For the most part he's worked as a lawyer and/or prosecutor his entire adult life. In the late 70s he served as the basis for a character in a Scott Turow novel and in the 80s was chosen by Rudy Giuliani himself to help prosecute a case against a huge mafia crime syndicate. Read more about both of these facts at NewYorker.com.
Chertoff spent time working for various law firms including one that helped go after the Clintons in the Whitewater fun. To this day, Hillary is not a fan. Back in 2003 when he was up for a judgeship of the U.S. Court of Appeals for the 3rd Circuit, in New Jersey, Hillary was the only Senator to vote against him and is now expected to vote against him again. The funny thing is that back in 2002, he was offered the SEC top spot, he turned it down saying, according to a November 15, 2002 CFO.com article that:
...he's "happy" to remain as head of the Justice Department's criminal division.
Lessee, what else did I dig up? Elaine Cassel wrote an essay for Counterpunch.org back on June 11, 2003 that explained in very pointed terms how Chertoff shoved himself into a subordinate's case to stop a suspected terrorist on trial from having access to another suspected terrorist who was currently in federal custody outside of the country on the grounds that it could pose a danger to national security. A lot of people don't know about the 6th Amendment--it says:
In all criminal prosecutions, the accused shall enjoy the right to a speedy and public trial, by an impartial jury of the State and district wherein the crime shall have been committed, which district shall have been previously ascertained by law, and to be informed of the nature and cause of the accusation; to be confronted with the witnesses against him; to have compulsory process for obtaining witnesses in his favor, and to have the Assistance of Counsel for his defence.
Of course, there's more. While AllianceForJustice.org says Chertoff:
received a "well qualified" rating from the American Bar Association
Nevertheless, his behavior in the Whitewater investigation and his current role in the War Against Terrorism raise questions about his partisanship and his belief in the civil liberties of all people.
The piece I found on Chertoff that seemed to be the most concise and well-composed voice against Chertoff's getting the Homeland Security gig is this one at Slate.com written by Fred Kaplan. He talks about Chertoff's questionable-ness, acknowledging that while he does have a lot of experience prosecuting cases, he was only a judge for 18 months and:
he has never run a large organization, managed a big budget, or dealt with larger issues of national security, transportation, infrastructure, or technology. There is also reason to wonder if Chertoff might wind up less a dispassionate analyst than a partisan cheerleader. In the mid-'90s, he worked as the Republicans' counsel on Al D'Amato's Senate Whitewater Committee. He made public appearances on behalf of Sen. Robert Dole's presidential bid, attacking Clinton on moral charges that the committee had raised (but not proved). And even in those realms of homeland security where Chertoff has clear expertise, his position on key issues is unclear or contradictory.
So, while it looks like we won't have a very scary guy as HS head, we will have a guy who is scary...in a different way. I mean, just look at that Chertoff-guy's face... he's like Skelator's ugly little brother...
OH and I also found one guy who noticed that "Chertoff" as a word is very similar to the Russian word for "devil."
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