It’s been less than three months since Ashley Allison announced her company, Watering Hole Media, as the proud new owners of The Root, but she’s already establishing herself and her vision for the future of the site, founded in 2008 by Henry Louis Gates, Jr. and Donald E. Graham.
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A political strategist and communications expert with 20 years of experience creating winning campaigns, Allison has made it her life’s work to be an advocate for democracy and racial equity. She brings that passion to our publication, knowing that in a time where more people are turning to digital media for their news and information, it’s important that we tell our stories with integrity.
As we prepare to honor the best and brightest Black leaders at 2025’s The Root 100 celebration, we’re taking a look at the amazing journey of our new leader, Ashley Allison.
Community Roots
Ashley Allison’s roots in communication and politics go back to The Ohio State University, where she earned her bachelor’s degree in journalism and political science.
She began her career in New York City as a special education teacher at the Boys and Girls High School in Brooklyn.
Continuing her education, she earned her master’s in education as well as a law degree in 2011 from Brooklyn Law School. There, she focused on public interest law, including housing rights, voting and democracy, and racial equity.
Allison is a proud member of Delta Sigma Theta Sorority, Inc.
Increasing Black Voter Turnout
Allison’s work in the community helped fuel her desire to get involved in the political process. In 2012, she joined President Barack Obama’s reelection campaign, leading the efforts to increase Black voter engagement in the key battleground state of Ohio. Her winning strategy led to a four percent increase in Black turnout from 2008 to 2012.
Enroll America
When the 2012 campaign ended, Allison’s work was just beginning, as she worked tirelessly to ensure more people secured much-needed access to healthcare through the Affordable Care Act. In 2013, she became Enroll America’s Director of Constituency and Partner Engagement. There, she led a national campaign that helped enroll more than 1.5 million people in the program.
Ashley Goes to Washington, D.C.
Obama’s reelection led Allison to Washington, D.C., when she was chosen to serve as Deputy Director in the Office of Public Engagement for the administration, a role in which she worked closely with the Black community and faith leaders to listen to their concerns and communicate the administration’s agenda.
“We’re the outward-facing component of the White House,” she explained. “We bring folks into the building to make sure they know where the president stands on policies and issues, and what his priorities are. We also host and speak at other events to hear from the public; we want to know what people’s thoughts are on issues that are affecting their community, so that we can communicate them to the president and ultimately make positive changes.”
Biden-Harris Campaign
Allison’s experience as an organizer made her the perfect choice to become the National Coalitions Director for the Biden-Harris 2020 presidential campaign. In her role, she led nearly 300 staff and paid fellows to energize one of the most diverse voter coalitions in history, resulting in historic voter turnout among Blacks, Latinos, younger voters and more.
CNN Commentator
Fans of CNN will recognize Allison as a featured political commentator on the network. There, she brings her unique insight on the intersection of race, politics and policy to the stories that are making headlines. Loyal viewers on both sides of the aisle love the way she speaks truth to power and how she has to occasionally get folks together– respectfully, of course.
“As a staunch supporter of the Republican Party, the left needs more of you. Incredibly intelligent, well spoken, knowledgeable and easy to listen to. Keep it up!!!! We aren’t all hate!😂❤️ ” wrote someone in the comments of a TikTok she posted defending former first lady Michelle Obama’s decision not to attend Donald Trump’s second inauguration.
Black Voters Matter
Allison has used her platform to remind the Democratic Party not to neglect the Black voters who help get their candidates into office and the issues that matter most to their communities.
“Something the Democratic party often gets reprimanded about, particularly by Black voters is you show up four days before the election,” she said during a 2023 appearance on CNN talking about Democrats success in Georgia. “If the party were really to look at the map and see pockets where they could really turn out voters by small investments, because when you haven’t been spoken to for 20 years, 2 minutes goes a long way in an election cycle.”
Bringing Social Issues to Social Media
As more and more Americans turn to social media for their news, Allison saw a need for trusted sources for the truth. In 2024, she founded Watering Hole Media as a positive alternative to the social media misinformation that is often targeted at Black and Brown communities.
“At a time when we’ve never been more politically divided, we need a space that authentically engages Black and Brown audiences in politics through the cultural conversations they are already having in their group chats, in the barbershop, and at brunch,” she said in a statement announcing the launch.
A New Chapter for The Root
In October 2025, Allison had a full-circle moment when Watering Hole Media acquired The Root from G/O Media. The move allowed Allison, a long-time reader, to proudly announce that the site founded by Professor Henry Louis Gates Jr. was Black-owned once again. In a message to readers, Allison shared her commitment to continuing his vision of sharing the Black stories that matter most.
“The Root has always been a part of my journey, not just as a media outlet, but as a home for stories that reflect the fullness of who we are as Black people,” she wrote. “This moment is not just about me, it’s about us. It’s about carrying forward the tradition of telling our stories with depth, authority, and unapologetic honesty.”
Taking Back the Black Narrative
Although times are challenging in the current digital media space, Allison knows that it’s more important than ever to keep the Black community engaged. She has frequently talked about how reading The Root, including previous The Root 100 honoree lists, helped shape her career, and she wants to make sure the site continues to inspire readers.
“Most importantly, when people look at The Root, I want it to do what it did for me: give you a blueprint to be aspirational and inspirational and know that anything is possible, even if you haven’t already encountered it,” she told NPR in an interview.
Show of Support
Throughout her career, Allison has a established herself as an important voice for the culture, which is why messages of congratulations have poured in from politicians, media personalities and more since the announcement of her acquisition of The Root.
“This is about more than media — it’s about truth, culture, and ownership,” wrote attorney Ben Crump on X.
Announcing The Root 100
For the past 16 years, The Root 100 list has been a tradition at the site, our time to honor the year’s most influential Black artists, athletes, activists, politicians and business leaders who are Black history in the making.
This year, Allison surprised many of the 2025 honorees sharing the news of their addition to the list in person, including talk show host Tamron Hall.
A New “The Root 100”
For 2025, Allison is putting her personal touch on The Root 100, removing the ranking system used in years past. The intention, she said, is to make sure all of this year’s honorees know that the work they are doing is important and needed in this moment.
“Everybody on the list is exceptional in what they do, and it doesn’t matter if you’re 1 or 100, you’re doing it,” she told ‘The Breakfast Club’ hosts in an interview.
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