Hillary Clinton faces some unusual and vexing problems as she pursues her party’s nomination for the presidency. Like everyone else in the campaign, she faces an unusually long road to Denver, fraught with running tape recorders and endless photographs and videos of her “bad side.” But unlike the others, she is forced to defend a lead she has built by being the presumptive nominee from the beginning, in effect playing a ball-control game from the opening kick-off, majoring on defense. By now, most people who care know that Hillary’s negative numbers (won’t vote for her…perceive her negatively) are essentially twice that of John Edwards and Barak Obama. This is an issue that must be addressed or else the Democrat power brokers will reject her as they did Howard Dean after his “I have a scream speech.” They will declare her unelectable and that will be that. The Democrat big money people are not about to miss this big opportunity like they did in 2000.

    But there are some pretty clear intangibles that dog Hillary as well. Over the last few months, she has referred back to the “two for one” mantra that Bill Clinton used in his first run for the White House in 1992. Her recent reference to Bill as a “worldwide ambassador” sent chuckles through many of us thinking about Hillary in the White House alone or the reverse, Bill “home alone” on a weekend night with nothing to do, flipping the remote control while looking at the telephone. The bottom line: Bill Clinton is not an undiluted asset for Hillary, for two reasons. First, as a woman she needs to be perceived as presidential, a Margaret Thatcher type, strong, tough, resolute, decisive, not needing to consult a man for advice. At times, Hillary has appeared to bring Bill into the picture when she was being attacked or felt she needed him, like in her famous “Kentucky Fried Hillary” remarks in Mississippi. Using Bill wrongly hurts her here, making her appear indecisive and needy. Secondly, Bill Clinton hurts Hillary on stage when she speaks. His presence simply reminds people how good he was and is at public speaking and Q&A, and he reinforces how mechanical and uncharismatic she is. Look for him to do a lot of campaigning alone because of this.

    Another hurdle for Hillary is the environment for change. It is huge. Not since the twelve years of Republican rule in the White House came to an end in 1992 has the desire for change been so palpable. Bumper stickers saying “had enough?,” discontent Republican conservatives, and the Iraq War all contribute to the “I’m sick of it” attitude among the electorate. This does not guarantee the White House for Democrats in 2008. Far from it. Presently, Rudy Giuliani beats all Democrat comers in national polls, a statistic that still reflects voter distrust for the Dems on national security. How Republicans will cope with this desire for change remains to be seen. Hillary’s problem is not just her defense of her Iraq War vote which she has all but repudiated. Her big negative? She’s the most establishment figure running for president. In an environment screaming for change, this hurts her and money will not change it.

    Enter Barak Obama. In an age which preaches “experience required” for being president, Barak Obama would normally be relegated to the middle of the list for VP candidates. But with Iraq, change in the air and President Bush’s bumbling speaking style, Obama fits a certain bill. Whether he fits the bill is another question. Obama is everything Hillary is not: articulate, short on policy specifics, inexperienced and an outsider. I watched him speak in New Hampshire three months ago and the room was filled with bearded white men literally on their tip-toes listening to him. He has been “right” on the war, from a Democrat perspective. He is raising money and closing on Hillary in the polls. Even if Obama falters, Democrats may turn to John Edwards rather than put forward an unelectable Hillary. Look for Obama to pass Hillary in second quarter fund raising which will raise a storm among the Democrat faithful. And the looming 527’s are just hankering to pour money into a bona fide anti-war candidacy.

    Will Hillary grind it out to victory? No one knows. But she has some large negatives looming on the horizon. These are just a few.

John Pendleton