Opinion
8-Match Tag: The Ballad of Shawn Michaels vs. The Undertaker
I’m Sean. You’re not. Welcome back to 8-Match Tag, my personal compendium of short-and-sweet personal playlists for new and well-read wrestling fans alike from the archives of WWE Network.
Let’s now journey just barely more than 20 years into the past and observe the eight essential milestones comprising a legendary feud that stands up today as a touchstone defining the finest hours in the careers of two storied icons. This cyclical saga’s sun dawns and sets with a show-stopping, controversial supernova of charisma holding an ultimately relentless rival’s destiny in the palm of his hand. The battles falling between the catalyst and culmination of their conflict brought out nothing less than each man’s best, despite nine years passing without their paths crossing and a combined 15 years separating the trailblazing first salvos and bittersweet punctuation of their story.
If I somehow haven’t made this evident, we now chronicle one of my all-time favorite arcs ever to emanate from any era or company in professional wrestling history. This is the ballad of Shawn Michaels and The Undertaker.
WWF SUMMERSLAM – August 3, 1997
WWF CHAMPIONSHIP MATCH
The Undertaker © vs. Bret “The Hitman” Hart, w/ special guest referee Shawn Michaels
As the now-former World Wrestling Federation approached SummerSlam in August 1997, few could have foreseen back-to-back marquee matches altering the path for the company’s ensuing 20 years atop the professional wrestling landscape.
In one, a catastrophically botched Owen Hart piledriver nearly crippled “Stone Cold” Steve Austin’s and set the stage for the Texas Rattlesnake’s pivotal 1999 neck surgery and the eventual onset of spinal stenosis which would combine to bring the curtain down on the career of wrestling history’s single most popular, impactful and profitable star.
In another, WWF Champion the Undertaker’s second reign with the belt met the challenge of Bret “The Hitman” Hart. Since 1996, Hart’s storylines had blurred backstage acrimony and frustration with a bizarre heel turn that saw Bret booed without mercy in the United States and heralded as practically a conquering national hero in his native Canada. Michaels often dove without hesitation into the center of Hart’s all-too-real professional frustrations and offering an increasingly loathsome character foil, but on this night, he would shape all three men’s oncoming paths. After extensive antagonization, the Heartbreak Kid stepped up as special guest referee just as Hart had declared that, should he fail to wrest the WWF Championship from the Deadman, America would see the last of the Excellence of Execution.
There was just one additional catch: HBK called Hart’s bet by announcing that he too would never again wrestle on U.S. soil if he showed blatant favoritism to the champion.
It truly is a crying shame Hart worked so relatively few major matches opposite the Undertaker. Both displayed a consummate commitment to hard-hitting, physically grueling matches executed to closely resemble a believable donnybrook – yes, even the one portraying a wrestling zombie. This was absolutely no exception. The pair demanded minimal suspension of disbelief. Their pacing rarely allowed the tension to waver for a second. Best of all, the match’s entire narrative wove Michaels’ stakes seamlessly into Hart and the Undertaker’s own, advancing several stories concurrently without one ever seeming poised to overshadow the others. In the end, Hart’s animosity toward Michaels boiled over in the form of a single finely aimed loogie landed squarely in HBK’s face. Michaels offered a receipt in the form of a swing-for-the-fences blast with the steel chair he had only just confiscated from the Hitman – a blow which jacked the Undertaker’s skull when Hart deftly slipped out of the way. Bret went for the cover. His arch-enemy reluctantly counted the fall.
The fallout is the stuff of legend, almost enough so to overshadow one of the most timelessly watchable main events in the company’s history. Hart’s fifth and final reign as WWF Champion would come to an ignominious end three months later against Michaels himself at Survivor Series in the sea-changing Montreal Screwjob, after which the Hitman would end his storied career with a WCW tenure lasting from 1997 until a tragic concussion forced him into retirement in 2000.
As for Michaels? Before holding the WWF Championship for a third and final time, he would embark on a collision course that would eventually lead him through Hell and back.
