The McCain campaign took a broad swipe at portraying Obama as an elitist with its "celebrity" ad in which pictures of Britney Spears and Paris Hilton flashed across the screen shortly before Obama was pictured.
Vice presidential candidate Sarah Palin included a direct series of jabs at Obama in her convention speech, mocking the time he spent as a community organizer and focusing on the "bitter" quote.
"I guess a small-town mayor is sort of like a 'community organizer,' except that you have actual responsibilities," said Palin. "I might add that in small towns, we don't quite know what to make of a candidate who lavishes praise on working people when they are listening, and then talks about how bitterly they cling to their religion and guns when those people aren't listening."
She added, "We tend to prefer candidates who don't talk about us one way in Scranton and another way in San Francisco."
But McCain's words and actions have detracted from such a message. After it was revealed he was wearing $520 Ferragamo loafers, McCain last month couldn't recall for an interviewer how many homes he owned. At a faith forum, when asked for a "specific number that would make someone "rich" instead of "middle class," he said, "How about $5 million?"
Newsweek reported last weekend -- despite McCain having said he had bought American cars "literally all my life" -- that three of the 13 cars he owns are foreign-made. Last week, McCain repeated his refrain that the "fundamentals of our economy are strong," even after financial panic had started to spread through Wall Street and beyond.
Mark Brewer, chairman of the Michigan Democratic Party, said the most recent revelation about McCain's cars helps fashion a "powerful issue" for Democrats to highlight.
"The cumulative effect of all of this is somebody who is out of touch," Brewer said. "For people struggling to hang on to their homes or have a car, this is somebody who just doesn't relate."
Carrick, the Democratic strategist, said Obama aides have been more effective in driving their message of "elitism" because McCain has given them more concrete examples to work with.
"The McCain attack is based on an image only -- that's elusive. Image is in the eye of the beholder," he said. "But seven houses, and he didn't know he had seven houses? Thirteen cars? That all is memorable stuff."
But Obama has to be careful in pushing such a message. McCain can fall back on a personal story "that many Americans find compelling," Zelizer said.
Indeed, McCain cited his time as a POW when asked by Jay Leno about the number of houses he owns.
"I spent 5½ years in a prison cell. I didn't have a house, I didn't have a kitchen table, I didn't have a table, I didn't have a chair," McCain said. "I spent those 5½ years not because I wanted to get a house when I got back home."
Both candidates are personally wealthy, though McCain -- whose wife inherited a lucrative beer distributorship -- is considerably more well-to-do. This week Roll Call ranked McCain as the 13th-wealthiest member of Congress, and Money magazine has pegged his net worth at about $40 million; the magazine estimated Obama's net worth at $1.3 million.