It was easier to write about Hillary Clinton when I hated her.

I spent much of the 2008 Democratic primary season furious at both Clinton and the second-wave feminists who tried to guilt young women into voting for her. In Barack Obama, I thought, America had the chance to elect a transcendent figure, a person who promised so much more than the relentless triangulation of Bill Clinton’s disillusioning presidency. It was inexplicable to me that, presented with Obama, anyone could prefer Bill Clinton’s wife. Mocking Obama’s promise to unite the country, Hillary Clinton said then, “The skies will open, the light will come down, celestial choirs will be singing, and everyone will know we should do the right thing and the world will be perfect.” She didn’t just fail to inspire—she seemed to sneer at the whole idea of inspiration.

I kept a mental list of every disappointing thing Hillary Clinton had ever done, from supporting welfare reform to voting for the Iraq war to co-sponsoring a Senate bill to ban flag-burning. I wrote article after article inveighing against the idea that Clinton was a feminist standard-bearer. In fact, I argued, she exemplified “a phenomenon seen in many developing and crisis-ridden countries: the great man’s wife or daughter promising to continue his legacy.” I was livid when older feminists like Gloria Steinem, Robin Morgan, and Linda Hirshman denigrated the young feminists supporting Obama. “If feminism equaled supporting Hillary Clinton, I’m not the only one who wouldn’t want anything to do with it,” I sniffed.

It is strange, then, to find myself, eight years later, not only rooting for Clinton, but feeling exasperated by her left-wing critics. I know their case against Clinton. I agree with a lot of it. I worry about what Clinton’s many flaws would mean for a potential presidency. Now, however, watching her be rejected by young people swept up in an idealistic political movement, I feel sadness instead of glee.

Partly, this is because circumstances have changed. The Clinton of 2008 was running for her husband’s third term, touting her record as first lady as a qualification. Since then, she’s carved out a distinct record as secretary of state. She is running as a continuation of the Obama administration; the fact that she’s married to Bill Clinton is almost immaterial.

Her message is different too. The last time she ran for president, she entrusted much of her strategy to the odious Mark Penn, who suggested she model herself on Margaret Thatcher, playing up her toughness. Voters don’t want a “first mama,” he wrote, but are “open to the first father being a woman.” This time around, she is emphasizing feminism, putting paid leave and equal pay at the center of her campaign, even coming out against the ban on federal funding for poor women’s abortions, long a political third rail. Watching her run as a champion of women’s rights, I’ve started to get legitimately excited about the possibility of a female president.

Perhaps most significantly, Clinton is running against a very different opponent this time around. Barack Obama is an epochal political talent who promised to expand the Democratic coalition. Bernie Sanders is a mensch whose politics are more or less my own, but I’m convinced he’d be eviscerated in a general election. I know that the Sanders camp believes they can turn out people who’ve become alienated from the political process. As long as I’ve been following politics, it has been a left-wing fantasy that legions of disconnected non-voters will suddenly flood the polls if they’re offered a sufficiently progressive candidate. I’ve never seen anything save wishful thinking to back it up.

Still, sometimes I’m tempted to feel the Bern. It certainly seems more fun to be on the side of political revolution than dour pragmatism. But I just can’t make myself believe. That means I’m invested in Clinton, with all her many faults. And being invested in Clinton, it turns out, is excruciating.

Since the 2008 election, I’ve grown more understanding about why Clinton made some of the ugly compromises I once held against her. Last year, I wrote a cover story for the Nation about her sometimes vexed relationship with the left. Reading biographies of her and histories of her husband’s administration, talking to people she worked with, and revisiting news stories from the 1990s, I was reminded that before she was excoriated as a sellout corporatist, she was excoriated as a feminist radical. She was widely seen as being to her husband’s left, in a way that threatened his political viability. Time after time, under intense pressure, she would overcorrect, trying to convince a skeptical mainstream press that she was a sensible centrist. Eventually, her tendency toward triangulation became almost instinctive.