WWF IN YOUR HOUSE: GROUND ZERO – September 7, 1997
Shawn Michaels vs. The Undertaker
“Shawn Michaels, you’re going to have to look me in the eyes, and you are going to have to pay for your crimes,” the Undertaker prophesied in the wake of SummerSlam.
Unsurprisingly, Michaels wasn’t exactly impressed.
“You’re either with me or against me. Take your pick,” HBK declared. “The Undertaker is going down in a blaze of fire.”
Michaels boldly defined that line in the sand by proudly raining down two thunderous blasts with a steel chair onto the Deadman’s cranium on “Monday Night Raw”, both of which made the assault at SummerSlam look like tee ball batting practice. Naturally, the Undertaker sat bolt-upright and seared a hole in Michaels and HBK’s two newly joined D-Generation X companions Hunter Hearst Helmsley and Chyna with his cold, dark eyes. Appropriately, Michaels and the Undertaker were then tabbed to close In Your House: Ground Zero – a main event somewhat ironically preceded by Bret Hart defending his newly won WWF Championship against The Patriot, match inspired by Michaels previously costing Hart a televised match against the red, white and blue contender.
The Undertaker was a gigantic, heavy-hitting mauler with a relentlessly methodical offensive approach and uncanny agility that seemed fascinatingly misplaced on a man standing 6 feet 10 inches tall and weighing in over 300 pounds. Michaels’ electrifying personality and brash bravado complimented legendary high-flying assaults and no shortage of technical wrestling proficiency – not entirely unlike Hart in many ways except his once-notorious toxic attitude. In hindsight, it should have come as no surprise that these two well-traveled veterans would display instantaneous chemistry far outstripping the theoretical limitations of their differences. Whereas Hart tried to scientifically dissect the Undertaker, Michaels opted to remain abusive and elusive. When he finally had nowhere left to run, HBK proceeded to sell a brutal hammering at the Deadman’s hands.
This was no mindless brawl. It was the prelude to two masters of in-ring psychology diving a level deeper into their bags of tricks. Of the eight milestone matches involving these two men, it baffles me how rarely this first significant confrontation falls under the radar. Before a conclusion marred by interference, Michaels and the Undertaker had made their point: we hadn’t seen anything close to the best of either of them yet. This encounter was violent, wild and more than entertaining enough by a solid margin to top Ground Zero’s bill without a single championship on the line. Still, it left unfinished business neither man could abide. Desperate times called for desperate, unheard-of measures.
WWF IN YOUR HOUSE: BAD BLOOD – October 5, 1997
HELL IN A CELL
Shawn Michaels vs. The Undertaker
A mere ring could not contain the volcanic animosity between these two. When last they met in a one-on-one confrontation, their fight culminated in the WWF locker room spilling onto the arena floor to separate the Undertaker from Michaels, Helmsley and Chyna after an inconclusive no-contest. For their efforts, the assembled would-be peacemakers were wiped out by the Undertaker leaping cleanly over the top rope and flattening them all like bowling pins decked out in late-1990s street clothes. Finality would call for something unprecedented in the annals of the World Wrestling Federation.
It’s one of those moments wrestling fans of nearly any age in the late 90s will never forget. Some were closely familiar with War Games, a covered chain-link cage covering two rings and entrapping rival teams of four or five men who entered one at a time. This was an evolved beast, a mammoth roofed enclosure lowered over both the ring itself and most of the perimeter outside it. The structure’s objective? Seal two fierce enemies locked at their breaking points inside and leave no means for any third party to enter the fray.
Jim Ross, one of the company’s most esteemed announcers, often referred to it as “the Devil’s Playground” with reverent hyperbole. In the beginning, it was simply known as Hell in a Cell.
Before WWE watered down the gimmick into an annual pay-per-view event that hasn’t always featured feuds suited to its violent legacy, Hell in a Cell was the nuclear option. When disdain outlived wrestling’s most torturous stipulations (cage matches, bullrope matches, street fights, etc.) and left two enemies with no other path for conclusively settling a grudge…Hell would await. That was the bar set by Michaels and the Undertaker in St. Louis that evening. Without Helmsley, Chyna or “Ravishing” Rick Rude by his side and a remorseless reaper in black standing across the ring from him, Michaels struggled to survive while the crowd relished seeing the Deadman finally beat vengeful blood from HBK without realistically expecting an interruption. The Showstopper sold a beating for the ages while the Undertaker himself got over Michaels’ own tide-turning offense and experienced cunning to maintain the war’s unpredictability, especially when Shawn eventually finagled an escape from the titanic torture chamber.
