The Late Show: Venus Williams’ Bittersweet Night at the US Open

The US Open has long been a showcase for tennis’s most elite, but Monday morning’s matchup between Venus Williams and Sofia Kenin brought a different kind of spotlight to Arthur Ashe Stadium. A record-breaking 12:13 a.m. kick-off was just one aspect that made this match stand out.

Williams’ loss marked her sixth consecutive defeat at the US Open since her first-round win in 2019, and her 14th straight singles loss dating back to July 2025. These recent trends have left many wondering if Williams can continue competing at a high level. Her remarkable career is still a benchmark for younger players, with seven Grand Slam singles titles and five Wimbledon crowns between 2000-08.

The question now becomes: will we see more late-night matches featuring the likes of Williams and Kenin, or will they become an increasingly rare sight? This loss may have marked a turning point in Williams’ career. If she chooses to continue competing in singles, it’s hard to see how she’ll be able to overcome her recent struggles.

This is not just a story about Venus Williams’ waning powers; it also speaks to the shifting landscape of professional tennis itself. Younger players like Kenin are rising through the ranks and bringing new styles and strategies to the sport. The 2020 Australian Open winner, for example, needed only 32 minutes to take the first set against Williams – a testament to her own talent as well as the increasingly fast-paced nature of modern tennis.

The late start was far from the only anomaly in this match. In fact, it became the latest finish for a first-round women’s match in US Open history. This adds another layer to the story: even as the game itself becomes faster and more high-octane, its top stars are struggling to adapt.

The Williams sisters’ storied doubles career is also worth keeping an eye on. They’re expected to compete again this year after receiving a wild-card entry – but will they be able to recapture some of their former magic? With Serena’s own singles career now in decline, it’s clear that even the most decorated players must eventually pass the torch.

As we watch the likes of Kenin and other young stars take center stage, it’s hard not to feel a sense of nostalgia for an era that seems increasingly distant. But perhaps this is what tennis needs – a new generation to shake things up and bring fresh energy to the sport. Only time will tell whether Williams’ late-night exit marks the beginning of a new chapter in her own story or the end of an iconic era altogether.