Penn had served as Clinton's chief strategist during her unsuccessful 2008 presidential campaign, an effort that was riven by internal infighting, including disagreements over Penn's advice. Among his most persistent advice was for Clinton to avoid being seen as weak or emotional because voters might have trouble accepting those traits from a female president.
Penn's comments on the Benghazi hearing came as much of Clinton's staff was internally crowing about her appearance. The newly released e-mails show that Clinton's inbox was filled with praise from friends and employees about the outing. ("She was incredible. So, what's the right word? Presidential," wrote Tom Healy, chairman of the Fulbright Board.)
The State Department released 7,800 pages of Clinton's e-mails on Monday, part of its months-long effort to make public 55,000 pages of e-mails she sent and received in office.
At the time, the internal reaction to Penn's note was not positive. Clinton aide Philipe Reines forwarded the note, calling it the first "discordant note--just to keep it real" and then followed up with a note saying that he's never had a problem with Penn but "Give. Me. A. Break. You did not look rattled. You looked real. There's a difference. A big one."
Deputy Secretary of State Jake Sullivan then replied to Clinton and her chief of staff: "My problem with Mark's analysis is that it repeats the same flawed assumption that underpinned his 2008 advice; namely, that being yourself is risky."
Clinton herself then jumped into the conversation, suggesting she remained critical of Penn's 2008 advice, even five years later. To Sullivan's assessment, she responded: "BINGO!!"
Still, history may have borne out some truth to Penn's point. The climactic moment of that hearing was Clinton's retort to Sen. Ron Johnson (R-Wis.). "With all due respect, the fact is we had four dead Americans," Clinton told Johnson. "Was it because of a protest, or was it because of guys out for a walk one night who decided they'd go kill some Americans? What difference at this point does it make? It is our job to figure out what happened and to do everything we can to prevent it from ever happening again, senator."
Clinton's "what difference at this point does it make?" quote, seen by her team as a powerful take-down of the freshman senator, has since become a rallying cry for her conservative critics.
This item has been updated to reflect Clinton's response to Penn.