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The rise of Pete Buttigieg to the top of the Iowa polls has been one of the stranger stories of the 2020 Democratic primary. On paper, a 37-year-old mayor of a small town in Indiana seems to be an unlikely competitor to a star-studded cast of heavyweight senators, governors and celebrity billionaires. But Buttigieg has shot to the lead in Iowa through a blitz of advertising in the state and a mild-mannered polite charm that has proven effective with many older white voters.

Buttigieg has also been the beneficiary of some caginess among Iowans about the other national frontrunners. Joe Biden’s gaffes on the campaign trail have been numerous, and the national press speculates endlessly about when, not if, his support will collapse at a national level. Bernie Sanders has been on a recent upswing, but still faces daunting questions about whether he can expand his coalition, and whether he will suffer in a general election for taking the most unabashedly progressive stances in the field–including, for instance, openly saying he will raise taxes on the middle class to pay for Medicare for All even if their overall costs will go down by getting rid of their private insurance premiums. Elizabeth Warren’s campaign has hit a snag over healthcare in an attempt to maintain true to the promise of Medicare for All without raising taxes on the middle class and provide a more realistic onramp to it, which has angered activists both on her right and on her left. And none of the rest of the field has caught significant traction for a variety of reasons.

That leaves Buttigieg, whose carefully managed persona offers the combination of a less inspirational version of Obama and a less risk-prone version of Biden that is particularly attractive to older white voters who want a return to what they consider to be normalcy. At a policy level, Buttigieg has consistently attacked Warren and Sanders from the right, portraying their healthcare plans as overly ambitious, and using a faux-populist argument in favor of means-testing free college instead of making it universal or nearly universal. While this has infuriated most younger and more progressive Democrats, it has a certain appeal to voters comfortable with this sort of triangulated politicking–even if it has so far fallen flat with people of color, young voters and other groups. As Michael Sayman elegantly put it, “Buttigieg is what Boomers wish Millennials were like. Bernie is what Millennials wish Boomers were like.”

But Buttigieg himself has managed until recently to avoid the spotlight as his rivals have tended to focus more on one another. That changed this week as Buttigieg’s employment history and private fundraisers with wealthy donors have come under greater scrutiny by competitive campaigns. And so far, Buttigieg has seemed ill-prepared for the closer attention.

The first major issue is his work for the secretive consulting company McKinsey. For an older politician, delving into work history from their 20s would seem to be a bit of a cheap shot. But for a candidate with a resume as thin as Buttigieg’s the work from his gig with McKinsey spans a fifth of his working career. And McKinsey itself has faced appropriately withering criticism for recommending that ICE treat their detainees even more cruelly than ICE was already comfortable with, among other distasteful work. If Buttigieg built his career servicing such clients, that might not be disqualifying but it’s certainly something voters seeking a candidate to save the country from Trump might want to know about before casting their votes.

For his part, Buttigieg has claimed that he is bound by an non-disclosure-agreement with McKinsey that prevents him from revealing the clients he served or the details of his work. But as with Trump’s tax returns, it’s difficult to imagine that rationale will survive for long–and in any case it makes the candidate look like he has something to hide. It hasn’t helped that Buttigieg’s main response has been to try to deflect to the past records of other candidates rather than offer a reasonable explanation of his work beyond that he “never worked on a project inconsistent with my values.”

Perhaps more troubling is Buttigieg’s refusal to provide transparency about his private big-dollar fundraisers, especially in a race where the other leading frontrunners have either eschewed them entirely or lessened their reliance on them. Per the Huffington Post:

Pete Buttigieg struggled to explain why he does not open up his high-dollar fundraisers to the media or why he no longer discloses the names of his campaign “bundlers” during a brief press conference Friday night. Buttigieg, the mayor of South Bend, Indiana, clearly understands that there is some public benefit to knowing the names of high-dollar donors. After all, he began his campaign by publicly releasing the names of his “bundlers,” the super-donors who give and raise large amounts of money for a candidate. But he has not updated his public list of bundlers since April, according to the Center for Responsive Politics.

The challenge here is that voters are rightly skeptical of the role of big money from wealthy donors in politics. Candidates on the left are trying to avoid it with small-dollar fundraising to prove they aren’t accountable to undue influence or special interests. And even alleged billionaire candidates from Trump to Bloomberg have put their own spin on this populist card, claiming that their wealth makes them unaccountable. It’s good politics right now, an ethical step in the right direction. But it’s one that Buttigieg has pushed aside.

And it’s clearly a soft spot for the campaign that the candidate was not expecting. So much so that when pressed on the issue he delivered a series of increasingly bizarre Zuckerbergian non-answers almost tailor-made to reinforce the stereotype of an overly ambitious professional young climber:

This clip of @PeteButtigieg, responding to questions about why he won’t open his fundraisers to the press, is devastating. Wow. pic.twitter.com/mZ2HipoQXA — phil (@PrettyGoodPhil) December 7, 2019

The transcript went as follows:

Earlier today, you said you were open to having a conversation about opening your fundraisers. And that’s a question that reporters haven been asking for months now so I’m wondering when do you expect to actually be able to have that conversation and give like an answer on that? Again, I don’t have a timeline for you. As the candidate, can’t you just direct your campaign to open those fundraisers? What’s that? As the candidate, can you just direct your campaign to open those doors? Yes. Why haven’t you done so? What’s that? Why haven’t you done so? There are a lot of considerations. And I’m thinking about it. Can you give us an example of those considerations? No.

How this will all play out with voters in Iowa and beyond is anyone’s guess. But it’s not a good first few moments in the spotlight for a candidate seeking to punch above the weight of their resume.