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Hillary Clinton's guilt-by-association ad lives in a glass house filled with convicts

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In an election where Americans are clamoring for more civility and more substance, Hillary Clinton's new television ad intimating that Donald Trump might be a racist white supremacist because of the people who support him or have interviewed him has hit a media chord.

In political parlance, it's known as a guilt-by-association attack. It's one of the oldest in politics. During the nasty 1800 race, President John Adams and his supporters mercilessly attacked Thomas Jefferson's associations to paint him as a mean-spirited, low-lived fellow,

"the son of a half-breed Indian squaw, sired by a Virginia mulatto father." Not much subtly there.

A more recent and famous example was the 1988 Willie Horton ad by George H.W. Bush's supporters. It suggested then-Democratic nominee Mike Dukakis was a soft-on-crime governor because Massachusetts released a criminal on furlough who then stabbed a man and raped a woman.

Such ads can be effective .... if the candidate lobbing them doesn't own her own record of guilty associations.

Willie Horton 1988 Attack Ad

Hillary and Bill Clinton's 40 years in the public limelight has put them in touch with friends, business associates, co-workers and fund-raisers who turned out to be felons, thieves, crooked savings & loans owners, an underage sex offender and agents of foreign influence. 


In fact, more than a dozen of their associates when they were last in the White House in the 1990s or from when she ran for president in 2008 have landed in prison. Many were key figures in scandals like Whitewater, the China fund-raising investigation or straw donor criminal investigations.


Here's a Top 10 List that's a good reminder of an old adage: one should pick their battles, and their friends, carefully.

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FILE--Webster Hubbell is sworn in on Capitol Hill Dec. 1, 1995, prior to testifying before the Senate Whitewater Committee. While in prison, Hubbell kept in touch with his friends in the Clinton administration with regular telephone calls that were taped by prison officials and later turned over to Whitewater prosecutors, according to lawyers and others familiar with the investigation. (AP Photo/Ron Edmonds, File)

Webster Hubbell

Hubbell was one of Hillary Clinton's Arkansas law partners and closest family friends.   

He was a golf partner so trusted that Bill Clinton named him to be Associate Attorney General in the U.S. Justice Department in 1993. But within a year, Hubbell was forced to plead guilty to stealing at least $394,000 from his Arkansas law partners and more than a dozen clients, including the U.S. government. He went to prison. 

Hubbell was charged with new crimes a few years later related to the Whitewater investigation and pleaded guilty to two more charges in 1999, this time avoiding prison time. Today he writes crime novels.

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Hassan Nemazee arrives at federal court in New York, Thursday, March 18, 2010. Nemazee, who was once a top fundraiser for Hillary Rodham Clinton and other big-name Democrats, was indicted last year on charges that he used fake collateral to obtain more than $290 million in loans from major banks. (AP Photo/David Goldman)

Hassan Nemazee

Nemazee was a prominent Iranian-American businessman.   

He served as a Hillary Clinton's national finance director during her2008 presidential bid, bundling many donations for her campaign. He also was a foreign policy adviser and helped raise money for Bill Clinton's legal defense fund and his private foundation.

But in 2010, he pleaded guilty to stealing hundreds of millions of dollars to buy property in New York, and to donate to charities and political campaigns like Mrs. Clinton's. He was sentenced to 12 years in prison, where he remains today. He apologized in court and said he was ashamed of his conduct.

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Taiwanese businessman Johnny Chung, left, appears with President and Mrs. Clinton at a 1994 Christmas Party at the White House in Washington. Chung handed a $50,000 campaign donation to Mrs. Clinton's chief of staff Margaret Williams in 1995 on a trip to the White House with six Chinese officials to hear a presidential radio address, administration officials said Wednesday, March 5, 1997. Others in photo are Chen Shizeng, president of the Haomen Group, and He Yejun, right. (AP Photo)

Johnny Chung

He was a  businessman who admitted in the late 1990s that he funneled illegal donations to the Democratic Party and Bill Clinton's 1996 re-election campaign.

Among the things he admitted in federal court was delivering a $50,000 check to Hillary Clinton's chief of staff at the White House, despite a legal ban on fund-raising in federal buildings. 

Many of his visits to the White House before he was prosecuted were made possible by Mrs. Clinton and her staff. He became one of the central figures in the China fund-raising scandal that scarred the second term of Bill Clinton's presidency and made infamous donor visits to the Lincoln Bedroom and White House coffees.

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Norman Hsu, right, arrives with an unidentified attorney, left, and an unidentified supporter, center, at a San Mateo County Superior Court in Redwood City, Calif., Friday, Aug. 31, 2007. Hsu, a top Democratic fundraiser wanted as a fugitive in California, turned himself in Friday to face a grand theft charge. After reports surfaced this week of Hsu's fugitive status in California, Democratic presidential hopeful Sen. Hillary Rodham Clinton, D-N.Y., joined other candidates in returning thousands of dollars he raised. (AP Photo/Paul Sakuma)

Norman Hsu

He was one of Hillary Clinton's top fund-raising bundlers during her 2008 campaign and a Clinton Foundation donor until it was revealed he was a fugitive in an old California fraud case. 

