, Toby was a tragic figure, steeped in frustration and discontent. He suffered from that worst liberal distemper, the knowledge that he's smarter than everyone else, and if only everyone agreed with him, the world would be a vastly better place. He was rigid in his ideology, uncompromising in his values, and perpetually scowling. As his ex-wife, Congresswoman Andrea Wyatt, observes, he was "too sad". His work siblings CJ and Josh seemed able to crack that despondence on occasion, and the birth of his twins provided a glimpse of the deep, well-guarded reservoir of love within him. One of Toby's finest scenes came early on, when he learned that a homeless veteran died wearing a coat of Toby's given to Goodwill. In typical Ziegler fashion, Toby used the power of the White House to arrange for a military burial at Arlington with full honors. It highlighted Toby's implacable adherence to what he considered right, as well as the dynamic between him and the President. Bartlet knew it was right, too, but existed in the context of political reality that he could not ignore as readily as his lieutenant.
Eventually, this impulse proved Toby's downfall, as he leaked information about a secret military space shuttle to the press to pressure the Pentagon to rescue astronauts in distress. Toby's younger brother, after all, was an astronaut who had recently killed himself during his battle with cancer. Toby's service to his President and his country ended in disgrace, but that didn't cheapen the years of great speeches, both written for others and spoken himself, and the withering critique he constantly leveled at those willing to forsake the cause. Toby was a poker-playing, cigar-smoking, bourbon-drinking throwback to an earlier incarnation of political operative, and an unlikely yet visionary architect of a future he thought he alone knew.