The Venn diagram between Anna Kalinskaya, Jannik Sinner, and Nick Kyrgios now has too many offshoots. In a complicated history together, the present has also been marred by the incidents taking place between this dramatic triangle. In 2020, Kyrgios and Kalinskaya were reported to be dating, before they parted ways. But Kyrgios yesterday made a comment on one of his pictures with Kalinskaya from old times and that comment sparked a controversy. While Kyrgios has been facing a backlash from the fans for what was considered a very offensive comment, what’s also interesting is that both Kyrgios and Kalinskaya might be managed by the same agency.

On May 24, 2024, it was reported that Kalinskaya had signed with Naomi Osaka‘s agency Evolve. The management company for athletes was founded by the Japanese player and her longtime business partner and agent Stuart Duguid. While there was no statement from Kalinskaya herself, Evolve‘s Instagram page shared a few pictures of the Russian star from the streets of New York in glamorous outfits a few days ago.

But if we look back to two years ago, when Evolve was first founded, their first client was a close friend of Osaka – aka Nick Kyrgios. “Kyrgios embodies the types of athletes we want to work with at EVOLVE,” Osaka had said in a statement. “He’s got an unmatched style, passion, and personality that is unlike any other in the sport. We have some big things in the pipeline for him that are very unique and pioneering.”

While the Australian player has not played much in the last two years due to injury, he has been active behind the microphone with his Good Trouble podcast as well as commentary. Kyrgios is still signed on to Evolve, but recently his social media controversies are catching the most attention, like his latest comment on Kalinskaya.

In response to a picture of himself and Kalinskaya on X, Kyrgios wrote “Second Serve,” which many perceived as offensive. It wasn’t the first time the Australian player had made such comments. He once took a swipe at Donna Vekic, who was dating Stanislaus Wawrinka at the time.

“You’re not a bad boy, you are simply a bad person,” Anna Kalinskaya had written in an Instagram post when rumors of her break-up with Kyrgios started surfacing. There was, however, no name mentioned by Kalinskaya. In a contrasting statement, Kyrgios said afterward, “Nothing happened. We just went our separate ways. Unfortunately, things didn’t work out. We had some fun memories.”

When the whole Jannik Sinner doping saga went down, Kyrgios was among the most vocal of those calling for stricter action against the Italian star, who is now Kalinskaya’s partner. “… you should be gone for two years. Your performance was enhanced,” read a part of Kyrgios’ post on X. But the ITIA cleared Sinner of any wrongdoing as the amount of Clostebol in his system was not enough to practically enhance performance. It was also found that Sinner came in contact with the banned substance unintentionally and hence bore no negligence.

However, with the never-ending stream of controversy from Kyrgios, several fans and journalists are having a go at ESPN after the Aussie’s latest comments.

ESPN under fire for hiring Nick Kyrgios after latest Anna Kalinskaya comments

All year long, Kyrgios has appeared in crucial matches as an expert commentator. And while many have praised him for the way he analyzes a game and knows when to speak and when not to, his off-court persona has yet again created a stir. Many have called for action from ESPN immediately.

Journalist Ben Rothenberg wrote, “Honestly a bit surprised to see ESPN didn’t yank Nick Kyrgios off air mid-#USOpen final, seeing his most recent disparaging tweet about a WTA player circulating. Given his history of demeaning women, women’s tennis, and WTA players, it was already a dubious choice to have him.”

While Jon Wertheim posted on X, presumably in reference to the Wawrinka/ Vekic incident, “Nick Kyrgios once made a misogynistic, wildly inappropriate comment about a WTA player, drew the anger of her ATP player boyfriend, his coach, and much of the locker room…but didn’t face real consequence, dismissed, as it was, as youthful indiscretion. That was 2015. He’s 29 now.”

ESPN has made no comments about the situation yet. Neither has Anna Kalinskaya said anything yet. Will the tennis authorities let this situation go without consequences? Only time will tell!