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By Jill Filipovic, Author, "The H-Spot: The Feminist Pursuit of Happiness"

Sen. Kamala Harris, the second-ever black woman to serve in the senate, is running for president — and, while her prior prosecutorial career is peppered with groundbreaking moments, it’s also turning into her greatest liability as people across the ideological spectrum are increasingly questioning America’s punitive criminal justice system.

Because Harris is a woman of color running for a position that has been exclusively male (and nearly exclusively white) for its entire history, it can be difficult to parse where she is rightly being held accountable for the damaging choices she made as first a prosecutor and then as California’s attorney general, and where she’s being held to a higher standard and picked apart in ways white men have not been.

First, it’s important to look at her political career in two interrelated contexts. Ambitious women routinely run into the tough-but-likeable conundrum, needing to be seen as both hyper-competent and inevitably agreeable even though, for women, those qualities are usually considered mutually exclusive. This is even more complicated for black women, who are stereotyped as angry, aggressive and anti-white — Michelle Obama, of all people, was often painted as a rage-filled militant by right-wing media despite her inarguably funny, gentle and (frankly) mom-like public disposition. Black women also have to further demonstrate that they are rational instead unreasonable; rationality is simply presumed of white men, unless proven otherwise (and often even after there’s ample evidence to the contrary).

And so Harris’s candidacy— more than that of any other candidate in the field right now — demands difficult and thoughtful conversations on both criminal justice policy and race and gender. These conversations require moving beyond simplistic taglines like “progressive prosecutor” or “Kamala is a cop.” Unfortunately, a temperate and thoughtful parsing seems unlikely from a left still engaging in proxy wars for 2016’s Hillary Clinton v. Bernie Sanders primary.

In a devastating piece in the New York Times, law professor Lara Bazelon detailed the many ways in which Harris’s positioning of herself as a “progressive prosecutor” is a generous rewrite of her own history. As San Francisco district attorney, Harris’s office often took aggressive stances on upholding convictions, even where there was evidence tampering or suppression, which may have kept wrongly-convicted people in jail for decades. She defended the state’s death penalty law, even as she said she personally opposed it – possibly because, early in her career, she came under attack for declining to pursue the death penalty for a man who killed a police officer.

And, when Californians were voting to reform their punitive Three Strikes law, Harris didn’t take a position, citing a conflict of interest — a move many advocates of reform saw as cowardly. She defended the Department of Corrections when they refused to provide gender confirmation surgery to transgender inmates, a policy with which Harris said she personally disagreed and tried to change behind the scenes, but that, as attorney general, she was obligated to represent before the courts.

But Harris also started a program that sent young people convicted of low-level offenses to apprenticeship and job training programs rather than jail. She spearheaded a statewide implicit bias and procedural justice training in an effort to make law enforcement fairer. She often did decline to pursue harsh sentences. She made statistics on police shootings available to the public.

All of her decisions, good and bad, are worth discussing and debating. For many on the left, Harris’s decisions as a prosecutor are disqualifying in a Democratic primary.

But it’s also the case, less often discussed, that Harris was balancing demands and expectations that are not put quite so squarely on the shoulders of white men. As "a woman who is a minority who is anti-death penalty” (her words), she faced significant hostility in her job and during her campaigns from police unions and the law-and-order types in her state, including Sen. Dianne Feinstein. Harris is now criticized for being too deferential to existing authority in her work. That may be true — but it may also be true that she simply had less space to be unrestrained.

Because there have been so few women generally, and women of color specifically, in positions of high-level political power in the United States, it becomes easier to caricature them or flatten their records into simplistic positions rather than taking into account the nuances of policy. White men, on the other hand, get to be complicated, have imperfect records, and be treated like individuals.

For instance, in 2016, Hillary Clinton took significant heat from the left for speaking in favor of the punitive 1994 crime bill as First Lady: Even though she had no power to actually vote for the bill, it dogged her campaign anyway. Her primary opponent, Bernie Sanders, however actually did vote for the crime bill, but largely escaped criticism for his vote because, well, it was “complicated.” And that’s true: It was complicated.

Sanders said at the time the bill was being considered that the country’s priorities were misplaced and more attention should be paid to jobs and education than punitive punishments. He said during the 2016 primary that he nonetheless voted for it because there were other provisions, like the Violence Against Women Act and assault weapons ban, that he thought were important. But before his presidential run, he'd also bragged about voting for the bill as evidence of his “tough on crime” stance. All of his explanations have been largely accepted.

Female candidates are often not extended this same benefit of the doubt, let alone the understanding that sometimes, politicians compromise or make mistakes. However, being both human and politicians, they are guaranteed to have made decisions that are craven or simply wrong-headed, as have their male counterparts. The question, particular for those on the left, is how to hold politicians accountable for the choices they made that did significant harm without falling into the trap of giving more credence and understanding to white men’s decisions, and not understanding the particular demands facing women and people of color in politics.

Conversations around Harris have to both offer a critical but fair reading of her time as a prosecutor — when she led offices that did significant damage to vulnerable people — while also allowing for a nuanced conversation on the many ways race and gender still shape both political opportunities and perceptions.

That doesn’t means that liberals are required to support Harris or whitewash her record, and indeed a reasonable and responsible debate about her candidacy requires asking tough questions about the choices she made. But a reasonable and responsible debate also requires asking tough questions of the men whose choices we have long let slide, and understanding that one’s race and gender continue to impose outside limits on what one is able to do without consequence.

That’s a more difficult and measured conversation than edgy hashtags allow. But if we don’t want 2020 to be a repeat of 2016, it’s a necessary one.