Generations rarely collide without fireworks, and women’s boxing has found itself on the brink of one of its most explosive chapters yet. On one side is Claressa Shields, a two-time Olympic gold medalist turned undisputed middleweight champion, whose climb from Flint, Michigan, to boxing superstardom has made her a modern face of the sport. On the other stands Laila Ali, the undefeated daughter of the legendary Muhammad Ali, who, despite retiring in 2007, still casts a shadow long enough to spark debates about greatness every time her name is mentioned. For years, whispers of a super fight between Shields—who headlines a bout on July 26 at Detroit’s Little Caesars Arena—and Ali, who has yet to confirm any return date, have simmered.

The latest flashpoint came not in the ring, but on Instagram, where the self-proclaimed GWOAT was seen laughing hysterically at a new fan-given nickname—“Y’all, listen—somebody on here called me ‘YN-ressa’ (laughs hysterically). Hey, you know, there’s a couple of people mad that I called out Laila, and they were like, ‘Laila, you better not come out and fight that YN’ (laughs again). Like, why are y’all so mad at me?” Shields joked in a video reposted by LiveBitez. Her playful jab comes as reports confirm that her camp has finally matched the jaw-dropping $15 million purse Ali once demanded, a figure originally revealed by Athlon Sports’ Prince Horton as the barrier to bringing the 46-year-old back to the ring.

This rivalry, however, isn’t some manufactured sideshow. Its roots trace back to 2019, when Ali, speaking to DJ Envy on The Breakfast Club, casually mused, “Money right, Laila there every night… I don’t think there’s anyone there for me that would give me a good challenge.” Though not aimed directly at Shields, the Michigan native took offense and told the same program shortly after, “Until that day I’ve never disrespected Laila Ali… so when I heard her say that, is she saying I don’t know how to box? If you come out of retirement, I’ll smoke you.”

Since then, tensions only escalated—Ali doubling down on First Take by calling Shields’ “mouth” the spark for her interest, Shields telling ESPN’s Myron Medcalf she’d “wear her down and punch her to the body until she quits,” and both women relitigating their feud on Andre Ward’s All the Smoke Fight Podcast.

Laila Ali’s $20 million demand sparks a fiery one-liner from Claressa Shields

The chatter reignited during the Katie Taylor vs. Amanda Serrano trilogy event, where the 47-year-old Ali made waves with a bold stance on a comeback. “The rumor that I heard is that I said, ‘Unless somebody has $15-$20 million, don’t even call me about this,’” Ali said when pressed about a possible bout with Shields. When a reporter floated the idea that His Excellency Turki Alalshikh might bankroll such a fight, the retired champion didn’t budge, adding, “Unless somebody calls me and says they have it, we’re not even gonna have a conversation.” Though she admitted she doesn’t plan to return, Ali conceded that “if someone offers me that kind of money, I would actually have to think about it.”

The comments quickly sparked debate across social media, with one fan insisting Shields could easily defeat Ali today but that a prime-vs.-prime version of the matchup would favor the daughter of “The Greatest.” Shields wasted no time answering that speculation, firing back on Instagram with a concise warning: “Laila can’t beat me in no era!” It was a blunt reminder that the 16-0 champion sees no version of this hypothetical clash where Ali comes out on top.

Still, the self-proclaimed GWOAT insists that a bout with Ali—retired or not—would eclipse any other fight in women’s boxing, even in exhibition form. Appearing on the Art of Ward podcast, she doubled down: “Me fighting her right now is still the biggest fight in women’s boxing… You got all the Amanda Serranos and Katie Taylors, but Claressa Shields vs. Laila Ali—even in an exhibition—is still the biggest fight in the world for women’s boxing.” Whether the right checkbook makes that claim a reality remains to be seen, but with Ali setting her price and Shields already issuing challenges, the hype machine shows no signs of slowing.