Money management pro guides Knight Foundation philanthropy

Jai Winston (Courtesy of the McKnight Foundation)
On a rewardingly ironic note, Jai L. Winston, program director at the historically prestigious John S. and James L. Knight Foundation (, states that he finds, in leading the institution’s philanthropic investments, a gift for himself. “I feel,” he readily attests, “fortunate to be in this position.”

The Knight Foundation works to build more engaged communities and promotes journalism, media innovation and the arts. The company’s mission statement reads, “We believe that democracy thrives when people and communities are informed and engaged.” None of which happens without dollars.

In his position, Winston facilitates the Knight Foundation in making a significant difference during these economically trying times, which haven’t been helped one bit by the last presidential election. In fact, practically the first announcement made from the White House was a threat to dismantle the National Endowment for the Arts.

Winston, as an experienced strategic planning and development professional, works with area leaders and communities to invest in projects that attract talent and expand economic opportunity. While Winston’s modesty is creditable, he is in fact an expert with a strong track record to show for it.

At Ariel Investments, a minority-owned money management firm in Chicago, Winston was strategy and corporate development associate in the chairman’s office, helping to lead its vital, national work on financial literacy and minority entrepreneurship.

He helped to devise a citywide financial literacy blueprint working with the Chicago Financial Education Initiative alongside municipal agencies, public schools, community organizations and private sector partners. He has also managed the Black Corporate Directors Conference, an annual convergence of African American directors serving on Fortune 500 boards.

Before Ariel Investments, there was the plum project of 2013’s Presidential Inaugural Committee in the Office of Intergovernmental Affairs. He also acted as the North Carolina deputy finance director for the 2012 Democratic National Convention Committee and as the Illinois deputy finance director for President Barack Obama’s 2012 re-election campaign.

There, among other duties, Winston prepared briefings and staffed President Barack Obama, Michelle Obama, Vice President Joe Biden and members of the Cabinet for finance events. “It was truly a remarkable experience, knowing that you contributed to curating their prepared remarks, the audience, and how they would spend their time at the event.”

He reflects, “It was a privilege” having the opportunity to prepare briefings for White House principals, which required a lot of discipline and attention to detail. He adds, “Not only do you have the responsibility of preparing them an in-depth briefing for the event, you are also responsible for briefing them in advance when they arrive, so they have a topical overview of who is in the room, how much they’ve contributed, the issues they are most passionate about, etcetera.

Winston’s tenure in the Windy City forged an enviable profile. Additionally, he helped support the promotion of the CEO’s agenda for business and public policy programs, accompanying him for speaking engagements on diversity and inclusion, corporate governance and that recurring matter, financial literacy. Winston had his work cut out for him, saying his responsibilities required a lot of time, commitment and dedication. “It required even more attention to detail and precision.”

Graduating from Howard University with a political science B.A. in 2011, he acknowledged that his education went a considerable way toward readying him for this livelihood, not to mention facilitating a virtually meteoric rise. “Being at an institution like Howard University truly taught me the importance of perseverance, resilience and determination. I think those qualities have played a significant role in shaping the direction and success of my career in such a short time-frame.”

Rounding out his background, Winston has been immersed in the arts as well. He serves on the board of the Illinois Humanities Council and is a junior board member of Lookingglass Theater.

Alberto Ibargüen, Knight Foundation president, attests, “Jai Winston’s focus on diversity and inclusion [benefits] Knight in helping to create an even more successful St. Paul.”

Dwight Hobbes welcomes readers’ responses to P.O. Box 50357, Minneapolis, MN 55403