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Hillary Clinton's Achilles Heel: 2016

02/15/2014 07:38 pm ET | Updated Apr 17, 2014

Can you solve this analogy? Which alternative best replaces the question mark?

Clinton 2008: Iraq War
Clinton 2016: ?

a. Benghazi
b. Health care
c. Wall Street
d. Syria

Answer: Option C

2014-02-15-HillaryClinton.jpg

The Iraq War upended Hillary Clinton's chances of winning the Democratic nomination for president in 2008. Wall Street, economic regulation and the risks posed by the financial industry threaten to do the same in 2016.

Clinton lost the nomination in 2008 in large part because she voted to authorize the Iraq War. As the Democratic primaries approached she tried to run away from her vote. Then Senator Barack Obama tapped into a growing sense of unease among Democrats and made the case that Clinton was a hawk who (and this seems more than a bit ironic now) could not be trusted to end Bush-era policies. He used the issue to drive a wedge between Clinton and the anti-war left, and ultimately ended up clinching the nomination.

According to the polls, Clinton is poised to be the party's nominee in 2016. And while there is not yet a candidate of Obama's stature waiting to grab the nomination from her clutches, it is like déjà vu all over again because once more she is vulnerable on an issue of concern to the left wing of her party.

This time it isn't the war, its Wall Street and financial regulation. And in a bit of historic irony, it is becoming increasingly clear that a growing number of liberals feel that Clinton is once again on the wrong side of the key issue of our time.

Recently Krystal Ball of MSNBC's The Cycle urged Clinton not to run. Ball's argument? Clinton is a shill for Wall Street and corporate interests. As Ball said,

Is someone who sat on the rabidly anti-union board of Walmart for six years the right person to restore workers' rights? Is someone who recently took $400,000 to give two speeches at Goldman Sachs the person we need to wrest control of the asylum back from the banking inmates?

Instead Ball prefers the freshman Senator from Massachusetts Elizabeth Warren who she described as a "champion of the middle class."

Ball is not the first to make this case. In September of last year Jonathan Chait wrote an article in New York magazine entitled "How to Beat Hillary Clinton." It came around the same time as his colleague Joe Hagan's cover story on Clinton's 2016 campaign and just a few weeks after Peter Beinart's piece in the Daily Beast on "The Rise of the New Left."

What all these essays have in common is they argue that Clinton is not only vulnerable to a challenge from the left, but she is especially susceptible on the issue of financial regulation, "too big to fail," and her (and her husband's) ties to big business and Wall Street.

It is no surprise that all three pieces came out just as Bill de Blasio clinched the Democratic nomination for Mayor of NYC and shortly before he coasted to a huge victory in the general election. With that win, de Blasio became the poster child -- or at least the most identifiable member -- of the progressive, economic populist wing of the party.

That both Hillary and Bill Clinton recognize this is clear by the fact that they spent New Years' Day attending de Blasio's inauguration. That may not, however, be enough to convince left-wing skeptics like Ball that Hillary Clinton can be trusted. After all, not only is she too close for comfort to big business and Wall Street, but she has yet to detail her plans to dismantle the financial industry, banking interests and those that are "too big to fail," and she is married to a man who epitomizes the moderate, centrist wing of the Democratic party.

Since leaving the White House former President Clinton has done tremendous humanitarian work via his Clinton Global Initiative, but unfortunately for his wife this may come back to haunt them both. As a scathing expose in the New York Times last summer found much of the foundation's good work was done with the help of donations from big corporations and moneyed interests. The Clinton's appear not to have any qualms about taking generous amounts of money from Wall Street big wigs to support their projects and further their ambitions. And it is just this type of uncomfortable entanglement between the Clinton's and Wall Street that raises skepticism among liberals.

It is no surprise that Ball pointed to Clinton's time on the board of Walmart and the money she has made making speeches to banking interests like Goldman Sachs. And as people delve into the workings of the Clinton foundation, we may find that this is only the tip of the iceberg.

Wall Street is to Clinton's chances in 2016 what the Iraq War was in 2008. The only question now is whether the far left can find another Obama to make this case to primary voters? While it seems unlikely at this point, it is still early enough that anything is possible.