Toby is a fan of the New York Yankees baseball team. In Posse Comitatus, the show's third-season finale, first airing on May 22, 2002, he claimed to have attended 441 games at Yankee Stadium. If he saw his first game there at the age of seven, in the 1962 season, and the show progresses in real time, this works out to about eleven games per season, though it is not clear if he could keep up this pace once he began working at the White House.
Toby has been a professional political operative almost all of his life. His political experience includes work on one city council campaign, two Congressional races, a Senatorial and a gubernatorial race and a national campaign. Toby had never won an election until the Bartlet campaign.
- To be West Wing-wikified
In addition to being in charge of the message for the Bartlet administration as the Communcations Director, he is a Senior Domestic Policy Advisor to the President.
Toby can be seen throwing a ball (most likely a Spaldeen stickball from his memories of growing up in Brooklyn) against the wall as a way to brainstorm in more than one episode.
When he writes, especially when he writes important speeches, Toby apparently likes to have pie on hand at all times. 
Toby gets along well with his assistants, Ginger and Bonnie. He also has a close relationship with his first Deputy Communications Director, Sam Seaborn, which is occasionally tested through the first four seasons.
Toby's ex-wife, Andrea 'Andie' Wyatt, is a U.S. Congresswoman and liberal Democrat from Maryland. During the fourth season, it was revealed that Toby and his ex-wife had conceived twins together. His ex-wife is later sued by a right wing group on grounds that her nondisclosure of her pregnancy during her campaign for re-election constituted election fraud. She has repeatedly turned down Toby's proposals for re-marriage. Toby and Andrea's children were born the same day that Zoey Bartlet, President Bartlet's daughter, was kidnapped. They are named Huckleberry and Molly. Huck is named after his maternal great-grandfather, and Molly is named after the Secret Service agent who was killed attempting to prevent Zoey's kidnapping.
Toby once had a crush or "a touch of the poet", in C.J.'s words, for U.S. Poet Laureate, Tabatha Fortis.
Near the end of Bartlet's second term, Toby leaked classified information to the press regarding the existence of a military space shuttle. His reasons for doing so stemmed from a crisis in space involving trapped orbiting astronauts and his own reluctance at using space for military purposes. In any case, it is unclear where he learned this information. It is possible that he learned it from CJ Cregg, or from Leo McGarry, neither of whom was authorized to reveal it to him. It is also possible that his late brother David, or David's widow, told him of its existence. Regardless, Toby has never revealed who told him about the shuttle's existence, although he has intimated that it was not his brother; little attention appears to have been paid to Toby's sister-in-law, though. (In "Welcome to Wherever You Are", he told his ex wife, who suggested naming the brother as his source, I will not defame my brother's name when he had absolutely nothing to do with it.)
This leak causes Bartlet to fire Toby, and the president's anger and sense of betrayal is massive. Toby is also indicted for leaking the information, and faces a lengthy prison sentence should he be convicted. He refuses to cut a deal and name his source however.
After leaving the West Wing, Toby seems to spend most of his time preparing his legal defense and giving depositions. However, he does find time to covertly and effectively advise Josh on the Santos campaign. He also attends Leo McGarry's funeral, although he must sit in the back and wait to leave until the president has left.
As President Bartlet's final act in office, he signs a presidential pardon for Toby, which saves Toby from prosecution, and at least partially heals their fractured relationship.
By the time of the dedication of the Bartlet Presidential Library, they have clearly reconciled. At this point, Toby teaches at Columbia University and considers it "not a bad place to spend time."
- He attended the City College of New York, but his undergraduate major or any postgraduate degrees are unknown.
- Political Campaign Consultant for the New York City Council
- Political Campaign Consultant for the Bronx Borough President
- Political Campaign Consultant for the US House of Representatives
- Political Campaign Consultant for the US Senate
- Political Campaign Consultant for the New York Gubernatorial race
- 1997-1998 : Communications Director for the "Bartlet for America" presidential campaign
- 1999-2006 : White House Communications Director and Senior Domestic Policy Advisor
Behind the scenes
to be added
| White House Communications Director|
1999 – 2006