Since the ’90s, of course, American politics have become far more polarized, and the Democrats have moved left. The result, for Clinton, is an almost tragic irony. She’s now struggling to convince voters that she is the person she was once widely assumed to be. A more adroit politician might be able to do this, but that would require leveling with the electorate, and this Clinton cannot do.

I don’t blame Clinton for building a carapace around her true self. There is no person in America who has been subject to such constant, withering public dissection. Tens of thousands of words have been devoted to sneering at her hairstyles. She’s been jeered at for her laugh, her wrinkles, her ankles, her clothes. The entire planet knows that her husband cheated on her. The media proclaims, over and over again, that people simply don’t like her (though she was recently voted the most admired woman in the world for a record 20th time). Of course she has trouble letting down her guard! Without an enormous capacity for self-protection, how would she have survived a level of public ridicule that would have driven any other woman insane?

Knowing that, however, doesn’t change the fact that Clinton is not a very good politician. Whenever she’s boxed in, she stonewalls or pivots to crude demagoguery. During a Democratic debate in November, she invoked 9/11 to justify her ties to Wall Street. Just last week, she tried to argue that she can’t be part of the political establishment because she’s a woman. She is refusing to release transcripts of her speeches to Goldman Sachs, even though it’s hard to imagine that anything in them could be more politically damaging than her insistence on secrecy.

A more agile Democrat might be able to take a page from Donald Trump, and argue that it’s precisely her experience with a corrupt system that positions her to change it. She could say she wants to appoint Supreme Court justices to overturn Citizens United, but while it stands she’ll use all the tools available to fight for her political vision. She could give a speech about how, as a woman, she’s often felt like an outsider even when she was at the very center of world power. She might describe what the glass ceiling looks like when you’re right underneath it.

It’s understandable that, after all she’s been through, Clinton has a hard time being frank and open with voters. But it’s still a problem, for her and for those of us who want her to win. Part of what’s so frustrating about being a leftish Clinton supporter is that much of what her progressive critics say about her is true. She’s a hawk. She spoke in favor of welfare reform during her husband’s presidency. She believes Wall Street has a significant role to play in the economy. She’s cautious and calculating.

There are other things about her that are also true. By most accounts, she accepted her husband’s pursuit of welfare reform grudgingly, after her attempt to create a universal health insurance program was blamed for the disastrous 1994 midterms. Her overall voting record in the Senate was to the left of both Obama and Joe Biden. She’s defied her billionaire backer Haim Saban to enthusiastically support Obama’s nuclear deal with Iran. She has been a staunch, consistent defender of reproductive rights.

For a progressive, how you reconcile conflicting truths about Clinton depends, to some extent, on how much you empathize with her. Supporting Clinton means justifying the thousands of concessions she’s made to the world as it is, rather than as we want it to be. Doing this is easier, I think, when you are older, and have made more concessions yourself. Indeed, sometimes it feels like to defend Clinton is to defend middle age itself, with all its attenuated expectations and reminders of the uselessness of hindsight.

Empathizing with Clinton, however, is a painful business. It means wincing along as she endures yet another round of public humiliation, another batch of stories about women’s indifference to her feminist appeal, another explosion of punditry about her lack of charisma. It means being constantly reminded that people on the left as well as the right find aging women pathetic. It means watching the Sanders phenomenon, in most ways a hugely welcome renaissance of American socialism, with dread as well as delight. There was no shame for Clinton in losing to Obama. But the fact that she’s fighting for her political life against Sanders, a man who initially joined the race more to make a statement than to contend for power, is a mortifying public rebuke.

There’s no way to know how much of this rebuke is about Clinton the individual, and how much about Clinton the woman. Al Gore endured similar media derision over his inability to fake authenticity. He was scorned by progressives who were convinced that legions of non-voters were prepared to rally behind Ralph Nader. But the fact that Clinton is the first woman to have a conceivable chance of winning the presidency gives the contempt with which she is treated an extra sting. She’s contorted herself so many times to meet the shifting demands our culture makes of women in public life. I understand why so many now see her as someone who can’t be trusted. But I’ve also come to understand the forces that made her that way.

Read more of Slate’s coverage of the 2016 campaign.