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The 3 biggest problems facing Hillary Clinton’s presidential candidacy

Two massive stories focused on the world of the Clintons -- Hillary, Bill and Chelsea -- came out on Sunday. The first, in New York magazine, was a generally friendly treatment that made clear that Hillary Clinton is running for president in 2016 -- even if she doesn't know it yet. The second, in the New Republic, was a far tougher piece profiling Doug Band, Bill Clinton's long-time consigliere.

Scott Olson/Getty Images - Former President Bill Clinton, his wife, former secretary of state Hillary Clinton, left, and their daughter Chelsea Clinton speak to guests at the Clinton Global Initiative (CGI) on June 14 in Chicago.

Having read both stories, it's clear that the Clinton's political/personal/policy worlds have many strengths but also several critical weaknesses that could dog Hillary is she decides to run for president.

Here's three.

1. The too-extended Clinton inner(ish) circle.  The seeming conflict of interest that TNR's Alec MacGillis details in his Band profile are the most obvious of a deeper issue that has reared its head in recent months.  From Huma Abedin's marriage to political pariah Anthony Weiner to Terry McAuliffe's controversy regarding a green-car company, this summer has shown how vulnerable the Clintons are to problems that people in their universe run into. Any story that has ties to the Clintons will become a major story. This is an everything-old-is-new-again problem for the Clintons who, throughout their long stretch of time in the national spotlight, have prized loyalty to them above all else.  And, it's gotten them into trouble. (Think Susan and Jim McDougal. Or Tony Rodham. Or Denise and Marc Rich.)

2. Caution. We've taken note before of the remarkable caution-bordering-on-paranoia that Clintonworld has adopted when it comes to Hillary's run-up to the 2016 campaign. That timidity is most obvious in her guarded response -- a background quote from an adviser(!) -- on Syria but is also evident in the New York magazine piece when it comes to "Ready for Hillary", a super PAC dedicated to putting together the foundation for a 2016 GOP bid for her. Here's what Joe Hagan wrote about the PAC: "Launched early this year, it has appeared to many observers to be an informal satellite of Hillary’s larger designs for the White House, but her aides say it’s a rogue operation of questionable benefit. 'There is nothing they are doing that couldn’t have waited a year,' says one. 'Not a single [expletive] thing.'” Obviously, given the amount of media attention Hillary draws when she does anything, some level of caution is absolutely warranted. But remember that she lost the 2008 Democratic presidential nomination at least in part due to caution -- from her vote for the use of force resolution in Iraq to her unwillingness to fully embrace the historic nature -- first woman president? -- of her candidacy.

3. Bill. The former president is both Hillary's greatest potential political asset and her greatest potential political liability -- all rolled into one.

Former President Bill Clinton speaks about health care at the Clinton Presidential Center in Little Rock, Ark., Wednesday, Sept. 4, 2013. (AP Photo/Danny Johnston) Former President Bill Clinton speaks about health care at the Clinton Presidential Center in Little Rock, Ark., Wednesday, Sept. 4, 2013. (AP Photo/Danny Johnston)

MacGillis' story details how Bill Clinton took a laissez-faire attitude toward Band's increasingly blatant use of his position as the consigliere to the former president to make money for himself.

It also details Clinton's well-known -- in political insider circles at least -- post-presidential jet-setting with the likes of billionaires Ron Burkle and Steve Bing.

And then there is the history of Bill Clinton as surrogate-in-chief for his wife.  It's hard to argue that Bill Clinton helped his wife's 2008 candidacy more than he hurt it -- thanks to dismissive comments about Barack Obama's victory in South Carolina and his referring to Obama's opposition to the Iraq war a "fairy tale".

Bill Clinton has always been someone of tremendous abilities and tremendous flaws -- both in his own political career and in support of his wife's. That won't change if Hillary runs in 2016.

Chris Cillizza writes “The Fix,” a politics blog for the Washington Post. He also covers the White House.



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Chris Cillizza · September 23, 2013

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