
Update, June 8: UFC middleweight title challenger Yoel Romero came in 0.2 pounds over the 185-pound maximum at Friday’s official weigh-in, rendering him ineligible to win the title on Saturday night. Whether the fight will proceed as a non-title matchup or be canceled is still to be determined.
If you want to bring up a polarizing topic in fight circles, just toss the name “CM Punk” out there and stand back as MMA purists lose their shit. After becoming a star pro wrestler in WWE, Punk made his MMA debut at UFC 203 in 2016 and — unsurprisingly — got his ass handed to him by a young, relative unknown named Mickey Gall. That fight had the MMA faithful alternately laughing and shaking their fists at the UFC for its transparent opportunism, with the lesson being that you can’t throw just anybody in there against a trained killer and expect anything good to come out of it.
That was right around when the ambiguous term “UFC caliber” came into popular conversation, as well — meaning a well-rounded fighter who belongs in the sacred octagon, not one who moonlights to cross off an item on their bucket list. Yet if it felt like a mockery to put a 0–0 fighter on a pay-per-view based on cheap name recognition, it was a mockery bound to repeat itself.
And that’s where we’re at heading into UFC 225 Saturday night, because guess who’s back. Everyone’s favorite weekend warrior, CM Punk! To be fair, he’s been training full time since he left WWE, a cram session just to get up to speed. Now 0–1, he will try his hand in the octagon again, this time after packing in 21 months with Duke Roufus in Milwaukee. It’s no accident that he will get his mulligan fight in his hometown of Chicago, which adores him regardless of his inability to defend a rear-naked choke. And it’s no surprise that he ended up on the pay-per-view portion of the card, because the best voyeurs (read: most of the fighting audience) never grow tired of paying for disappointment, especially in the off chance that they’re wrong.
Above all, it’s no shocker that Punk’s opponent is Mike Jackson, a photojournalist-cum-cage-fighter who sports an identical 0–1 record. It’s the perfect fight for each man, and the most mystifyingly compelling no-future redemption fight the UFC has ever booked. In other words, a weird kind of awesome.
Here’s a look at this weekend’s big PPV, starting at the top with a middleweight title fight.

Round 1: Yoel Romero vs. Robert Whittaker II
The middleweight division has been a mess ever since Georges St-Pierre vacated the title just 33 days after taking it from Michael Bisping at UFC 217 in November. In fact, it’s been downright preposterous. Even before that fight went down it was ugly — Bisping took his sweet time to defend the actual title, forcing an interim title contest that Whittaker won by defeating none other than his opponent this weekend, Romero (more on that in a minute). After inheriting the actual title after St-Pierre’s abdication (and having the interim designation lifted), Whittaker was supposed to make his first defense against Luke Rockhold at UFC 221 in February, but a gruesome staph infection on his stomach forced him out.
Romero then stepped in to fight Rockhold on short notice for what can only be described as a second-wave interim title — essentially, a championship trying to keep up with the absurd circumstances. To make things even more absurd, Romero missed weight, thus rendering only one half of the equation (Rockhold) eligible to win that interim title, and turning the UFC’s middleweight crown into a crude X on a drunken pirate’s map. So what happened? Not only did Romero defeat Rockhold in Perth to (re)emerge essentially as the no. 1 contender, he kissed him for good measure, which Rockhold received but reluctantly, as if he was just happy to be rid of a horrible date.
Now we have a bizarrely circumstantial rematch between Romero and Whittaker for — at long last — the undisputed middleweight title. There were some groans that Romero shouldn’t be gifted a title shot after missing weight in his title eliminator, but since it was taken on late notice the UFC didn’t feel the need to punish him. And let’s be honest, to throw another wrench into the system would be enough to make even a casual fight fan’s head explode. The division needs to get rolling again in a direction that everyone can understand.
Romero is 9–1 in the UFC since the 2012 Strikeforce merger, with his only loss coming to Whittaker. He is a Cuban bulldozer who razes any human structure that opts to trade with him. It should also be noted that he’s a little long in the tooth at 41 years old — his time is running out to become a UFC champion, and this is, in all likelihood, his last crack at it.
The real story in this matchup is the 27-year-old Whittaker, who has quietly become the man to beat at 185 pounds through all of the static and change. Not only did he serve up Romero on a platter, he knocked out Ronaldo Souza a little over a year ago when “Jacaré” was a cherished commodity at the top of the middleweight food chain. That was the bout that truly raised some eyebrows and made him a force to be reckoned with.
