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Josh decides that he doesn't want Hoynes (or current Vice President Bob Russell) to be President, and instead convinces Texas Congressman Matt Santos to run for President, much in the same way Leo Mc Garry recruited Bartlet eight years earlier.

Josh leaves his position at the White House to run Santos's presidential campaign, leaving his legislative portfolio to be taken up by Clifford Calley, a move encouraged by Leo after he and later C. notice that Clifford's personality and his skills are not unlike Josh.

A largely unspoken friendship, and romantic tension, exists between the two for the majority of the series.

However, Hoynes's tendency to go against Josh's advice, and to prioritize politics over Hoynes' own ideas and convictions, frustrates Josh.Thirteen weeks before the New Hampshire primary, Josh receives a visit from Leo Mc Garry, an old friend of his father's.At Leo's request, a skeptical Josh travels to New Hampshire to hear Bartlet speak.In researching the role, Whitford said he found former Clinton communications director George Stephanopoulos's book All Too Human very helpful, "just because it gave a sense of the sort of smell and the texture and the level of intimacy with the president, which I was just unaware of." In the Season 1 episode, 'Mandatory Minimums', Josh is called "Rambo" by one of the staff after an intense telephone conversation.In other instances, the character is said to be based on former Clinton advisor Paul Begala who notes that some of Josh's experiences in the first season are some of the same experiences he went through.

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