James Reynolds

Chief Executive Officer, Loop Capital

The Chicago-based investment bank Reynolds co-founded in 1997 has become one of the country’s most influential minority-owned financial institutions. Loop Capital made its name in municipal finance, underwriting and advising on large-scale public projects where politics, capital markets and community impact intersect.

But lately, Reynolds has increasingly pushed beyond traditional banking into development bets. In 2023, Loop broke ground on a $90 million film studio complex on Chicago’s South Side, a project Reynolds framed as both an economic catalyst and a corrective to decades of underinvestment in the area. The studio has positioned Loop as a direct participant — not just financier — in neighborhood-scale redevelopment, tying the firm’s fortunes to execution risk rather than advisory fees alone.

That ambition has traveled beyond Chicago. Reynolds emerged as part of a Black-led investment group seeking to redevelop the Oakland Coliseum site after Major League Baseball’s A’s announced plans to leave the city. The proposal drew national attention — as well as lawsuits from group members alleging governance and financing disputes — and highlighted the complexity and scrutiny that come with megaprojects tied to civic identity and public land.

Back home, Reynolds’ name has surfaced in discussions around potential South Side stadium development for the Chicago Bears, as he has tried to facilitate talks for a project that could keep the NFL team in the city. The effort accents his role as a connector between institutional capital, sports franchises and municipal leadership, even when deals remain speculative.

— Sam Lounsberry