By now, ‘E’ should be U.S. Sen. Barack Obama’s least favorite letter in the alphabet.

Is he black enough?

Is he tough enough?

Is he experienced enough?

Is he electable?

Going into Thursday night’s caucuses, the Illinois Democrat is leading some Iowa polls and clearly is among the front runners nationally for his party’s nomination for president, along with Sen. Hillary Clinton, the first female candidate considered to have a realistic chance at the title.

It’s both heady stuff and uncharted territory.

“I think you’re absolutely right to identify this as both being about Barack and Hillary, the presence of a woman,” said Christopher Edley, Jr., dean of the Boalt Hall law school at the University of California, Berkeley.

Edley noted that Rep. Shirley Chisholm (1972), the Revs. Jesse Jackson (1984, 1988) and Al Sharpton (2004) had all tossed their hats in the ring, but until this year’s campaign, very few people ever thought that the leading candidates for the highest office in the land would include a woman and a minority.

“That is huge,” Edley told BlackAmericaWeb.com. “Obviously, you can say it’s long overdue, but it’s huge. All you have to do is look at the other side of the aisle in the Republican Party at that phalanx of white men."

“It sets the tone, freeing up the thinking about what is possible,” said Edley, a former professor of Obama’s at Harvard Law School and now an informal adviser to the campaign. “I think they help each other in that regard. His candidacy is made more plausible because his chief competition is a woman, and, conversely, her candidacy is more plausible because her chief competition is a black man.”

What makes Obama’s campaign different, however, is that it has an air of possibility that even the strongest supporters of Chisholm, Jackson, Sharpton and former Sen. Carol Moseley-Braun (who ran in 2004) -- and perhaps now former Rep. Cynthia McKinney, who recently announced her candidacy on the Green Party ticket -- never really believed.

“He’s a credible presidential package,” said Roger Wilkins, a history professor at George Mason University in Virginia who was an adviser in Jackson’s runs for the White House, especially during the 1984 run. “(Obama) excelled. He went to a very great university (Columbia). He went to what is considered the best law school (Harvard). He was an outstanding student there; he was president of the law review. Not only was he an extraordinary student, but you have executive abilities that you hone in the middle of a bunch of very smart people."

“These are already very substantial mainstream credentials that the other black candidates did not have. Even though Shirley had been elected to Congress, she was a woman and black in 1972,” Wilkins, an Obama supporter, told BlackAmericaWeb.com.

When Chisholm ran for president, the black community was far from united behind her. While she enjoyed strong support from many, including Rep. Parren Mitchell (D-Md.) and Rep. Ron Dellums (D-Calif.), it was an era of splintered politics -- as black militants turned away from the nonviolent, civil disobedience after Martin Luther King, Jr.’s assassination and moved toward a more confrontational style of politics. There were also murmurs within the black establishment that Chisholm should have deferred to a male candidate. Then there were those who resented what they saw as influence from the predominantly-white women’s movement -- especially the support of feminist leader Betty Friedan -- making the campaign more feminist than black.

At the Democratic National Convention in Miami ’72, with 151 delegates pledged to her, Chilsolm delivered a speech that expressed hope that future black candidates would prevail:

“I am a candidate for the presidency of the United States. I make that statement proudly, in the full knowledge that, as a black person and as a female person, I do not have a chance of actually gaining that office in this election year. I make that statement seriously, knowing that my candidacy itself can change the face and future of American politics -- that it will be important to the needs and hopes of every one of you -- even though, in the conventional sense, I will not win.”

Wilkins and several political scientists have said much of Obama’s success to date is directly tied to the campaigns of black candidates before him.

“In working in Jesse’s campaign, I thought that it was really brilliant to have a really brilliant black man running for president,” Wilkins said. “I never thought he would win, but it would crack minds open -- and the idea that blacks are smart enough to be president.

“What people saw in him was a narrow candidate, as a preacher and civil rights leader, but it inspired thought beyond the black community imagining a black person in the Oval Office,” said Wilkins. “It made the idea a less outlandish thing than it would have been in 1960.”

Jackson won five Democratic primaries and caucuses in ’84 and 13 in 1988, winning 29 percent of the primary votes.

Still, there are people who believe what Edley called “the Bradley factor” could stall Obama’s campaign.

When Los Angeles Mayor Tom Bradley ran for governor in California in 1982, all the polls had him leading handily, “but when people got behind the curtain, they couldn’t pull the lever” for him, Edley said. “The question is to what extent does that Bradley effect still an effect 25 years later? We’ll obviously know a hell of a lot more Thursday night and even more so after New Hampshire.”

Less than 4 percent of the nation’s elected officials are black, and 90 percent of them represent predominantly black and Latino constituencies, according to The Washington Post. There have been just three black U.S. senators (Ed Brooke of Massachusetts, Moseley-Braun and Obama) and two black governors (L. Douglas Wilder from Virginia, and curent Massachusetts Gov. Deval Patrick) since Reconstruction.

So if Obama is successful in Iowa, does that translate into more votes down the line this time? Is the possibility of a black president really more feasible than in years past?

“In terms of picking a candidate who has the best chance of winning, it’s more individual than public,” David Bositis, a senior research associate at the Joint Center for Political and Economic Studies, a black think tank in Washington, D.C., said in an interview last month about the value of Oprah Winfrey’s endorsement of Obama.

“If you look at experts who spend all their time following elections, a lot of them have a hard time picking someone who is going to win,” Bositis told BlackAmericaWeb.com. “So how are you going to know if the person you think is going to win is going to?”

Still, he said, making an educated calculation about who has the best chance based on personal observation and history isn’t just cynical voting.