But the situation isn’t ideal for the man they unofficially call “Bobby Knuckles”: He has already proved himself against Romero, and getting up for the task again can’t be easy. Then again, Whittaker’s mind-set is similar to that of featherweight champion Max Holloway, who — through similarly fated circumstances — was asked to take out pound-for-pound great Jose Aldo not once but twice just to get his own division out of neutral. Holloway came through with flying colors, knocking Aldo out both times late in the third round.
For Whittaker to duplicate his feat with Romero, against whom he won a decision the first time through at UFC 213 last summer, he may need to rip his heart from his chest and hold it up for the Cuban to see. Otherwise, he might find himself getting kissed after a Romero power-bomb, leaving him to wonder how it all got to that in the first place.

Round 2: Rafael dos Anjos vs. Colby Covington
If there was ever a fighter you could call an irredeemable xenophobic troll and get them to wink, it’s Colby Covington — the most hated contender on the circuit. The thing is, he’s fully aware that he’s the sport’s biggest dick; in fact, he embraces it. That’s why he pinned spoilers on his Twitter account for movies like Star Wars: The Last Jedi and Avengers: Infinity War the day they came out, hash-tagging the shit out of each just so that you may accidentally stumble on them and ruin your weekend. For Covington, your anger is like vibranium surging through his body. He once called Brazilian fans a bunch of “filthy animals” after beating Demian Maia down in São Paulo. Colby is that guy. In his mind, he’s the Andy Kaufman of MMA.
What works in his favor is that — as with Punk, but for different reasons — people want to see somebody like that get their ass kicked, and most would happily pay for the privilege. The next one to get the chance is well capable of doing it, too — Rafael dos Anjos, the former lightweight champion and newly crowned Bringer of Justice. Dos Anjos was in line to fight for the welterweight title against Tyron Woodley, but timing (and a Woodley injury) prevented the fight from materializing. Instead, dos Anjos will fight the hated Covington for the interim title, and the winner will (presumably) get Woodley next.
This is a fantastic fight, not just because it matches the paragon of heeldom versus a perfectly mild-mannered baby face like RDA. Covington (13–1, 8–1 in the UFC) is one of those special intrigues who will wrestle an opponent to death, and let his hands go when necessary. He made fighters like Maia and Dong Hyun Kim stare up at the arena lights for long blocks of time. He makes a 15-minute fight feel like 30 and can usually impose his will for every second of the encounter. Worse, he does all this with a smug satisfaction that dares anybody to stop it — or any fan to bellyache about it.
What’s fun about this fight is that dos Anjos — a pressure fighting buzz saw — doesn’t take well to dictation. In fact, he punishes aggression and fills his opponents with second thoughts in real time. It’s easy to imagine Covington changing levels for a takedown and eating an uppercut issued from hell, just as it’s easy to think of dos Anjos winning a scramble, taking Covington’s back, and then making him tap to a standing ovation from the fans who’ve learned to hate Covington in his run toward a title.
The ovation wouldn’t come from the UFC, who has in Covington the kind of self-aware villain that can do something no fighter has done before — that is, sell a pay-per-view involving Woodley. To this point, the current welterweight champion hasn’t exactly been a box office smash. Covington, who has bickered with Woodley on social media and in the media for the past year, is the perfect foil for a champion that could desperately use one. You could forgive the UFC for rooting for the bad guy in this scenario.

Round 3: CM Punk vs. Mike Jackson
It’s never a good omen when you spend the early days of Fight Week in a courtroom battling a lawsuit, but that’s where CM Punk found himself as late as Tuesday afternoon. Luckily he was cleared by a Cook County jury of defamation and invasion of privacy charges that a WWE doctor Christopher Amann brought against him, just in time to exhale, sing “Take Me Out to the Ballgame” at Wrigley Field, cut weight down to 170 pounds, and then proceed to trade punches come Saturday night with some dude who has never followed a script in his life.
This isn’t likely to be a barnburner, or even a memorable encounter, though nobody can deny that it’s very compelling setup. Usually in the fight game, the formula is that we get excited going in, and scoff coming out. The best-case scenario here is that Punk flips the script, making it so that though we may scoff like skeptics going in, we won’t be able to contain our excitement coming out.