Naturally, if a man can get out…a demon could find its way inside. With the Undertaker poised to impact a dent shaped like Michaels’ cranium in the mat with a Tombstone, the lights went black. Flames erupted. The Deadman’s nemesis and former manager Paul Bearer strode down the aisle with a Goliath clad head-to-toe in red and black behind him. The beast tore the door from its hinges, stood face-to-face with the Undertaker and promptly destroyed him with a Tombstone of his own, leaving Michaels to limply cover him for a three-count. Kane, the Undertaker’s presumed-dead younger brother, had come to settle old accounts.
For the time being, the book had been closed on HBK. However, it wouldn’t take long for one consuming feud to entangle itself with another.
WWF ROYAL RUMBLE – January 18, 1998
WWF CHAMPIONSHIP CASKET MATCH
Shawn Michaels © vs. The Undertaker
By the 1998 Royal Rumble, circumstance had upped this seemingly ceaseless rivalry’s ante an additional order of magnitude. In an instant destined to live in infamy amidst the WWF Championship’s hallowed history, Michaels had controversially stolen one last reign atop the mountain from Bret Hart at Survivor Series the previous November. In the meantime, the Undertaker had seemingly made amends with his brother after months of being challenged to a face-off apparently decades in the making. That left the Deadman seemingly free and clear to pursue a third WWF Championship in another specialized encounter he had previously pioneered: a casket match.
In order to win, one man would have to dump the other into an oversized casket situated at ringside and close the lid. No count-out, disqualification, pinfall or submission would otherwise end the match. Keep that in mind. One day, I just might count down my favorite occasions during which that loophole bit the Undertaker squarely on his cold, dead ass.
While a satisfyingly and typically brutal affair between two men seemingly incapable of working a patently unwatchable match together, this main-event spectacle bears unfortunate historical significance beyond being the final clash between Michaels and the Undertaker for nine years. At one point, Michaels took a seemingly routine spill over the top rope and slammed his back against the perpendicular edge where one of the casket’s sides met its lid. On an initial viewing without context, the impact doesn’t appear terribly traumatic – painful, but one wouldn’t think it anything to write home about.
Beneath the surface, that spot herniated two discs in Shawn’s back and completely crushed another. Despite retaining his championship when Kane and Bearer emerged to seal the Undertaker inside the casket and set it ablaze after the match, Shawn Michaels would not wrestle a one-on-one match again until dropping the belt to “Stone Cold” Steve Austin at WrestleMania XIV months later. Putting Austin over would give way to a four-year retirement and the universally accepted belief that HBK would never set foot as an active competitor inside a ring again.
WWE ROYAL RUMBLE – January 28, 2007
THE ROYAL RUMBLE MATCH FINALE
Fate was not yet finished with this tale. Not by a long shot.
I refuse to pretend the closing triad of matches finishing this feud once and for all were already planned three years before the first of them took place. Every so often, things simply fall into order that way. In 2002, Shawn Michaels returned to WWE a drastically changed, redeemed man. Over the course of five intervening years, he rode what was to be a one-off career finale against former friend and DX running mate Triple H at SummerSlam into five years of stellar matches that surpassed even some of his most thrilling matches of the 90s as a standard-bearer for the company, including a brief reign as World Heavyweight Champion and an unforgettable WrestleMania XX main event war with Triple H and Chris Benoit. During that same time, the Undertaker returned to his ominous “Deadman” persona at WrestleMania XX after several years as a no-nonsense biker with a penchant for beating down anyone who dared slide a toe into his yard.
