Oprah Winfrey mixed nostalgia with a rare glimpse into her famously private relationship as she reunited with former colleagues from The Oprah Winfrey Show in Chicago.
The television icon was joined by longtime partner Stedman Graham during a gathering marking 15 years since her groundbreaking daytime program ended its 25-season run. The celebration also arrived just weeks before another major milestone: the 40th anniversary of the show’s nationally syndicated debut on Sept. 8, 1986.
The reunion was held at Reunion by Chef Art Smith at Navy Pier, bringing Winfrey back together with members of the team who helped turn her talk show into one of television’s most recognizable programs.
Winfrey thanked her former colleagues as the group looked back on their years together, making the occasion as much a celebration of the people behind the cameras as the woman who became the show’s household name.
Adding another layer of nostalgia was Graham’s presence. He and Winfrey have been together since 1986, meaning their relationship has unfolded across essentially the same four decades that transformed Winfrey from a Chicago television host into an international media figure.
Despite their longevity as a couple, Winfrey and Graham are rarely fixtures on the celebrity-event circuit. Their appearance together in Chicago therefore offered an unusual public glimpse of a relationship they have largely maintained outside the spotlight.
The couple’s previous widely reported event appearance together came in October 2019, when they attended the grand opening gala for Tyler Perry Studios in Atlanta.
Winfrey and Graham first crossed paths at a charity event in 1986. Friendship eventually turned into romance, and the couple became engaged in 1992. They later decided not to marry, a choice Winfrey has discussed openly over the years while expressing satisfaction with the partnership they created instead.
Their Chicago outing brought those parallel histories together in fitting fashion. Winfrey was celebrating the television show that transformed her career with colleagues who helped make it happen, while Graham, the partner who has been alongside her since that pivotal first year, joined the occasion.
Forty years after both chapters began, the reunion offered a reminder that some of Winfrey’s longest-lasting relationships, professional and personal, have endured well beyond the final credits of her legendary talk show.
