Against competition from the likes of Ari Fleischer and Mike McCurry, it is tough to suggest that Robert Gibbs was the worst White House press secretary in modern times. Then again, the spokesman for an administration that admits it cannot seem to get its message across on even the most basic levels, would have to be in contention for the title.

Certainly, few press secretaries have ever done more harm to a president they could so easily have helped.

Gibbs, who announced today that he will exit his position in early February, following in the footsteps of much of the rest of the team that came to the White House from the 2008 campaign, was never a particularly good communicator. A bland and forgettable player during a long presidential run when the focus was almost exclusively on the candidate, Gibbs emerged shortly after the election as the face of the new administration. That proved to be politically disastrous for the president. Thin-skinned and prone to attacking friendly critics, he did more than anyone except former White House Chief of Staff Rahm Emanuel to create and expand the progressive "enthusiasm gap" that so harmed Democrats in the 2010 election cycle.

Noting the "contempt" that Emanuel, Gibbs and other departing administration aides displayed for grassroots Democrats—and progressive values—former Democratic National Committee chair Howard Dean got the sentiment right when he said Wednesday: "As they say, don’t let the door hit you in the you-know-what on the way out.”

Gibbs will be remembered, in particular, for his harsh criticism of what he termed "the professional left," which, like Emanuel’s dismissal of serious healthcare reformers as "retards," exposed the anger of Obama’s inner circle at the principled activists and groups that played such a pivotal role in securing the 2008 president nomination for a freshman senator from Illinois. Gibbs was one of the politically naïve players who believed that they had "created" Obama as some sort of media phenomenon, and always failed to recognize that their candidate was nominated largely because he was seen as the "left wing of the possible" among the major contenders in 2008.

That misread meant that every time Gibbs opened his mouth, he widened the gap between Obama and the progressive base that the president could not afford to take for granted. Even when Obama and others in the White House attempted to build bridges, Gibbs and Emanuel burned them. And the rest is history—the history we are now living as Republicans take charge of the House and game the administration on issues such as tax policy.

Whoever replaces Gibbs will be an improvement.

But that improvement will best serve Obama if it comes as part of a serious change in direction when it comes not just to how the administration communicates but how it relates to the base. Some potential press secretary picks—such as Jay Carney, a former reporter who has worked closely with Vice President Joe Biden—would be better than others. Ultimately, however, the internal problems facing the administration will require that the new press secretary be aligned with a strong new chief of staff.

The fact of that need has heightened speculation about the prospect that veteran Chicago pol William Daley—a manager and aide to many past Democratic campaigns who is generally seen as someone who "gets" the dynamics of the party—might take over as chief of staff. 

Former Democratic National Committee chairman Howard Dean, who has been increasingly critical of the administration’s approach to the base, is taking up Daley as a "huge plus" for the Obama administration.

Dean acknowledges that Daley is a more conservative player than the former Vermont governor and 2004 presidential candidate might pick. In fact, Daley is so closely tied to big banks and corporations, especially some telecommunications giants that are on the wrong side of media issues, that the former DNC chair might come to regret headlines that suggest he is endorsing Daley for the top White House post.

But Dean is trying to make a point about how this White House operates. And it is that there is a need for "adult" supervision. He argues that Daley is "a grown-up who doesn’t treat people like they don’t know anything and you know everything."

While Dean did not criticize Gibbs or Emanuel by name, the reference to Daley as a "grown-up" came in response to a question asked about Gibbs’s jibe at the "professional left."

But Dean did say, "Disrespect breeds disrespect." And there was never any doubt that Gibbs disrespected progressives. Worse, Gibbs failed to understand how much Obama needed the grassroots activists and voters who elected him. As such, he did not merely fail the base. He failed the president he was supposed to serve.