Twenty years ago Michael Chertoff was near the top of the Clintons’ enemy list. He was the lead Republican counsel on the Senate Whitewater Committee, one of the first of many Congressional investigations into Hillary Clinton.
Clinton later cast the only vote in the Senate against him when he was nominated in 2001 to head the Justice Department’s criminal division. She was also the lone no vote against Chertoff in 2003 when he was nominated to the U.S. Court of Appeals for the third circuit.
All of this though was before the Republican Party nominated Donald Trump as its presidential candidate. This has shaken the party of Reagan. Chertoff, a life long Republican, will now be voting for the Democrat in November.
Over the weekend, Chertoff — the former secretary of Homeland Security — told me his decision came down to national security. “I realized we spent a huge amount of time in the ’90s on issues that were much less important than what was brewing in terms of terrorism,” he said. For Chertoff, Clinton “has good judgment and a strategic vision how to deal with the threats that face us.”
Whitewater has not come up much in this election season. But it was the Benghazi of the 1990s. Just as the Benghazi investigation begat a Congressional probe into Clinton’s e-mail server, the Whitewater investigation led Congress to President Bill Clinton’s affair with Monica Lewinsky. So it’s significant that an investigator from that era is now in Hillary Clinton’s corner.
“People can go back decades and perhaps criticize some of the judgments that were made,” Chertoff said. “That is very, very insignificant compared to the fundamental issue of how to protect the country.”
Just as Chertoff does not think Clinton’s dodgy friendships from her Arkansas days disqualify her from the presidency, he says the same thing about Clinton’s use of a private e-mail system. It was a mistake, he said, but “she did not intentionally endanger national security.”
Trump, on the other hand, lacks the temperament and knowledge base to be president. Chertoff has made his views on the Republican nominee known before. Last month, he was one of the 50 former senior Republican national security officials to sign a letter warning Trump would be a dangerous commander-in-chief. But many of those former officials have not crossed over to publicly endorse Clinton.
Chertoff says he made the decision to go public for Clinton after watching the debate last week. “Trump’s sense of loyalties are misplaced,” he said. “Some of our NATO allies sent troops overseas, at the same time he is defending Russia and trying to dismiss what is widely acknowledged to be Russian intrusions into the databases of our political parties and political figures.” Chertoff said this amounted to “making enemies of your friends and cozying up to your adversaries.”
For Chertoff it’s also a question of Trump’s impulse control. “This issue came up at the debate about Miss Universe,” he said. “Not only did he seem at the debate to lose his temper, but to get up at 3:30 a.m. and reach for your smartphone is to me a hysterical reaction. If you’re president, the button you reach for is not the Twitter button; it’s the nuclear button.”
Chertoff’s relationship with Clinton began to heal after he was nominated to be the second secretary of Homeland Security, in 2005. Clinton voted for him that time. Chertoff said that while he was secretary, he found Clinton to be “clear eyed and tough on national security issues.”
Chertoff said he expects Clinton will be different from President Barack Obama when it comes to Middle East policy. “There are things Obama did that I disagree with, not to have a no-fly zone and a safe zone in Syria, for example,” Chertoff said. “My understanding from having talked to her and seeing what she has said publicly is that she would have been tougher on that.”
Chertoff’s decision to endorse Clinton puts him on the opposite side of one of his earliest political patrons. In 1983, Chertoff was hired as a prosecutor by then-U.S. Attorney Rudolph Giuliani. Together they waged a devastating legal war against the five mafia families of New York. The success of those prosecutions laid the groundwork for Giuliani’s successful campaign to become mayor of New York.
Today Giuliani is one of Trump’s closest advisers. Chertoff told me he has not talked to Giuliani about Trump. “People make their own decisions,” he said. “I can’t get into someone else’s head.”
Lake is a Bloomberg View columnist writing about politics and foreign affairs.