"Of all of the Democratic possibilities that might have run, I think she's uniquely vulnerable to Trump because she symbolizes everything that he is telling people is wrong," political journalist Jeff Greenfield told David Axelrod on "The Axe Files," a podcast produced by CNN and the University of Chicago Institute of Politics.
"Anything she throws at him ... 'You don't know anything!' 'Oh well, you knew everything -- that's why you voted for the war in Iraq and screwed up the Russia reset and Syria.' 'You're corrupt!' 'Really? How much money have I taken from Goldman Sachs to give speeches?' " Greenfield said.
"Many Democrats voted for the war in Iraq. She is perhaps the only one who made an allegation that Saddam Hussein was somehow involved with al Qaeda and 9/11," Greenfield said. "Everybody changed their mind about gay marriage. Almost everybody. But you look at what she said about that when she was on the other side, she talked about one man, one woman
marriage as a building block, a foundation block of western civilization. When you commit yourself that strongly to position A, then a couple years later as the shift in wind goes on and you're in position not A, it gets harder."
Further complicating Clinton's chances of defeating Trump this fall, Greenfield noted that a large bloc of disgruntled voters may feel emboldened by the opportunity to elect the controversial real estate mogul.
"I think there's a period every so often in American political life -- not frequently -- when particularly aggrieved voters learn they can do something they didn't know they could do. That becomes a hugely powerful force," Greenfield said, citing the 2003 recall of California Gov. Gray Davis as an example. "Beyond any particular policy issue or is there going to be a terrorist attack, that's the wild card. That's the black swan for me."
Despite Clinton's vulnerabilities, Greenfield said that he would still wager on her to win the White House if given acceptable odds.
"If you gave me a certain amount of disposable income and asked me how to bet it, I would bet it on Hillary. But if the odds were right, I would want to have some back," he said.
Greenfield, who writes for The Daily Beast and Politico and previously worked at CNN, CBS News, ABC News and PBS, stated that Trump has benefited this year from favorable media coverage.
"When you put a candidate on for an hour unfiltered, you might as well be state television in Havana putting on a speech by Fidel," he told Axelrod. "I think the decision by the networks to let him phone it -- in literally phone it in -- because that meant ratings was a gift to him. It let him campaign strictly on his terms. I think some of the interviews I saw with him were embarrassing and some of them were very good and very tough."
To hear the whole conversation with Greenfield, which also touched on his work for Robert F. Kennedy in the 1960s, the changing media landscape, and much more, click on http://podcast.cnn.com
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