(CNN) -- Sen. Barack Obama's campaign Monday tried to draw a parallel between Sen. John McCain's involvement in the nearly 2-decade-old "Keating Five" scandal and the current economic crisis.
A graphic from an Obama documentary ties Sen. John McCain to Charles Keating.
The Obama campaign released a 13-minute documentary called "Keating Economics: John McCain and the Making of a Financial Crisis."
In the documentary, the narrator says that "the Keating Five involved all the things that have brought the modern crisis" and that McCain "has not learned the lessons and has continued to follow policies that are going to produce a disaster."
The documentary includes narration from William Black, a bank regulator at the time, and video footage of testimony from the 1990 Senate hearings on the scandal.
McCain was investigated as being one of five senators, dubbed the Keating Five, who met with regulators on behalf of Charles Keating, the owner of an Arizona savings and loan. Fact check: Did McCain intervene on behalf of Keating?
Keating later went to prison for fraud committed while he controlled Lincoln Savings & Loan.
In the documentary, Black says Keating "was, and is, a very nasty, fraudulent guy" who "bought and sold politicians."
Black also says Keating advised McCain and encouraged him to pursue an anti-regulatory policies.
The Senate Ethics Committee cleared McCain in 1991 but said that he showed poor judgment in his efforts for Keating, who had been a major contributor to McCain's campaign. McCain later turned over $112,000 in campaign contributions from Keating to the U.S. Treasury. Watch how the gloves are coming off on the trail »
The documentary debuts two days after Alaska Gov. Sarah Palin accused Obama of "palling around with terrorists who target their own country" for his ties to Bill Ayers, a founding member of the radical Weather Underground. Fact check: Does Obama have ties to Ayers?
Weather Underground was involved in bombings in the early 1970s, including attacks on the Pentagon and the Capitol. Obama was a child at the time of the bombings. iReport.com: Shame on McCain campaign
Obama and Ayers, now a university professor, have met several times since 1995, when both worked with a nonprofit group trying to raise funds for a school improvement project and a charitable foundation. CNN's review of project records found nothing to suggest anything inappropriate in the volunteer projects in which the two men were involved.
Obama on Monday said, "The American people deserve better."
Speaking to CNN contributor Roland Martin on the nationally syndicated radio program the "Tom Joyner Morning Show," Obama said, "Now they're trying to use this as guilt by association. And they've explicitly stated that what they want to do is change the topic because they don't want to talk about the economy." Watch how Obama responds to the attacks »
Palin on Monday continued her attacks on Obama and his political relationship to Ayers.
At a rally in Clearwater, Florida, she said Obama was being "less than truthful" about his ties to Ayers.
"His own top adviser said they were 'certainly friendly.' ... I am just so fearful that this is not a man who sees America the way that you and I see America -- as the greatest source for good in this world," she said.
McCain aides said bringing up Obama's connection with Ayers is part of a strategy to raise doubts in voters' minds about whether they can trust the Democratic presidential nominee and highlight how little they know him.
The aides also said the campaign would try to raise questions about Obama's ability to handle the economic crisis. iReport.com: What issues do you want to hear during Tuesday's debate?
"With economic news at the top of voters' minds, it makes sense for the top of the ticket to talk about Obama's failures and lack of credibility on the economy," one McCain aide said.
As part of the continuing attack on Obama's judgment, the McCain campaign released a new ad Monday that tries to paint the senator from Illinois as a "dangerous" candidate by highlighting comments he made about Afghanistan more than a year ago. McCain ad targets Obama's remarks on Afghanistan
The McCain campaign said the key difference between McCain and Obama is that the senator from Arizona has been open about his past ties to Keating.
"John McCain has been open and honest about the Keating matter, and even the Democratic special counsel in charge recommended that Sen. McCain be completely exonerated," spokesman Brian Rogers said in a statement.
There may be some pitfalls in going negative, especially among independent voters who tend to be turned off by such negativity, analysts said.
"I think some of the terrorist charges by association will strike voters as very far-fetched and could create a backlash. But, in any case, what it does is it means the campaign is talking about something other than the economy," said Bill Schneider, a CNN senior political analyst.
Obama also could be running a risk, Schneider said. The Democrat has another ad that tries to paint McCain as "erratic" and "out of touch," with quotes from newspaper editorials.
"He was clearly referring to McCain's behavior last week when he suspended his campaign, went back to Washington, tried and failed to broker a [bailout] deal which eventually did come to pass, then came back into the campaign," he said.
"But some people are angry because they think erratic is some kind of a reference to McCain's age and that is unfair."
CNN's Dana Bash contributed to this report.