Steve Clemons, writing for The Guardian in 2009, hinted that Ted Kennedy may have had the idea that his niece, Caroline Kennedy, would not only succeed him as the family flag-bearer, but would be in a position to succeed Barack Obama in 2016. The same thought occurred to me recently during Michelle Obama’s visit to Japan, where she toured a Buddhist temple along with Ambassador Kennedy. In the context of the latest Hillary snafu—this time over Clinton’s use of a private e-mail server—the thought of voting for Caroline as the first woman to be President of the United States was a refreshing daydream.

Caroline endorsed Barack Obama in 2008 (as did her uncle Ted). The Clintons were not happy about it. Perhaps feeling that there were fences that needed mending, last year (April 2014) Caroline said that she would support Hillary if she decides to run in 2016. Well, so much for daydreaming, but I wish she hadn’t said that. Meanwhile, the extended Kennedy clan is apparently split between endorsing Hillary and urging Elizabeth Warren to run. Warren has been blunt in stating that she does not want to run: “No. I am not running and I am not going to run.” Warren’s ability to speak clearly is why we love her, but obviously our affection is insufficient motivation for Liz to jump into the presidential fray. Well, at least not before Hillary makes her Big Announcement.

I would like to be enthusiastic about Hillary, but I can’t help thinking that she is the dream Democratic candidate of the Republican Party. I am lately bewildered by Hillary’s inability to master the use of email. There are certain skills that the nation’s chief executive ought to have, and email is not new-fangled (its beginnings pre-date the Internet and general use of email has been around at least since 1995, when Bill was president). Hillary has been less than adroit in her response to the email controversy. At first, she delayed responding to the report in the New York Times that as Secretary of State she used a personal email account rather than a government address. Finally breaking her silence at a press conference at the United Nations, she brought up the email issue almost as an afterthought (after addressing the UN efforts toward gender equality and the letter sent by Republican Senators to undermine the ongoing negotiations regarding Iran’s nuclear program). After thinking about it for more than a week, the best she could come up with was part lame excuse (“I thought it would be easier to carry just one device”) and part political tone-deafness (“We went through a thorough process to identify all of my work-related emails and deliver them to the State Department. At the end, I chose not to keep my private personal emails”).

The campaign trail appears headed toward a tangled thicket of Benghazi, border security, email and Obamacare. Is it any wonder that I daydream about a leader to show us the way back to the New Frontier?

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