His past was highlighted by Barack Obama's campaign during its efforts to defeat Hillary Clinton in the 2008 Democratic primaries. He was eventually prosecuted and sentenced to federal prison for what federal authorities said was a Ponzi scheme that bilked everyday Americans of millions of dollars.

Mrs. Clinton's campaign was forced to refund or donate to charity $850,000 he had raised for her campaign.

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Sandy Berger, former Deputy National Security Advisor, participates in a panel discussion about the Bosnian War at the Clinton Presidential Library in Little Rock, Ark., Tuesday, Oct. 1, 2013. The CIA recently posted online more than 300 declassified documents related to the conflict. (AP Photo/Danny Johnston)

Samuel "Sandy" Berger 

He was a close foreign policy adviser to Bill and Hillary Clinton and eventual White House National Security Adviser. In 2003, he pleaded guilty to trying to sneak classified

records out of the National Archives in his socks in connection with the post-Sept. 11 terrorism investigations. He hid them at a construction site in Washington D.C.

His case shocked an entire national security community that had respected Berger's work. Berger publicly apologized for what he called a lapse in judgment. "I am very sorry for what I did, and deeply apologize," he once said. He was forced to give up his law license, and died late last year.

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FILE - This July 27, 2006 arrest file photo made available by the Palm Beach Sheriff's Office, in Florida, shows Jeffrey Epstein. First came the allegations late last year that Britain?s Prince Andrew and a prominent American lawyer took part in a wealthy sex offender?s abuse of teenage girls aboard private jets, in luxury homes and on the financier?s Caribbean island. The story, part of a long-running U.S. legal fight focused on the rights of the women, gained steam when Buckingham Palace took the unusual step of issuing a carefully worded denial of the kind of salacious claims that royal officials rarely acknowledge. Defense attorney Alan Dershowitz, who represented the highly connected Epstein and was himself named in the latest court filings, then called the most outspoken of the four women a serial liar and practically dared her to prove her accounts.Instead of letting the case play out from there, the woman known as Jane Doe No. 3 hit back with a 23-page affidavit detailing dates, locations and more ab

Jeffrey Epstein

This billionaire businessman is a registered sex offender who became ensnared in a Florida sex trafficking ring investigation involving minors. He served 13 months in prison after pleading

guilty to soliciting an underage girl for prostitution. According to records reportedly submitted to authorities during plea bargain discussions, his lawyers claimed Epstein helped conceive the idea for the Clinton family foundation and flew Bill Clinton aboard his plane numerous times. 

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James McDougal talks to reporters outside the Little Rock, Ark., federal courthouse Monday, April 14, 1997, after his sentencing hearing for Whitewater offenses. McDougal received a three-year prison sentence and three years' probation, and was fined $10,000. (AP Photo/Danny Johnston)

James McDougal

He was Bill and Hillary Clinton's business partner in the Whitewater real estate venture that spawned one of the largest presidential scandals in history.  

He also operated a savings and loan that failed at a cost of $68 million to taxpayers. He was ultimately convicted on 18 counts of fraud and sent to prison, where he eventually died.

During his cooperation with federal prosecutors, he reportedly admitted arranging a meeting with then Gov. Bill Clinton to discuss a fraudulent loan that had an indirect benefit to the Whitewater real estate venture co-owned by the Clintons.

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Yah Lin ``Charlie'' Trie, a friend of President Clinton and former Little Rock, Ark., restaurant owner, leaves the federal courthouse, Monday, Nov. 1, 1999, in Little Rock. Trie was sentenced to four months' home detention and three years' probation for violating campaign finance laws. He was also fined $5,000 and ordered to perform 200 hours of community service. (AP/Photo Mike Wintroath)

Charlie Trie 

An Arkansas restauranteur who followed the Clintons to Washington, he raised significant sums of money for the Democratic Party to help Clinton get re-elected in 1996. 

 Trie also donated money to Bill and Hillary Clinton's legal defense fund. 

Trie pled guilty to violating federal election laws and outlined to prosecutors how he and others funneled foreign money into the election to benefit the Clintons. A Senate investigative report concluded that Trie had a "close relationships with the Chinese government and/or intelligence agencies."

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Marc Rich

An international financier, Rich became one of the world's most famous fugitives after he was charged in a 1980s federal fraud case that carried 300 years in prison. He escaped capture by

living in Switzerland until Bill Clinton, in one of his final acts as president in 2001, pardoned Rich. The presidential act created enormous controversy, in part because Rich's ex-wife donated large sums of money to many of the Clinton's biggest political efforts, including his presidential library and her Senate campaign. 

The pardon was so controvesial that even Democrats like former President Jimmy Carter suggested  it had been purchased by "gifts" to the Clintons and was "disgraceful."

John Solomon is Circa's chief creative officer and and an investigative reporter who has covered national politics for nearly 30 years, including many of the scandals involving the Clinton figures above.

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