As the field dwindled in the 2007 Royal Rumble match with a punched ticket to a WrestleMania 23 championship match hanging in the balance, time stood still. The bloodied Undertaker sat up. An exhausted, rubber-legged Michaels, appropriately clad once more in the green and black of D-Generation X, kipped up to his feet. For the first time in almost 10 years, they locked eyes across an empty ring – two defiant, battle-hardened Texans renewing their war before a suddenly unglued San Antonio crowd. For seven more minutes of gapless action, both turned back the clock to 1997 and delivered quite possibly the most thrilling Royal Rumble conclusion the match has ever seen. Each narrowly averted elimination over the top rope several times. The Undertaker flattened Michaels with a downright sadistic chokeslam. HBK appeared to turn the tide with pinpoint-perfect Sweet Chin Music. As he found his feet and moved in for one more superkick to seal a record-setting third Royal Rumble victory, the Undertaker ducked under and ousted Michaels for his first.
In Detroit at WrestleMania 23, it was Michaels who would close out the Showcase of the Immortals in a fantastic WWE Championship match against John Cena. Earlier in the evening, the Undertaker would take the World Heavyweight Championship from Batista in an astounding match whose quality was purportedly elevated by both men resenting a perceived backseat taken to Cena and Michaels, complete with Batista allegedly screaming “Let’s see them top that!” as he returned backstage. However, Michaels and the Undertaker perhaps had not yet realized what their performance in January had already insinuated: their story wasn’t finished after all.
WRESTLEMANIA 25 – April 5, 2009
Shawn Michaels vs. The Undertaker
As the road to WrestleMania’s diamond-anniversary celebration drew nearer to its ultimate destination in Houston, HBK walked tall with the backbone of a rejuvenated man with a new-found mission after winning his freedom from a demoralizing period of indentured servitude to John “Bradshaw” Layfield. In the midst of the personal identity crisis that plagued him as the well-heeled Texan held Michaels’ financial soul in the palm of his hand, he was once briefly confronted by his greatest adversary with a succinct, pointed message: “It is sometimes hell trying to get to Heaven.”
With his freedom restored, Michaels trained his gaze toward a WrestleMania homecoming with a single point to prove: he was still the Showstopper…the icon…the headliner…the quintessential main event. As far as he was concerned, there was but one way to leave no doubt. Once more, he would have to do what many declared “impossible” and etch his name upon unbroken ground.
As far he was concerned, he was destined to bury the Undertaker’s unparalleled undefeated WrestleMania record. He would forever be acknowledged as the “1” in “16-1.” A legion of champions, giants and legends had fallen at the Deadman’s feet on the Grandest Stage of Them All. However, the Phenom had never bested Mr. WrestleMania where his unbridled, unrivaled talent had always shone brightest.
In the weeks leading to WrestleMania 25, Michaels reminded the Undertaker time and again that his ever-present psychological warfare had never worn down a fighting spirit or warrior’s will quite like his own. Instead, Michaels repeatedly laid the Deadman flat on his back with his most devastating blow, Sweet Chin Music. If veteran spectators hadn’t known better, we could have sworn HBK had accomplished the unthinkable and planted his own seed of doubt within the Undertaker’s head.
“That might have been the one to end it on,” Michaels would tell a WWE interviewer years later. “If that wasn’t perfect, that’s as close as you can get.”
After over 30 minutes of drama and impeccably paced storytelling by which all headlining WrestleMania bouts henceforth should be measured, Shawn Michaels and the Undertaker had declared they were no longer two proud men vying for one-another’s professional respect. The years had meticulously shaped them into two consummate artists who had risen above and beyond having each earned such respective admiration. Triple H and Randy Orton faced the unenviable mountain that year of having to follow a match for the ages. Both have since conceded, the it was a fool’s errand. Without a single wasted motion, Michaels and the Undertaker imbued every spot and sequence with a deliberate structure. One expression and mannerism after another shaded in each man’s path toward victory and defeat.
This was wrestling artistry. However, it was not how this story was fated to end.
WRESTLEMANIA 26 – March 28, 2010
CAREER VERSUS STREAK
Shawn Michaels vs. The Undertaker
You know something? Absolutely nothing I could conceivably write here would encompass the ascent from WrestleMania 25’s undeniable masterpiece to this poignant chapter better than this. I tried for hours.
