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On no stormy sea has Penn been more of an anchor for Clinton than on Iraq, so far the defining issue of the 2008 election. "I don't think there's any gap in their thinking," said Douglas Schoen, Penn's former business partner.
As her position has evolved, from initial support for President Bush to fierce criticism of the war's management, Clinton has sought a careful balance, one that maintains her image of strength on national security while not antagonizing the staunchly antiwar elements of her party. Asked repeatedly by antiwar Democrats to apologize for her original support for the war, Clinton has refused. Penn has been among her strongest backers on that score, according to Clinton's advisers, agreeing that to apologize would be disastrous both politically and on the merits.
It was Penn, famously rumpled and awkward in public, who picked a fight at a Harvard forum this year when he disrupted a mild exchange between consultants to accuse Sen. Barack Obama (D-Ill.) of equivocating on Iraq. Penn's outburst seemed designed to reach antiwar Democrats by shifting attention away from Clinton's initial support for the war by arguing that she and her main rival have similar approaches to ending it.
"When they got to the Senate, Senator Obama's votes were exactly the same" as Clinton's, Penn told the panel. "So let's not try to create false differences when we both agree it's time to de-escalate, when we both agree it's time to end this war, and let's be clear that Senator Clinton thinks that, Senator Obama thinks that."
His remarks enraged David Axelrod, a senior Obama adviser, who called the characterization dishonest.
Penn plays down his role in advising Clinton on Iraq. "I'm definitely not a national security adviser," he said in an interview in his office. "I think I understand the issue. But I leave that to the policy advisers who are very close to her."
To Penn, 'Strength Is Critical'
In their $5 million Georgetown mansion, Penn and his wife, Nancy Jacobson, a former staff member for Sen. Evan Bayh (D-Ind.) who is now a fundraiser with the Clinton campaign, run something of a salon for like-minded friends. They recently threw a book party for Jeffrey Goldberg, the New Yorker writer, to celebrate the release of his memoir on Israel. On another occasion, they hosted David Brooks, the conservative New York Times columnist, for a dinner party and political discussion.
Penn has deep roots in the national security wing of the Democratic Party, along with other centrist Democrats -- some of them Jewish and pro-Israel, like Penn -- who saw the merits of invading Iraq before the war began.
"Penn has always believed that strength is critical for running the country, and that people want to have a president who's going to be willing to defend the country -- that's the number one criteria," said Al From, the chief executive of the Democratic Leadership Council, who considers Penn a friend.
Penn gained his foreign policy expertise working on numerous campaigns overseas, especially in Israel. In 1981, he and business partner Doug Schoen helped reelect Menachem Begin, one of the most right-wing prime ministers in the country's history, and emerged with a new outlook on the Middle East. "We got a chance to experience firsthand the perils and possibilities that the state of Israel presents," Schoen said in an interview.
In a pivotal moment, the pollsters watched as Begin launched airstrikes against a developing Iraqi nuclear facility, Osirak, in the middle of the campaign. "In the end, bombing the Osirak reactor became a metaphor for the type of man that Begin was and the steps he was willing to take to safeguard Israel's security," Schoen wrote in his autobiography, "The Power of the Vote."
Ever since, Penn has been a prominent advocate of conveying strength in foreign policy. As recently as the 2004 presidential contest, Penn argued that Democrats would lose if they failed to close the "security gap." His client list includes prominent backers of the Iraq war, particularly Lieberman, whose presidential campaign Penn helped run in 2004, and British Prime Minister Tony Blair, whose campaign he advised when Blair won a historic third term in 2005.