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The 5 topics that could hurt Hillary Clinton in tonight's debate

Democratic presidential candidate Hillary Clinton prepares to leave after speaking to union members gathered in front of the Trump International Hotel & Tower Las Vegas.
Democratic presidential candidate Hillary Clinton prepares to leave after speaking to union members gathered in front of the Trump International Hotel & Tower Las Vegas.
Joe Raedle/Getty Images

Many in the media decided Hillary Clinton was likely to lose Tuesday's first Democratic presidential debate long before CNN went live from Las Vegas.

Bloomberg's Mark Halperin best encapsulated this establishment view this weekend when he said that if Clinton makes a single mistake, it will be the "only story" out of the debate. Setting aside the self-fulfilling nature of that prophecy, it's true that any frontrunner has the most to lose in a political debate. That's why the frontrunners tend to want to limit the number and scope of debates, and challengers generally want as many chances to debate as possible.

Clinton has the most to lose in Tuesday night's debate because she's in first place — and by a wide margin. Bernie Sanders will get a boost in legitimacy just by being onstage with her, and Vice President Joe Biden can use any flaw, real or perceived, to springboard into the race. The other three candidates onstage — Martin O'Malley, Lincoln Chafee, and Jim Webb — appear to stand no chance of winning the nomination, but they could certainly damage Clinton by pointing out where she differs from a Democratic base that is increasingly comfortable defining itself as "liberal." In 2008, her debate-night stumble over the question of whether unauthorized immigrants should be permitted to have driver's licenses proved to be one of the turning points in the Democratic primary.

None of that means Clinton will lose Tuesday night. Despite the driver's license question, she proved to be a very talented debater in 2008. It's a strength that Barack Obama's team readily acknowledged and one that Clinton's rivals should not take lightly. With a strong performance, she could start to put the field in her rearview mirror and keep Biden on the sidelines.

But there are more risks for her than for any other candidate. Here are five of them.

1) The influence of money on politics and policy

Clinton has tried to blunt criticism that she's too close to her donors on Wall Street and in corporate America by promising to appoint Supreme Court justices who would reverse Citizens United and by calling for a constitutional amendment banning such soft money from campaigns. But this is still a huge vulnerability for her.

Sanders, her closest competitor, doesn't have a PAC and rails constantly about the evils of campaign donors influencing American policy. He's got credibility on the issue, and she's left to argue that she would regulate her friends. Plus, there aren't any major industries she's taking money from that are donating more to other candidates. I met a Sanders voter in Iowa who was critical of Clinton for taking money from employees of private prison corporations.

The issue goes beyond the cash her campaign takes from the 1 percent. The Clinton Foundation, where Hillary Clinton worked between her time at the State Department and her presidential run, is awash in money from major corporations that have big business interests inside and outside the US. Vox counted 181 Clinton Foundation donors that lobbied the State Department while Hillary Clinton was secretary, and she and Bill Clinton earned speaking fees from several of them after she left the government.

There's no evidence that the Clintons did favors for donors — despite a lot of effort to prove that they did — but the sprawling web of Clintonworld donors makes many Democrats uncomfortable, and none of the other candidates have such entanglements.

2) The email scandal that continues to haunt Clinton

For some time, there have been two Clinton campaigns. The first has been rolling out her platform, raising money, and building an organization on the ground. The second has been responding to the slow burn of an email scandal that still dominates coverage of Clinton in the media.

She's likely to be asked a lot of questions about whether she compromised national security by putting her work email on a private server and why she didn't just come clean about it in the beginning. What she and her team have found over time is that there are no good answers.

She's been handed a few gifts of late: House Majority Leader Kevin McCarthy acknowledged the political nature of the House Benghazi Committee's investigation into Clinton, and one of the panel's staffers says he was fired for not targeting her aggressively enough (a charge the committee disputes).

But this has been the singular focus of the media, and Clinton has yet to produce a convincing answer on why she set up her email system the way she did.

3) Clinton's hawkishness doesn't sit well with dovish Democrats

Thirteen years ago this week, Clinton voted to give President George W. Bush the authority to invade Iraq, and the debacle there is still the biggest strike against her among many Democratic primary voters. Obama used his prewar warning about Iraq as a bludgeon against Clinton in 2008, and Sanders has been rallying dovish Democrats by talking about his opposition to the war as part of his stump speech.

Clinton acknowledged making a mistake, but she's very open to the charge that she's still too hawkish for Democratic primary voters. Webb, who opposed the Iraq War, has been critical of the administration's decision to strike Libya in 2011. Clinton stitched together the international coalition that paved the way for the attack. The policy was successful in driving Muammar Qaddafi from power — he was ultimately executed by the side of a road — but the country has descended into chaos.

In December, Jacob Heilbrunn argued in the New York Times that it was Webb, a former Marine and Navy secretary under Ronald Reagan, who posed the greatest threat to Clinton's candidacy because "divisions over foreign affairs could be a lot harder to paper over" than differences on domestic policy. And Webb has the credibility of a veteran who wore his son's combat boots when he campaigned for the Senate in 2006.

Clinton's challenge will be to explain why her "smart power" approach to American foreign policy — which includes using the military — is the right one, even if many Democrats think she is too quick to embrace force.

4) The debate about debates

It's likely that the moderators will try to get Clinton to agree to more than the six debates that have been scheduled by the Democratic National Committee.

Her rivals want more debates, and DNC Chair Debbie Wasserman Schultz (my former boss and a longtime Clinton ally) has been harshly criticized by other candidates — and even two of the committee's vice chairs — for holding firm on the number. One vice chair, Rep. Tulsi Gabbard, says she was told by a DNC official that she shouldn't attend the Las Vegas debate because she has been a vociferous supporter of increasing the number of debates. At a party meeting in Minneapolis in August, O'Malley accused the DNC — and Wasserman Schultz — of designing a debate schedule "rigged" to help Clinton win.

Clinton probably doesn't want a string of extra chances for the other Democrats to upset her campaign, but arguing to stick to the schedule reinforces the idea that she doesn't want an open competition.

5) Letting her aides play by a different set of rules

One of the big knocks on Clinton from Republicans and Democrats alike is that she plays by her own set of rules. The email scandal is exhibit A. But there's a new line of attack that Clinton's likely to have to answer for: letting her aides work for State and outside entities at the same time.

The Washington Post reported Monday that Clinton's chief of staff, Cheryl Mills, had a special temporary employment status for her first four months at State so that she could continue negotiating a deal to put a campus of New York University in Abu Dhabi. That follows on the story that Clinton's deputy chief of staff, Huma Abedin, was allowed to invert her relationship with State to that of a contractor while she worked on the outside for Teneo, an international consulting firm.

Clinton's critics say these arrangements presented potential conflicts of interest for Mills and Abedin, though they both strenuously deny that they did anything improper. Clinton's Republican adversaries say she plays by a different set of rules than everyone else, an umbrella argument that covers her top aides' ability to draw outside income at State and her exclusive use of a private email server.

VIDEO: Republicans (try to) describe Hillary Clinton in two words