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Bernie Sanders‘ newest adviser for his presidential campaign is redefining the answer to the question, “tough day at work?” Barely two days on the job and Phillip Agnew, a renowned pro-Black organizer and activist, was already having to explain himself over a series of tweets from years ago during President Barack Obama‘s two terms in the White House.

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But instead of being able to immediately focus on his new task at hand — helping Sanders edge out Joe Biden for the Democratic nomination by advising the campaign how to eat into the support the former vice president has with Black voters — Agnew has had to spend his time apologizing for his Twitter sentiments that focused on former first lady Michelle Obama.

Agnew may have foreseen the Twitterstorm of controversy that would come with the announcement of his new position. He posted a picture Saturday on Instagram of the press release making the announcement and captioned it in part by saying he took “this role knowing the challenges and contradictions that come with it and im [sic] excited about the opportunity to help craft how we move going forward.”

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our movement is for Black people across age, class, gender and sexual orientation. we've come a long way, and still a ways to go. today, i am proud to announce that after much consideration and consultation i have decided to accept an offer to become a Senior Advisor to the @berniesanders Campaign. _______ i take on this role knowing the challenges and contradictions that come with it and im excited about the opportunity to help craft how we move going forward. to my friends, family, and mentors thank you for your love and accountability in this process. i hope to maintain your pride and respect as i move forward. i see this as a people's position on a people's campaign. my commitment is to our movement, always. _______ i want to thank the leadership on this campaign for having the insight to extend this offer of collaboration. this campaign is the strongest: has the most people, the vision, the energy and the commitment to the People that is required in this moment. Let's move. there's work to do and space here to do it. We will win by leaving no one behind.  That is our promise and commitment. #bernie2020

A post shared by phillip agnew (@philsomething) on

But that was before Twitter sleuths scrolled back more than a decade ago to unearth some really disparaging tweets about Michelle Obama. In separate tweets from 2009, Agnew felt the need to make it known that he found Michelle Obama to be “ugly” and “not pretty.”

Agnew’s past tweets put him in the company of people like failed actress Amanda Bynes, who in 2013 found herself in similarly hot water over tweets calling both Barack and Michelle Obama “ugly.”

The fact that these tweets were resurfaced during Women’s History Month might not be the best look for a candidate who was recently accused by his fellow senator and presidential candidate Elizabeth Warren of being a sexist.

Those comments stood in stark contrast to the glowing words Sanders had in the press release, where he called Agnew “a gifted organizer and one of his generation’s most critical voices on issues of race and inequity. He has and will continue to push me and this movement to deliver on what is owed to Black people who have yet to experience reciprocity in this country.”

In addition to the tweets about Michelle Obama, Agnew also in 2011 tweeted conspiracy theories doubting whether President Obama was truly responsible for having Osama bin Laden killed as well as an Instagram post suggesting the September 11 terrorist attacks against the U.S. were karmically deserved.

The tweets prompted Agnew to issue an apology on Sunday and blame his past social media activity on youthful indiscretions. He said he was only 23 at the time he “tweeted stupid comments about Michelle Obama” and that he wanted “to be accountable for them” by saying he is “sorry” for the tweets he posted “as a young, immature, and insecure boy who thought he was forever invisible and ‘invincible.'” He went on to admit that his “comments were shallow, careless, sexist, and cruel.”

While that may be the end of it for Agnew, there could be lingering damage for the senator from Vermont. It also seemed to be a really bad look for the campaign of Sanders, who has had what CNN described as “an uneven relationship with [Barack] Obama.” The addition of Agnew also came a few days after Sanders released an ad that arguably took President Obama’s words out of context in order to paint a rosier picture of their relationship. Having his campaign hire someone who has also made disparaging remarks about the former president and his wife may not be the most helpful at a time when both Sanders and Biden are vying for Obama’s endorsement.

Agnew first made a name for himself in 2013 as the executive director of the Dream Defenders, a group launched in the wake of the shooting death of Trayvon Martin to build young leaders while fighting for social justice. That same year Agnew was also one of the youngest leaders set to speak at the 50th anniversary of the March on Washington.

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