Battle Ready or Battle Weary?

A conversation with Stuart Duguid, organizer of the "Battle of the Sexes" between Aryna Sabalenka and Nick Kyrgios, on its risks and rewards.

After a torpid start over the weekend, the WTA Finals have kicked into gear nicely in the last couple of days, ramping up with a pair of stellar battles between Top 5 players.

A few hours ago, fourth-ranked Amanda Anisimova again showed resilience against second-ranked Swiatek, coming back from a set down to win in three sets and book her spot in the semifinals. For Anisimova, a second straight win over Swiatek makes it seem like the double bagel she infamously swallowed in the Wimbledon final was just her carbo-loading for later triumphs.

For my money, the best match of the week so far had come a day earlier, when top-ranked Aryna Sabalenka held off fifth-ranked Jessica Pegula in three sets on Tuesday evening. The two also played a sparkling semifinal at the U.S. Open a couple months ago, and though the head-to-head is clearly in Sabalenka’s favor at 9-3, their match-up has been one of my favorites to watch this year.

But when I started getting media requests to appear to discuss Sabalenka a few hours later, it had nothing to do with her stellar win in Riyadh, or her dominant season in which she has already sewn up the year-end No. 1 ranking for a second consecutive year. Instead, it was about some news that the agency representing Sabalenka, Evolve, had announced earlier that day: the WTA No. 1 will be ending her year with a “Battle of the Sexes” match against another Evolve client: ATP No. 652 Nick Kyrgios, who has only won one ATP singles match in the last three years.

Chatter about this match had begun a few months ago, but now that a time and place had been set to make it official—December 28th in Dubai—the event spawned headlines that quickly broke out of the tennis bubble. I had wanted to ignore this match, honestly, but felt like I no longer could.

There has been a smattering of “Battle of the Sexes” matches staged in tennis history, but the most-remembered one—Billie Jean King’s 1973 win over Bobby Riggs—was considered foundational in establishing the fledgling women’s tennis tour.

Billie Jean King and Bobby Riggs in 1973.

When that match became an international phenomenon and cultural flashpoint more than a half-century ago, the notion of female professional athletes was still a new, unproven idea. King’s win—albeit over a 55-year-old man who was three decades removed from his last major title—helped women’s tennis gain tremendous recognition and credibility, and was also credited with empowering the broader women’s movement of the early 1970s.

Knowing the history well, 52 years later, I wasn’t sure what could be gained from reheating this recipe. Thanks to King’s pioneering, women’s tennis has minted multitudes of millionaires. Sabalenka has already earned $42 million in prize money alone in her career, including $5 million for her most recent U.S. Open title a couple months ago. Women’s tennis is an established success story, and there would seem to be far more for Sabalenka (and the whole of women’s tennis) to lose than to prove in this match, since there are still many loud detractors who resent the growing prominence of women’s sports.

One of them, specifically, will be across the net: Kyrgios has a history of belittling women and women’s tennis. When asked about the rumored “Battle of the Sexes” on a podcast appearance last month, Kyrgios had said he was going to “put Sabalenka in her place.” What place, exactly, should the WTA No. 1 be put in? Why, I wondered, would she and her agent agree to such a thing?

I know this agent well, fortunately, so before the first of my media hits about this ballyhooed Battle of the Sexes, I reached out to Stuart Duguid, founder of Evolve, to learn more about how and why it came together. Duguid, who broke away from IMG to start the new agency in 2022 with his first star client Naomi Osaka, has represented Kyrgios for years and began working with Sabalenka this year.

I’ve known Duguid for years—he was a big help during the writing and fact-checking of my biography of Osaka, particularly—and so I was eager to talk with him about this new venture, both about how the intriguingly specific parameters of this novelty match were hammered out, as well as my misgivings about the basic concept.

“I like doing experiments, I like taking risks, I like doing things other people haven’t done. I don’t like sitting back and doing the status quo. And my players have the same appetite, and I’m gonna encourage that and not thwart it.” -Stuart Duguid, Evolve

Duguid shared his vision, where he saw reward where I saw risk, and addressed my concerns. The result was a spirited conversation which I am happy to share for subscribers below, as well as video of my hit on ABC (Australia) television on the topic.

To read our whole conversation, including a nifty graphic of the unique court design for this match, please subscribe to Bounces! -Ben