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Until then, every lesson the Army had taught him said to avoid the press, that nothing good would come of speaking to reporters.
A month into the job, coalition forces dropped the bomb that killed Abu Musab al-Zarqawi, then one of the most-wanted insurgents in Jordan and Iraq. Zarqawi had claimed responsibility for several suicide bombings and hostage beheadings and had trained militant Islamists in Afghanistan.
Thanks to his long military background — his career now spans 32 years — Caldwell knew exactly whom to call to get the story straight for the press. His first call was to Lt. Gen. Stanley McChrystal, Commander, Joint Special Operations Command, who had been one of Caldwell's classmates at West Point. He also called the first responders, who had pulled the mortally wounded Zarqawi out of the rubble of his safehouse, and the pilot who had dropped the bomb.
"They understood they could share a lot of classified stuff with me, and I was able to sort through probably what could or couldn't be said," Caldwell says. "Just give me the story from A to Z, and I think I'm probably smart enough to figure out what's special tactic and technique we don't want to expose, and what the American people and the rest of the world have the right to know."
Still, he explains, being thrown into the role of spokesman left him plenty of room to make mistakes.
"You mean, like, was there a time when I said something in a news conference that was on the front page, above the fold, of The New York Times: 'General disheartened by actions in Iraq'? Hmm, let me think," he says and then laughs. "And then did I get a personal note from then Secretary of Defense Don Rumsfeld about it? Ah, yeah, I think I did, as a matter of fact."
What did the letter say? Caldwell expertly sidesteps the question. This is what makes him an ideal teacher of "strategic communication" for his war-college officers — he doesn't stray far from the story he wants told. He knows the job is about releasing information that will increase the public's understanding of the Army's point of view. Telling engaging anecdotes and uncorking insights that offer the faint suggestion of privileged information — well, that doesn't hurt.
As spokesman, Caldwell did release a lot of previously classified information — with Casey's permission.
"That was huge," Caldwell says. "Before me, they had not been doing that. He [Casey] had given me that authority. It allowed me to turn things. And then he finally assigned me intel officers, two intelligence officers that were assigned to my organization, whose sole job was to declassify stuff. I'd throw them a whole bunch of papers after a briefing and say, 'I need as much of this declassified as rapidly as you can.' And so their job became going back to the original source and getting as much declassified as they could."
Once he landed at Fort Leavenworth, Caldwell says, he made it his mission to teach officers at the college the lessons he'd learned as a spokesman for the war. "I walk in here — and I've had a life-altering event at this point now. Never, ever, had anything impacted me more than having to stand up there — and how ill-prepared I was, how uncomfortable I was the first couple months. And I thought, I can't allow other officers to continue to grow up in our army that ill-prepared."