"Many of us, including myself ,who are lifelong Democrats are really discouraged by the president," Siskind said. "I hope a woman gets it."
But Siskind said she fears that a woman could be appointed for the optics of the choice. The White House would benefit from a woman in a public, powerful role within the administration, she said, but only if she is given the tools to survive and succeed in that role.
"I'm very concerned that they would send her out to slaughter," she said if a woman was chosen mostly for the sake of appearances.
Dana Perino, press secretary to President George W. Bush, says that if the White House is considering choosing a woman, it should take a little message management to make sure that people know why she was chosen.
"If they do choose a woman, they don't want to diminish her accomplishment right out of the gate with some who'll think she was chosen just because of her gender," Perino told ABC News.
In a long line of male press secretaries, there have only been two women in the role: Dee Dee Myers, serving under President Bill Clinton and Perino.
Robert Gibbs first started working with Mr. Obama when he was still a Senator, making him not only a valued spokesperson over the years, rising with Obama's power, but a trusted advisor and friend of the president. The future White House press secretary may not have such a relationship at first.
"I do think I have, because I've been here so long with him -- or have been with him so long, that there is a uniqueness to that," Gibbs said of his relationship with the commander-in-chief.
Press secretaries over the years have had to strike a balance. They are often not just the official spokesperson; they are friends and informal advisors to the president, much as Gibbs has been.
President Carter's press secretary, Jody Powell, served dueling roles in the 1970s. He and Carter were friends – even bunking together during grueling nights on the campaign.
George H.W. Bush's press secretary, Marlin Fitzwater, dined with the president and his wife often at the White House and on the road.
But a close friendship with the president does not always lead to job security as a press secretary. Dee Dee Myers, the longtime press secretary for President Clinton, was let go, replaced by a more savvy spokesman, Mike McCurry, in Clinton's second term.
There have been only a small handful of press secretaries brought on staff to just be a spokesman, most recently Tony Snow, who was a conservative pundit hired as President George W. Bush's third press secretary.
Gibbs says that he doesn't think anyone would appoint his successor without granting the person the ability to find out the answers properly for press, whether that is to go see the chief of staff, the senior advisors, or the president or the vice president when they needed to.
"It's important to be able to walk into his office and say, 'Sir, I need to get your opinion on this,'" Gibbs said.
Finding the right balance, and cultivating a natural friendship and trust that comes from the role is an important one – one that might be easier to achieve with someone already working within the gates of 1600 Pennsylvania Avenue.
"This is a tough place to work," Gibbs said last week, knowing that being chosen is likely the easy part of the job.
ABC's Ann Compton contributed to this report.