It’s a tall order. The intrigue is that the 39-year-old Punk — real name Phil Brooks — could be subjecting himself to a second humiliating showing under the UFC banner. The X-factor is the great unknown: Nobody knows if Punk has any “real fight” ability or not. That’s a weird premise for drama in a professional cage match.
The truth is, we didn’t get to see what Punk has been working on behind closed doors the first time. He went right at Gall in his first fight and ended up getting taken down with relative ease. The next thing you knew, it was over. I have a feeling that it won’t take much for Punk to inspire some awe in a fight carrying such low expectations. If he can touch up Jackson a bit on the feet, maybe get some elbows in on the clinch, perhaps score a takedown and, who knows, exact some ground and pound … well, that would have a good many people slapping fives in Chicago.
If he loses to Jackson, it might be time to consider a return to the WWE. Or, you know — make MMA a hobby and not a job.

Round 4: Holly Holm vs. Megan Anderson
Nobody loses as inconsequentially as Holly Holm, who is now 1–4 since knocking out Ronda Rousey at UFC 193 and yet is still right there in contention for another title shot. It helps that she and her opponent this weekend — newcomer Megan Anderson — are literally the only two contenders in the recently established women’s featherweight division. Unless the UFC can arrange a superfight between bantamweight champ Amanda Nunes and the current 145-pound champ, Cris Cyborg, the winner here is next in line for a shot.
Which of course fills this fight in existential dread. Winning a crossroads bout just to go fight Cyborg is like the Denver Nuggets fighting desperately for a spot in the NBA playoffs just so they can get slaughtered by the Warriors. It’s the kind of triumph that comes with a cruel sentence.
All that aside, the former boxing champ Holm is in dire need of a victory just to stay relevant, regardless of her indelible feats. It’s been a strange slide for Holm, who was winning her fight with Miesha Tate before getting choked out in the fifth round, and who lost to Germaine de Randamie controversially less than a year later. The one thing we know about Holm is that she’s capable of ending a fight at any time. Her head kicks of Rousey and Bethe Correia remain in heavy rotation on UFC highlight reels.
For Anderson, who won the Invicta FC 145-pound championship in her last fight against Charmaine Tweet, it’s a chance to hit the ground running in the UFC. Her last four victories have all come via stoppages. Given that she wants to make a statement and declare herself ready for Cyborg, and Holm is hungry to prove she’s still got it, this has Fight of the Night candidate written all over it.
Round 5: Best of the Rest
- Andrei Arlovski vs. Tai Tuivasa: The UFC’s heavyweight division is in a state of flux right now, with some of the brand names getting old and some of the young guns packing heat. This is one of those changing-of-the-guard fights as Australia’s Tai Tuivasa — a Mark Hunt protégé who has finished all seven guys he’s faced in the cage professionally — gets a chance to take target practice on a legend in Arlovski. Arlovski is fighting in his adopted home of Chicago and will have the fans on his side, but Tuivasa has the power to knock his jaw into the cheap seats.
- Alistair Overeem vs. Curtis Blaydes: Ditto everything mentioned in the previous fight, only it’s the Chicago native Curtis Blaydes who’s ready to snatch the baton from a perennial top-five contender. Neither fighter here is a fan of ending up on the prelims, not with CM Punk fighting on the main card ahead of them. But disgruntled fighters have a way of delivering. The wrestler Blaydes is coming off the biggest win of his career at UFC 221 when he scored a decision over Mark Hunt. A knockout of Overeem would rejigger the heavyweight division and deliver Blaydes towards the top of the rubble.
- Rashad Evans vs. Anthony Smith: If there’s ever been a fighter more desperate to get off the schneid than Evans, I’d like to hear about them. The former light heavyweight champion hasn’t won a bout since 2013, not even against clearance-bin fighters booked to return him glory. This time, Evans is going against Anthony Smith, a toe-to-toe slasher whose chin is about as tough as they come. He’s also known to dole out some punishment, too, having knocked out Hector Lombard nine months ago in Pittsburgh. This has the feel of a sad fight, but if anybody can land the Hail Mary to turn things around, it’s the heavy-handed Evans. To do that, he’ll need to something he’s been reluctant to do in his last few fights. That is, pull the trigger.