When WWE gives enough of a damn, nobody builds a big-fight feel quite like them.
Two years earlier, Shawn Michaels penned the final in-ring WWE chapter of his idol, mentor and friend, “Nature Boy” Ric Flair. It ended with Flair rising to his feet, dukes up, demanding that HBK hold nothing back and finish him as only the Showstopper could. There is a poetic parallel to Michaels, a weathered and crumpled man, pulling himself up the Undertaker’s body to slap the Deadman across the face and deliver his opponent’s signature throat-slice taunt. That Phoenix evening did not surpass their furor from a year prior, despite being a no-disqualification affair. If these two men were to share a ring this way only one last time, they were nevertheless determined to leave an unforgettable impression.
Oh, by the way? This time, they went on last.
Still…the all-encompassing end of an era would have to wait another two years.
WRESTLEMANIA 28 – April 1, 2012
“END OF AN ERA” HELL IN A CELL MATCH
Triple H vs. The Undertaker
Special Guest Referee – Shawn Michaels
Two years had passed. At the very WrestleMania which celebrated Shawn Michaels’ induction into the WWE Hall of Fame in 2011, his closest friend met his indomitable rival for the second time at the Showcase of the Immortals. Triple H had declared their match a meeting to determine who was truly WWE’s “last outlaw” of a generation rapidly aging out of professional wrestling’s rigors. In some sense, it was obviously also a matter of avenging the fall of his compatriot’s career a year prior. He battered and abused the Deadman to such a horrendous degree that, despite succumbing to a deftly timed Hell’s Gate choke sunk in by the Undertaker out of instinct and desperation, it was only the Cerebral Assassin who walked out under his own power.
It took weeks on end of assaults on the Game’s pride for the Undertaker to finally receive the rematch he demanded. He could not abide the image of his limp body being carted from the ring to serve as his enduring legacy. Time and again, Triple H turned to his duty as a newly minted WWE executive to justify his refusal to potentially cripple WWE’s most valuable competitor. When at last he conceded, he invoked a stipulation threaded deeply throughout both men’s careers, the only way to bring closure to this journey: Hell in a Cell.
Fittingly, there was a man who had met both the Undertaker and Triple H inside the sadistic cage and lived to fighter another day. His own career had been defined by each competitor. He had been there from the beginning of this acrimony which had united all three indelibly in WWE history.
Shawn Michaels would be there at the end.
“Remember when I told you Shawn was better than you?” the Undertaker said as he stood face-to-face with the King of Kings, adding a pregnant pause. “He is.”
However, the Deadman also issued a warning to Michaels, once perhaps seasoned with memories of how their war had begun: if he compromised the purity of the match’s decision, he would truly end the Heartbreak Kid once and for all.
That isn’t to say Triple H wouldn’t attempt to turn the tables that evening in Miami. He rained down unholy, bone-breaking violence upon the Undertaker and demanded that HBK stop the match. To his credit, Michaels resisted…right up until he seemingly separated the Undertaker from his senses with Sweet Chin Music and scurried into the ropes as Triple H failed to get a decisive three-count. The battle waged on until a spent Triple H leaned into a turnbuckle and defiantly saluted the Undertaker with a classic D-Generation X chop to his crotch, saying without words, “You’ll have to finish me yourself.”
He did. In the end, it was the image Shawn Michaels and the Undertaker, side by side, helping Triple H to the back which will always punctuate this end to an era.
There was no feud like it before. There will be none like it again. Thank you for joining me. If you have any comments or would like to point out some error, feel free to follow @ComerCodex on Twitter and let me know. Until next week, it’s time to tag out. I’m Sean. You’re not. Never dull your colors for someone else’s canvas.
About Chairshot Radio Network
Launched in 2017, the Chairshot Radio Network presents you with the best in sports, entertainment, and sports entertainment. Wrestling and wrestling crossover podcasts + the most interesting content + the most engaging hosts = the most entertaining podcasts you’ll find!
