In the two weeks of Hillary Clinton’s re-entry in pop and political culture with her book tour, she has demonstrated a remarkable inability to connect with people, to communicate effectively, and to even comprehend the damage she’s doing to herself. Any other politician with this kind of fortnight would find it fortunate to be called a mediocrity. To make this point, let’s start with the contrarian view. Bloomberg’s Jonathan Bernstein wants to remind everyone of “Hillary’s Mad [Political] Skillz” today, but doesn’t exactly make a compelling case:

Klein sums up Hillary Clinton this way: “Her political career has involved winning a Senate seat in New York over a weak Republican opponent in a year that Al Gore carried the state by 25 points — and squandering a massive lead against candidate Barack Obama in the 2008 Democratic nomination battle.”

Well, sort of. She also managed to win a very valuable open Senate nomination despite not actually being from the state; she built an impressive lead in the 2008 nomination battle, crushing several candidates, only to come up just barely short; and she has now built what appears to be an unprecedented lead — outside of incumbent presidents and vice-presidents — for the presidential nomination.

In the words of Jules Winnfield, allow me to retort. Hillary rode a wave of public sympathy over the Lewinsky affair, the resurgent popularity of her husband, and her celebrity to carpetbag into what was otherwise a dull Senate primary in New York, along with the then-invincible Clinton machine, to win a US Senate seat in deep-blue New York. She built an impressive lead in the 2008 nomination with the same Clinton machine against a field of non-entities, only to blow the lead and the nomination to a one-term Senate backbencher who had an even less impressive resumé than she did. She has a massive lead now in a race of one, because everyone else is smart enough to lay low until 2015.

Philip Klein comes much closer to the mark:

After previously trying to justify her six-figure speaking fees by claiming she and Bill Clinton were “dead broke” when leaving the White House, she’s come under fire for stating that she wasn’t that “well-off.” This has led to a spate of stories about whether the Clintons’ enormous wealth would weigh on her presidential ambitions in a nation with growing populist sentiment. But the deeper takeaway from her recent dustups isn’t her wealth, but that she’s an overrated politician. …

My operating assumption is that by the time the campaign rolls around, Hillary will find a way to answer questions about her wealth. It’ll probably go something like: “Bill and I have been fortunate enough to have a lot of opportunities, but I recognize that a lot of poor and middle class Americans aren’t so lucky, which is why I’m fighting for [insert redistributionist policy here].”

But all sorts of questions are going to come up over the course of a long campaign — some easily anticipated, others surprising. Her recent tone-deaf answers on questions about wealth speak to the fact that she’s a lot more politically clumsy than people assume.

My operating assumption is that she would have come up with that answer by … oh, the day after her “dead broke” gaffe with Diane Swayer. Instead, she’s still trying to pretend that she’s had it tough her whole life, right up to almost yesterday, apparently in the belief that Americans will identify with her “struggle.” That’s why she tried telling the Guardian that her wealth — unlike others — was made by “dint of hard work.” In my column for The Week, I explore that claim a little, and show why it’s poison for Democrats in the midterms:

“The dint of hard work,” as Clinton describes it, consisted of record-breaking bonuses for three (probably ghostwritten) memoirs (two for her, one for Bill), plus massive fees for delivering speeches written in large part by aides. Despite her observation that she pays taxes just like the next guy, the profits from this hard work went into tax shelters that the Clintons claim to oppose as the refuge of One Percenters. Bloomberg reported that the Clintons managed to ease their struggles by exploiting the same estate-tax loopholes they oppose as a form of “evading taxes,” as do Democrats in general in their income-inequality crusade.

Not too many of the hoi polloi will identify with that kind of “struggle” faced by the Clintons, and that’s precisely the problem for Democrats this year, as well as in 2016. Ever since Mitt Romney began his run for the presidency, President Obama and the Democrats made him a personal target for their income-inequality political messaging campaign. They painted him as a clueless One Percenter who couldn’t possibly relate to middle-class voters. They spent the summer of 2012 attacking the business he built, even though it created middle-class jobs and invested in private-sector success stories like Staples.

With ObamaCare a disaster, the economy still stagnant, and Obama’s foreign policy collapsing, Democrats running in red states this year need to maintain the demagogic income-inequality theme. They have little else to cling to. Suddenly, though, the party’s presumed front-runner for 2016 has turned into a comic figure, someone akin to what Democrats imagined Romney to be. She laments the struggle of earning eight figures in a single year after leaving the White House and entering the Senate, while giving Sawyer a guided tour of her $5 million home in Washington, D.C. It doesn’t get much more tone deaf than this.

Hillary Clinton is a living example of the hypocrisy of Democratic rhetoric and the attacks on Romney’s character, at a moment in time when Democrats can least afford it. Chris Cillizza notes that Clinton is handing Republicans the issue “on a silver, ahem, platter.” Ouch.

She’s the poster child for income inequality and the cluelessness of the One Percenters, which all but eliminates that argument for Democrats as long as she has her Unprecedented Lead in the Field Of One. Her mediocrity and cluelessness will expose the hypocrisy and the demagoguery of the Democratic Party’s class warfare, all the more so to the extent that Democrats are forced to explain away Hillary’s bumbling. Without that, they’re toast in November, and possibly in 2016 as well.

Update: Ana Marie Cox believes that Hillary’s dissembling is an even greater threat:

The real mystery of her present disingenuousness is that there’s really nothing shameful, in and of itself, about the kind of wealth the Clintons have accumulated. As Bill himself said just the other day, “Americans don’t resent other people’s successes.” And polls show that Americans still love rich people! In 2012, 92% of people describing themselves as middle-class and 84% of self-described lower-income people said they admired the wealthy. Whenever Hillary denies she one of them, she just proves the point of the 34% of Americans who say the wealthy are less honest than the rest of us.

Simply being rich isn’t insulting; pretending you aren’t is.

Clinton’s ongoing misrepresentations – an unwillingness to accept and acknowledge that her life in politics has been not just educational but lucrative – reflects the central conundrum of Hillary Clinton, campaigner: she thinks she’s earned your vote because she’s worked hard and studied and has a 4.0 GPA, but she doesn’t quite believe that votes always go to those who’ve earned them. Indeed, that was, for the Hillary camp, the lesson of 2008.

And so she undercuts her legitimately impressive career with false modesty about the very quality that one can quantify: wealth. The thing about running for president and not head of the class is that she can’t show us her grades or awards of merit. Her boasts of competency – 3am phone calls and navigating world diplomacy – require a certain amount of faith in her word; when she tells us she’s broke, we know she’s lying.

It makes her look like she’ll say anything to get her hands on power, and that’s not exactly a winning perception in American politics.

Update: Made a couple of minor edits and added a qualifying statement in the original conclusion regarding Democratic apologists for Hillary.