McCain was one of the infamous “Keating Five” – five Congress members who tried to help the worst savings and loan of the 1980s crisis get around regulators. Between 1982 and 1987, McCain received $112,000 in political contributions from Charles Keating Jr., then chairman of the failed Lincoln Savings and Loan Association, and his associates. McCain and his family made nine trips at Keating’s expense, sometimes using Keating’s jet, according to news accounts such as the Arizona Republic. Three of the trips were made during vacations to Keating’s Bahamas retreat.

McCain knew how to pay back such generosity to his family. While in the House of Representatives, McCain was among the sponsors of a resolution to delay new regulations designed to curb risky investments by thrifts such as Lincoln.

When regulators investigated Lincoln for violating laws in 1987, Keating asked McCain and the other Congressmen to meet with regulators and plead his case. At first, McCain was “nervous” about doing so – and Keating called McCain a “wimp” for being concerned about the meetings, according to the Arizona Republic. But McCain finally agreed to do it after saying he would just ask questions about Lincoln’s treatment, not plead the thrift’s case.

So on April 2, 1987, McCain and three other senators met with Ed Gray, then chairman of the Federal Home Loan Bank Board. A week later, McCain and four senators met with William Black, then deputy director of the Federal Savings and Loan Insurance Corp., and other federal regulators. Black told the Republic that McCain was acting the “weirdest” of all the senators. “McCain was always Hamlet . . . wringing his hands about what to do,” Black said.

By the time Lincoln failed in 1989, McCain had wrung his hands long enough to distance himself from Keating. Lincoln was the most expensive failure in the scandal, as taxpayers lost more than $2 billion alone to bail out that thrift. Others such as former Sen. DeConcini continued to defend Keating until his thrift failed and the feds filed a $1.1 billion civil racketeering and fraud suit against Keating, accusing him of siphoning Lincoln’s deposits to his family and into political campaigns.

The Senate Ethics Committee investigated McCain and other Keating Five members. In 1991, the committee decided to blame most of the mess on DeConcini and former Sens. Riegle and Cranston, while only mildly rebuking McCain for showing “poor judgment” in meeting with regulators on Keating’s behalf.

McCain later admitted he showed poor judgment in his hand-wringing sessions with regulators. “It’s a wrong appearance when a group of senators appear in a meeting with a group of regulators because it conveys the impression of undue and improper influence. And it was the wrong thing to do,” McCain said. “I was judged eventually, after three years, of using, quote, poor judgment, and I agree with that assessment.”

DeConcini claims that McCain leaked to the media “sensitive information” about certain closed proceedings in the case to help make DeConcini, Riegle and Cranston take the fall. A congressional investigator, Clark B. Hall, later told the Boston Globe that McCain was one of the “principal leakers.” McCain, under oath, denied involvement with the leaks, but he was testy when a Republic reporter asked him about an alleged business relationship between Keating and McCain’s wife, calling him a liar and idiot.

Keating was convicted in state court in 1992 of fraud, racketeering, and conspiracy and received a 10-year prison sentence, serving less than five years. 

McCain’s poor judgment continues 

In 1983, McCain opposed the creation of a federal holiday honoring Martin Luther King Jr., even though Reagan signed the bill.  As late as 1994, McCain voted to cut off funding for the commission working to promote the King holiday.  

But in April 2008, as he campaigned for president, McCain admitted he showed poor judgment in opposing that holiday. "We can be slow as well to give greatness its due, a mistake I made myself long ago when I voted against a federal holiday in memory of Dr. King,” McCain said in a speech in Memphis, Tenn. “I was wrong and eventually realized that.” 

During his 1986 Senate campaign, according to the Tucson Citizen, McCain reportedly said to an audience: “Did you hear the one about the woman who is attacked on the street by a gorilla, beaten senseless, raped repeatedly and left to die? When she finally regains consciousness and tries to speak, her doctor leans over to hear her sigh contently and to feebly ask, 'Where is that marvelous ape?'” 

The alleged joke was so offensive that McCain has said he doesn’t remember saying it, even though it was reported in a newspaper. But earlier this year, McCain tried to say in jest that he “stopped beating my wife just a couple of weeks ago.”

In 1998, McCain again exercised poor judgment when he said while addressing a Republican fund-raiser: “Do you know why Chelsea Clinton is so ugly? Because Janet Reno is her father.”

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