MONDAY - Bandwagon Nerds (entertainment & popular culture)
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CHAIRSHOT RADIO NETWORK PODCAST SPECIALS
Attitude Of Aggression Podcast & The Big Five Project (chronologically exploring WWE's PPV/PLE history)
TheChairshot.com PRESENTS...IMMEDIATE POST WWE PLE REACTIONS w/ DJ(Mindless), Tunney(DWI) & Friends
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Classic POD is WAR
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Opinion
DeMarco: Eric Bischoff, Vince Russo, or Jim Cornette?
Greg DeMarco evaluates a $10 million dollar question (literally) – who would you choose if you were starting a new wrestling company?
Greg DeMarco evaluates a $10 million dollar question (literally) – who would you choose if you were starting a new wrestling company?
Social media has flipped the script on pro wrestling. The fans have more power than ever before—booking is done in real time, buzz is built or buried in seconds, and no one waits until Monday to cut a promo anymore.
Social media is also a place where ideas are shared and discussion takes place. The basis for this article was a question posted on social media, using this image:
It’s the Ten Million Dollar Question: If you are handed $10 million to start a wrestling company, and you have to pick one of the following as your partner, who do you pick? Eric Bischoff, Vince Russo, or Jim Cornette.
Ten Million Dollars?
Ten million dollars sounds like a lot—until you start pricing out weekly production, talent contracts, live event logistics, licensing, digital, and TV. That money will go fast when you realize you’re competing with billion-dollar conglomerates that can lose money just to win the culture war. To truly break through in today’s wrestling economy, $10 million is your entry fee, not your war chest.
You do have options, such as Roku TV (similar to the NWA), YouTube, and more. This should ABSOLUTELY factor into your decision–distribution is key. And all three options do have some connection, and that needs to be considered.
You already know the options…
You’re reading this article, so you already know all about Eric Bischoff, Vince Russo, and Jim Cornette.
Eric Bischoff broke all the rules—and made it work. He launched Monday Nitro, flipped the industry upside down with the nWo, and forced Vince McMahon to innovate. Bischoff turned WCW into a legit number one brand and changed the entire TV presentation of wrestling forever. Without him, do we have the Attitude Era? There’s no way to be certain.
Vince Russo brought the chaos—and a whole lot of ratings. He gave us Crash TV, blurred the lines between fiction and reality, and wasn’t afraid to throw the whole format into a blender. While the long-term storytelling often suffered, the shock factor he brought drove eyeballs and made every segment feel like “can’t miss” television. But you can argue that, without Eric Bischoff, there’s no Vince Russo.
Jim Cornette is wrestling tradition personified. He’s protected the business with his life, shaped generations of talent behind the scenes, and built up territories when no one else could. Cornette’s strength lies in his psychology, heat-building, and his unapologetic belief in what wrestling should be—even when the industry moves past it. Does that play if you’re starting a brand new company in 2025? In my opinion, the jury is still out.
But who do you choose?
To be fair, you can’t just pick someone and go. You need to pick someone who aligns with your vision.
- If you’re trying to focus on “old school” and nostalgia, Jim Cornette is your guy.
- If you plan to build on shock value, your product going viral, and outlandish reactions, you pick Vince Russo.
- If you think distribution is important, and need to get your product out there, you choose Eric Bischoff.
For me? I am a business guy. It’s called “the wrestling business,” and your $10 million investment needs to see a return.
I choose Eric Bischoff.
Many of you will scoff at this, thinking Jim Cornette was the right choice. He has a brilliant mind, and he has a following to help get you started. Hell, its enough for me to second-guess myself. Cornette is a close second. Vince Russo? Not a fan in this scenario.
But my perspective is different. I am a wresting promoter–I book and promote successful wrestling events. Our biggest weakness? Distribution. Among the three options, Eric Bischoff is far stronger.
How do you leverage Eric Bischoff?
Remember how the table was set – you’re given $10 million dollars to start a wrestling company. THAT is the hook. To me, that sounds like two things: a wrestling promotion AND a reality show. Even if the wrestling portion is on a streaming platform, or our own distribution like YouTube–the behind the scenes content is what Eric can start shopping. That can give us more resources in terms of budget and production. He also has the connection to Conrad Thompson, which helps with the online community.