“People’s knowledge, to some degree, is based on experience. If you’re in South Carolina, your experience is white people won’t vote for a black man. If you live in Massachusetts, you know white folks voted for a black governor (Patrick) and a black U.S. Senator (Brooke). If you live in Colorado, Colorado has had a number of black people elected statewide. It depends on where you are,” Bositis said.

But some of those states that might not be carried by a black man in the general election next November probably wouldn’t be carried by a woman either, Bositis noted.

“He won’t win South Carolina,” Bositis said, “but neither is Hillary. So who are you going to vote for? Hillary?”

“What I’m fearful of is conceivably, (Obama) could get the Democratic nomination,” Prof. Larry E. Davis, director of the Center of Race and Social Problems at the University of Pittsburgh, told BlackAmericaWeb.com in an earlier interview. “But when you throw the whole country in, white women haven’t been loyal (to the party). They have voted with men against affirmative action even though they were beneficiaries."

“Will they stay? Obama may be able to pull them for the primaries," Davis said, "but in the general election, will they stay with their husbands or boyfriends when they go to the polls?”

Davis and Bositis said they weren’t convinced Obama could win the general election, but they thought he made the race more interesting and challenging for all the candidates involved -- and that he has furthered the concept that a black man could someday become president.

Wilkins, however, sees things a little differently for Obama.

“Now this fellow comes along, and he’s clearly very smart and touches all the right bases. He’s been a community organizer, a civil rights lawyer, a constitutional law teacher and he has been a politician and he didn’t start at the top,” Wilkins said. “He’s paid his dues at the local level, including making a dumb mistake by running against (Illinois Rep.) Bobby Rush” and being soundly thrashed. “So when this man talks about the political process and what it takes, he has a good balance of community and political experience. And he’s so smart, he has churned this issue and he’s churned that issue over in his mind.”

Wilkins admits he has a somewhat personal connection with Obama.

“I grew up in a community that was away from a large black community” in Grand Rapids, Mich., said Wilkins, whose father died when he was nine years old, "and the issues of identity were very acute for me. I had to work them out and had a lot of false starts, but having it strengthened me as an adult and in my professional life.”

Looking at Obama’s background, he said, “you know he had to do a whole lot of complicated and acute introspection to figure out who he was and what he wanted to be.”

Obama was the product of an interracial marriage. His Kenyan father left the family when Obama was two years old. His mother remarried, to an Indonesian man, and moved the family to her new husband’s homeland. He had to learn a new language, a new culture and get used to a stepfather, all the while nursing the wound of abandonment.

While his father didn’t walk away from the family, Wilkins said, he understands a little of what Obama went through not having his father around, the subsequent adjustment to a different environment and sorting out his identity in the process.

“That’s a very complicated stew to go through in order to become complete,” Wilkins said.

The result of all that in Obama’s case, Wilkins said, is a “well-defined persona. He’s done all the heavy lifting to take on such a massive task, including his marriage to a very able and effective life partner. It’s more than just his wife. She obviously has brains to match his and has no-nonsense attitude."

“He brings to this a political service and personal sense of self that people find compelling,” Wilkins said.

Add to that the rough and tumble experience of community organizing in Chicago and dealing with Chicago and Illinois politics, Wilkins said, and Obama is more than tough enough for the campaign.

“Chicago politics ain’t beanbag,” Wilkins said. “He’s been around some really serious political blocks.”

Edley agrees with Wilkins' assessment of Obama.

“His journey has made him breathtakingly secure in who he is,” Edley said. “He has a centeredness about him that is unlike anything I’ve seen in other candidates with whom I’ve work in recent years, except Jimmy Carter.”

Whether Iowans see all that in Obama will be put to the test Thursday night.

According to Edley, Iowa is important, not just because it will show whether a large percentage of white people will vote for Obama, but because voters there see the candidates in a way that the rest of the nation’s electorate does not.

For the past few decades, Iowa and New Hampshire have been able to turn the “accident” of being the first scheduled votes of the primary season into a major opportunity to get to know the candidates better, perhaps, than anywhere else in the country because candidates spend far more time there, especially since the campaign season seems to start earlier and earlier in each election cycle.

“It’s an opportunity for candidates to go into retail politics,” said Edley, noting that candidates spend a lot of time stumping door-to-door, at small gatherings, meeting with voters personally in all kinds of venues and not spending tons of money on advertising in order to get their votes.

“I’ve been in 85 of 99 counties in Iowa,” said Edley, who was national issues director for former Massachusetts Gov. Michael Dukakis’ campaign in 1988. He said Iowans take politics very seriously and immerse themselves in the issues.

“What happens is, first of all, caucusing governs more interest in and activity in politics because you’ve got to be motivated to go out on Thursday night to your local caucus, stand up and say who you support and go stand in a corner with other supporters. Your neighbors know who you’re supporting and may ask you why, and it’s very different from the private, secret ballot model,” Edley said.

Next, independents and Republicans can show up at a caucus, register as Democrats at the door and participate. So getting the vote out is crucial.

And in the process leading up to caucus day, Edley said, the voters have had plenty of opportunities to ask questions and grill candidates on the issues.

“They are professional presidential candidate reviewers,” Edley said. “These folks in Iowa, they work hard at this; they are extremely sophisticated. They can talk about farm subsidies one minute and then ask the senator, ‘what’s your position on Burma?’”

He recalled a dinner with a group of hog farmers in 1988, where the topic switched from hog futures, protection of small farms and subsidies to a discussion of whether upgrading warheads for Trident nuclear submarines would really expand the Navy’s ability to protect a wider area.

“And the national reporters are in the back of the room ... waiting for you to screw up,” Edley said.

“Iowa and New Hampshire are very effective proving grounds for whether a person has the right stuff,” Edley said. “You have to have your stuff together to survive.”