Anna Wintour and Spike Lee Lead Star Power at US Open Gala

23 August 2025

Andre Agassi will be honored at the US Open gala. Susan Mullane-Imagn Images

On August 23, the USTA Foundation hosted its annual opening night gala for the US Open at Arthur Ashe Stadium’s prestigious President’s Box, and Hollywood’s heavy hitters made sure their presence was felt. Among the luminaries expected were fashion’s queen Anna Wintour, visionary filmmakers Spike Lee and Alec Baldwin, style doyenne Vera Wang, music icon Tina Knowles, former heavyweight champion Mike Tyson, and design-world darling Gabriela Hearst. If that weren’t enough, UK favorite Charlie Cox known for his role in Daredevil also graced the guest list. All of this glamour unfolded under the guidance of emcee Gayle King.

Beyond the glitterati, tennis royalty also played a role in setting the tone for the evening. Board chair and legend Chris Evert took center stage to present the Serving Up Dreams Award to another icon, Andre Agassi, just as the singles matches were gearing up to begin. The ceremony beautifully fused competitive spirit with heartfelt homage reminding everyone that tennis remains woven through generations.

Page Six chronicles offer a glimpse into the event's legacy and appeal. Anna Wintour, Alec Baldwin, Vera Wang, and others have become familiar faces at the gala, often serving as the evening's cornerstone. In the past, notable names such as Hugh Jackman, Katie Couric, and even former New York mayor David Dinkins have joined the fold, adding to the event’s distinguished pedigree.

These evening affairs are about so much more than appearances. They help sustain the USTA Foundation’s charitable mission, supporting career development and tennis access for underserved youth. The gala gracefully positions the game as both exclusive sport and community touchstone an exchange of purpose wrapped in pageantry.

As one glances at the guest roster, it’s clear the gala isn’t just a tennis gala it is New York’s social calendar brought courtside. Wintour’s immaculate poise, Spike Lee’s cultural artistry, Agassi’s legacy, it’s a collision of worlds: athletics, art, fashion, and philanthropy, all meeting under tennis’s white-hot favor.

With the singles action beginning, the gala served as a fitting overture an ode to glamour, achievement, and the enduring draw of Wimbledon’s thunderous American cousin. And for anyone in the stands or watching at home, the spectacle proved one truth: tennis isn’t just about winning sets. It’s about shining, every step of the way.