The Men Who Wouldn’t Leave Hillary Clinton Alone

They weren’t the most popular guys around Washington. But they all had Clinton’s private email address. And boy, did they use it.

At 10:03 p.m. on June 23, 2009—five months into Hillary Clinton’s tenure as secretary of state—she received an email from Sidney Blumenthal, her longtime, and long-controversial, confidant. The subject: “Hillary: If you’re up, give me a call. Sid.”

During her early days in the Obama administration, newly released State Department emails show, Clinton received dozens of such messages on her private account from a motley, sycophantic crew of outside advisers—many of whom carried significant baggage from past controversies.

Mark Penn, who abruptly resigned in April 2008 as Clinton’s chief presidential campaign strategist, offered his opinions of Obama’s Afghanistan strategy (or lack thereof). Lanny Davis, who counted dictators among his lobbying clients, asked Clinton to raise the issue of a Washington Times reporter held by the Iranians with the Greek foreign minister.

Blumenthal emailed over and over and over again: He sent analysis on Iran, the latest gossip in the U.K., and advice on how to deal with Chinese disrespect for President Obama. At one point, Blumenthal apparently acted as a backchannel between Clinton and U.K. Prime Minister Gordon Brown.

At the same time, Clinton’s emails from 2009 illustrate a strange disconnect from the White House she served: a canceled meeting at the White House, finding out about a Cabinet gathering on the radio—and senior White House staff asking for her personal email address.

Of course, the emails, released Tuesday night by the State Department, present just one window into Clinton’s communications and interactions. (It’s the second large-scale release of Clinton’s emails, following the publication in May of hundreds of her communications on the 2012 attacks in Benghazi.) The documents only show declassified emails and exclude phone calls, meetings, and classified communications—none of which we can see.

But that imperfect window reveals some odd things. Blumenthal, in particular, comes across as the foreign policy equivalent of a late-night drunk texter. The “give me a call” email is one of many the moonlighting adviser fired off in 2009. Blumenthal sent that message in June, as Clinton was considering whether to bring him onto her State Department staff, an idea the White House eventually nixed. But that didn’t stop the journalist and longtime Clinton loyalist from chiming in on myriad issues and personalities on which he purported to have insider knowledge.

Blumenthal gave Clinton advice on what she ought to say on U.S. policy toward Iran. He passed her a laudatory opinion piece in Foreign Policy magazine, noting there “will likely soon be other analyses in the same vein as I am led to understand,” without specifying his source.

Blumenthal also pressed Clinton on how she should deal with German Chancellor Angela Merkel, Italian Prime Minister Silvio Berlusconi, and Irish politicians. And he dished gossipy tidbits he was picking up through his personal contacts in the British government.

In a May email, titled “from rome... Sid,” Blumenthal wrote, “I also should relate to you when I return information about [U.K. Prime Minister Gordon] Brown government re foreign ministry.”

In another email, Blumenthal updated Clinton on the U.K. results for the 2009 European Parliament election. In another, he wrote that “it would seem proper and decent for the President to call Berlusconi to express his concern about his health and wish him a speedy recovery.”

Blumenthal apparently was eager to brag to strangers about how essential he was to the secretary of state. On June 5, 2009, State Department spokesman P.J. Crowley wrote Clinton to say Blumenthal had “outed himself” about coming to work at the department during a conversation with an Associated Press reporter, “mentioning it without realizing he was talking to someone who actually covers our building.”

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Mark Penn, Clinton’s widely disliked 2008 campaign strategist, also offered his two cents on foreign policy from time to time.

“I can’t tell if anyone is listening to Obama at [the United Nations] but the lack of clear Afghanistan policy is unwinding the coalition and threatens to cause a massive deer in headlights problem for administration if not resolved soon,” he wrote in an email on Sept. 24, 2009.

In October of that year, Penn sent another email, this time criticizing Obama’s action toward the Taliban, calling it “politically…quite dangerous.”

While Penn has managed a number of overseas political campaigns, his experience in matters of international security is thin. Yet he continued to opine.

“Obama maintained througout [sic] the campaign and the start of his presidency that this is the one to fight and backing down here makes him and the administration vulnerable to losing moderate support and seeming weak and indecisive,” he wrote Clinton. “A single terrorist incident would be blamed on the admin. failing to do the job right.”

Then there’s Lanny Davis, the Clinton ally for decades. He knew her at Yale Law and was the chief counsel who dealt with Whitewater and other Clinton tribulations in the 1990s.

