Amanda Anisimova confessed that her “priority is mental well-being” when she stepped away from tennis in May 2023. Yet her 2025 resurgence has been nothing short of poetic. The Freehold Township native has stormed back with four singles titles, reaching two grand slam finals while lifting trophies in Qatar and China. Her comeback echoes resilience carved through pain. But as she now steps into the WTA Finals, fellow American Madison Keys has revealed an Anisimova moment from this season that cuts deep, one that truly breaks the heart.

Madison Keys, drawn in the same group as Amanda Anisimova at the WTA Finals, made her admiration for her compatriot crystal clear. Speaking at her pre-tournament press conference, the World No. 11 couldn’t help but praise the poise and dignity Anisimova has shown, “I think the biggest thing I’ve been most impressed with this whole year of hers, her entire comeback, is the way that she handled the Wimbledon final. I thought she did it with such grace, she handled it so well,” Keys reflected, her tone heavy with empathy and respect.

Those words carried weight, for Keys knows the heartbreak of a major final all too well. Anisimova, crushed by Iga Świątek in a 6-0, 6-0 defeat at Wimbledon, had seen her dream dissolve brutally. Yet, as Keys noted, the young American never lost her composure amid the devastation. “I know being in that position, it’s such a heartbreaking situation. I thought the way she carried herself through it with such grace, I was incredibly impressed by,” Keys added, speaking from the raw wisdom of her own painful experience.

Back in 2017, it was Keys who felt that same sting. In her first Grand Slam final, she faced her close friend Sloane Stephens at the US Open, only to be crushed 6-3, 6-0 in just an hour. For Keys, that loss left scars, but it also built empathy, a shared understanding that only those who’ve stood on that lonely final stage can truly grasp.

Now, years later, the two American powerhouses stand side by side again, not as adversaries but as symbols of perseverance. Both have traveled vastly different roads, yet destiny unites them once more in Riyadh, Saudi Arabia, where the WTA Finals are set to ignite from November 1 to 8, 2025.

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Anisimova, the World No. 4, opens her campaign against Russian-Kazakhstani star Elena Rybakina, while Keys is set to face World No. 2 and Polish dynamo Iga Świątek. Their eventual showdown will mark the very first meeting between Keys and Anisimova on the WTA Tour, a clash brimming with emotional undercurrents and national pride.

For Anisimova, this is her WTA Finals debut. For Keys, it’s another chance to prove her mettle, to rekindle her spark among the sport’s elite. Her journey to the WTA Finals this year has been a road filled with trials and tribulations.

Madison Keys reviews her 2025 season before WTA Finals

In an interview ahead of the WTA Finals, Madison Keys was posed a question that every athlete faces at season’s end: was she satisfied? Her answer carried the calm confidence of a champion. “2025 has been arguably the best year of my career. I’ve had a lot of amazing tournaments, and winning a Grand Slam is obviously at the top of my list. Doing it later in my career has been something that I’m incredibly proud of, but again, there’s just that tennis player inside of me that wants a little bit more,” she admitted.

It’s easy to understand that mindset. Keys joined a rare club this year, becoming one of only three women in the Open Era, alongside Francesca Schiavone and Flavia Pennetta, to win their first major title later in their careers. Her triumph brought a new layer of depth to her story, proof that resilience can bloom even after the prime.

Reflecting on tennis’s greatest icons, she added perspective with grace and admiration. “You look at their careers and think, you did everything. How could you possibly want more? So I think it’s just ingrained in all of us to really not be fully satisfied,” Keys said, referencing Novak Djokovic and Serena Williams, two titans still defined by their insatiable pursuit of excellence.

For Keys, the WTA Finals represent a full-circle moment. Her last appearance came back in 2016, a lifetime ago in tennis years, when she reached back-to-back WTA 1000 finals in Rome and Montreal, only to fall short to Serena Williams and Simona Halep.

In Singapore that same year, she faced Halep again, losing in straight sets in the group stage. A lone victory over Dominika Cibulkova followed before Angelique Kerber ended her campaign, leaving Keys to walk away empty-handed but wiser.

Now, nearly a decade later, she returns not as a contender, but as a champion. With a Grand Slam title finally etched beside her name, the question now is: can Madison Keys rise once more, capture the year-end crown, and etch her legacy among tennis’s modern greats?