Joe Biden frequently points to his time serving as President Barack Obama’s vice president as part of his pitch to voters, and it’s easy to understand why: The most consequential chapter of Biden’s long political career has been his time as the still-popular Obama’s No. 2.

Now, in Biden’s third race for the Democratic presidential nomination, he has consistently been the leader of the pack. For his rivals, that means he is their main obstacle. By the transitive property of politics, knocking down that obstacle will require taking shots at some of Obama’s policies.

And so they did, repeatedly, on Wednesday night during the Democratic presidential debate. That prompted Biden onstage and many Democrats viewing in the audience to question the wisdom of knocking Obama’s legacy. Here’s how The Washington Post’s Michael Scherer described it:

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Like young adults seeking to break away from their father’s shadow, the candidates who gathered in Detroit to debate the party’s future this week repeatedly challenged Obama’s record, both directly and indirectly, as too timid, misguided or insufficient for the moral challenge of the moment.
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Replacing Obama’s signature accomplishment, the Affordable Care Act, has become the primary policy goal of many of the leading 2020 contenders. Several others have attacked Obama’s efforts to secure a new trade deal with Asia, his decision to surge troops into Afghanistan and the practice of courting wealthy donors, which anchored both of Obama’s campaigns for president.

Biden did seek distance from some individual Obama-era policies, prompting Sen. Cory Booker (N.J.) to tell him he can’t have it “both ways.” Biden made a point to call out the attacks as dings at Obama policies.

“I hope the next debate we can talk about how we fix the things that Trump has broken, not how Barack Obama made all these mistakes,” Biden said to reporters on Thursday.

Biden believes the best way for the Democrats to defeat the Republicans — and pick up swing voters — is to attack Trump’s unpopular presidency. Liberals say conventional wisdom isn’t sufficient and they have to be bold in putting forth a vision that general election voters will get behind. But to get there, they have to beat Biden first — and that means attacking his political career, including his time as a senator as well as his vice presidency.

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Obama is still very popular, and his presidency is viewed favorably, especially among the left. But they do view parts of his presidency as insufficient and imperfect. To some of the Democratic base, the Obama administration was not “progressive” enough on issues related to immigration, war and criminal justice reform. They criticize the administration for high numbers of deportations, engagement in the Middle East and perhaps dragging its feet in investigating police shootings of people of color.

Candidates seeking to boost their candidacy seized those topics Wednesday night.

New York Mayor Bill de Blasio asked Biden his thoughts on the Obama administration’s record on deporting undocumented immigrants. “You were vice president of the United States,” he said to Biden. “I didn’t hear whether you tried to stop them or not, using your power, your influence, in the White House. Did you think it was a good idea, or did you think it was something that needed to be stopped?”

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And Julián Castro, who was housing secretary in Obama’s administration, distanced himself from an Obama-era policy that makes crossing the border improperly a federal misdemeanor crime.

While Biden defended the administration’s law, Castro pushed back, saying: “It seems like one of us has learned from the lessons of the past and one of us hasn’t."

To Biden’s point, many of the swing voters who delivered the White House to Trump after previously voting for Obama, saw the country’s first black president as too liberal — particularly when it came to social issues like support for LGBT rights, protecting what social conservatives call “religious freedom” and how he addressed the presence of racism among law enforcement in America’s criminal justice system.

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The path to the White House for liberal candidates involves boosting turnout among the left’s base, flipping swing voters back to the left, or both. This means that no matter where a candidate is politically on the spectrum of liberal politics, that candidate is probably going into debates trying to appeal to voters who found the Obama administration lacking in some way and want the next Democratic president to address those things.

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Biden is said to have been one of the most hands-on and involved vice presidents in history, Steven Levingston wrote for The Washington Post Magazine. When Obama selected the former lawmaker as his second-in-command, Biden says, he accepted on the condition that he would be the last person in the room when it came to the administration’s biggest decisions. This means Biden probably played a key role in the decisions that were most significant during the last administration — including the bad ones.

So when de Blasio wanted to make the case that he is the best candidate to respond to police violence against black people, he turned to Biden and said the Obama administration did an insufficient job in addressing the issue.

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This infuriates Biden. His critics aren’t totally wrong to say he wants it both ways — magnifying the role he played in the Obama administration to highlight why he is a better option, compared with his competitors, while silencing their attempts to pick apart his experience by claiming it ultimately hurts the Democrats. This strategy may work for Biden, but it is not likely to work for his competitors who want to beat him during the primaries.

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Perhaps those competing for the Democratic nomination will be more thoughtful in how they critique the Obama administration moving forward. They don’t want to risk more voters moved to support President Trump’s long-term goal of dismantling the Obama legacy. But candidates on the left can’t remain silent if they want to win. They have to knock Biden out of the lead if they are going to move forward in their quest for the Oval Office. And perhaps the best way to do that is to point out how his most recent political experience left much to be desired.

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