In one email exchange, Davis reached out to Hillary on behalf of John Solomon, then editor of the Washington Times, who was trying to get help for a reporter being held by the Iranians. Davis noted before the request that Solomon had been “always fair to us as AP reporter and later Wash Post reporter.”

“He says Greeks have good relations and he believes they are trying to help. He believes you are meeting with Greek Foreign Minister tomorrow and hopes you can raise the issue with him - he may already know something about it,” Davis wrote. “Any information he knows would help family. Hope you can do this - And hope your elbow is better.”

Clinton, in turn, sent an email to her State Department aide Jake Sullivan: “Would you pls give Lanny a report and do you know who is keeping Solomon informed?”

Meanwhile, the newly released communications also reveal a strange detachment between Clinton and the White House.

In June 2009, Clinton reached out to top aides about a supposed meeting at the White House. “I heard on the radio that there is a Cabinet mtg this am,” she emailed. “Is there? Can I go? If not, who are we sending?” Turns out there was no full Cabinet meeting.

Days later, Clinton arrived at the White House and was told her meeting was canceled, the second time this had occurred.

“I arrived for the 10:15 mtg and was told there was no mtg,” Clinton wrote in an exasperated email to senior aides. “Matt said they had ‘released’ the time. This is the second time this has happened. What’s up???”

It wasn’t the only communication difficulty between the White House and Clinton. While many of Clinton’s outside advisers had her private email, many of the top officials within the administration weren’t able to reach her on it.

In June 2009, an aide emailed Clinton to say that White House aide David Axelrod was looking for her private address. In September, her chief of staff raised the same issue with Clinton regarding White House chief of staff Rahm Emanuel.

“Axelrod wants your email - remind me to discuss with you if i forget,” Cheryl Mills wrote in the subject line of an email to Clinton.

The emails indicate that famed diplomat Richard Holbrooke, the administration’s point man on Afghanistan and Pakistan, did not have the same access to Clinton enjoyed by outside advisers like Blumenthal. Despite being the most prominent State Department official besides Clinton, it appears that Huma Abedin, Clinton’s right-hand woman, was his main point of contact when trying to reach the secretary.

“Does [Holbrooke] have an email address?” Clinton asked an aide in November 2009, 11 months after they both joined the administration.

When Clinton broke her elbow in the summer of 2009, both John Podesta and Colin Powell emailed her jokes about Holbrooke tripping her.

Powell, former secretary of state and chairman of the Joint Chiefs of Staff, wrote: “Hillary, Is it true that Holbrooke tripped you? Just kidding. Get better fast, we need you running around. Good being with you the other evening.”

The Clintons even appeared to be somewhat reliant on gatekeepers when dealing with each other.

“If u r still up, wjc landed in brazil for refuel,” Abedin wrote Clinton in June 2009. “He should be on ground for an hour or so. Call dougs cell.”

“I tried Doug twice but it went right to voice mail,” Hillary responded at the end of the email chain. (The “Doug” in question is likely then-Bill Clinton aide Doug Band.)

The former president didn’t even tell his wife when he became the U.N. special envoy to Haiti, instead conveying the news via Band. “Wjc said he was going to call hrc but hasn’t had time,” Band wrote to Abedin and Mills after the news of the appointment had already gone public.

There are also several emails arguing over the substance of the U.S. policy in Afghanistan, often filled with biting criticism and assertions the policy was, as one adviser wrote in a September 24, 2009, email, “unwinding.”

Longtime Clinton advisers addressed efforts to get around the flailing government of then-Afghanistan President Hamid Karzai—by working with Pakistan or striking some kind of deal with the Taliban.

The implication was they didn’t trust the then newly re-elected president to solve Afghanistan’s intractable problems.

And even Clinton had trouble sorting out what the U.S. was supposed to say to Karzai. In a December 28, 2009, email from Clinton titled “Karzai call?” the secretary of state asks: “What, if anything, was decided about whether I should call him? The email traffic I read has Holbrooke saying ‘yes’ and Frank R disagreeing. Can you update pls.”

By then Obama had delivered a speech at West Point, New York, outlining the U.S. withdrawal plan from Afghanistan. In the email chain, no one has an answer for Clinton on whether she should call the U.S.-backed Karzai.

—with additional reporting by Jackie Kucinich, Nancy A. Youssef, Shane Harris, Noah Shachtman, Will Rahn, and Betsy Woodruff