If Bischoff gets us a distribution deal, even if it’s for the reality show portion, we have more budget for talent. Two people I can hire? Jim Cornette and Vince Russo. They are reality show GOLD.
Do I have to pay Eric Bischoff? Sure, but he’s not a “salary guy.” You want to motivate Eric Bischoff to perform, appeal to his competitive side. Give him a piece of the business–when the business grows, so does his piece. That’s one of the biggest advantages to having the former head of WCW.
Welcome to the team, Eric! Now let’s to get ourselves a deal!
About Chairshot Radio Network
Launched in 2017, the Chairshot Radio Network presents you with the best in sports, entertainment, and sports entertainment. Wrestling and wrestling crossover podcasts + the most interesting content + the most engaging hosts = the most entertaining podcasts you’ll find!
MONDAY - Bandwagon Nerds (entertainment & popular culture)
TUESDAY - Musical Chairs (music) / Hockey Talk (NHL)
WEDNESDAY - The Greg DeMarco Show (wrestling)
THURSDAY - Keeping the news ridiculous... The Oddity / Chairshot NFL (NFL)
FRIDAY - DWI Podcast (Drunk Wrestling Intellect)
SATURDAY - The Mindless Wrestling Podcast
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CHAIRSHOT RADIO NETWORK PODCAST SPECIALS
Attitude Of Aggression Podcast & The Big Five Project (chronologically exploring WWE's PPV/PLE history)
TheChairshot.com PRESENTS...IMMEDIATE POST WWE PLE REACTIONS w/ DJ(Mindless), Tunney(DWI) & Friends
Patrick O'Dowd's 5X5
Classic POD is WAR
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Let us know what you think on social media @ChairshotMedia and always remember to use the hashtag #UseYourHead!
Opinion
Greg DeMarco’s WWE SummerSlam 2025 Preview, Betting Odds, & Predictions
Are you ready for WWE SummerSlam? Greg DeMarco makes sure are with his official preview & predictions!
Are you ready for WWE SummerSlam? Greg DeMarco makes sure are with his official preview & predictions!
August 2–3, 2025 • MetLife Stadium
WWE is turning SummerSlam into the biggest blockbuster of the summer with a two‑night extravaganza, packing in title bouts, and celebrity surprise appearances. Let’s dive into the matches, the action that led us here, and the betting lines that tell us who the bookies think bets on.
And of course, the pièce de résistance, my predictions done in true form: Who Should Win? Who Will Win?
And as an added bonus, PC Tunney has sent along his picks, which will be included with each match!
WWE SummerSlam 2025 – Night 1 – Saturday, August 2
World Heavyweight Championship – CM Punk vs. Gunther (c)
Odds: CM Punk (−180), Gunther (+140)
Punk is favored at about a 64% win probability
Punk earned his shot in a gauntlet match, but remember that he came in last to beat a man in Bron Breakker who came in first. Regardless, the tension has been simmering ever since. Gunther’s technical dominance will test Punk’s recklessness, making this a high-stakes and high strikes match. Expect close calls, but if Punk pulls this off, he reestablishes himself at the very top of WWE’s hierarchy (although he doesn’t need it).
- Who Should Win: Gunther
- Who Will Win: Gunther
Look, I know CM Punk is the sentimental pick to win, but Gunther NEEDS to win here. Otherwise, what is he? Gunther is the type of wrestler whose character thrives on wins and losses, whereas CM Punk is a made guy.
PC Tunney’s pick: “CM Punk – If Seth isn’t hurt we likely see a cash in. I’ll stick with he’s hurt and Punk captures gold.”
Roman Reigns & Jey Uso vs. Bron Breakker & Bronson Reed
Odds: Reigns & Uso (−1500), Breakker & Reed (+600)
Roman & Jey are favored at about a 94% win probability
The Bloodline team is an iron-clad force, backed by legacy and brutal efficiency. Breakker and Reed bring raw power and youthful fury, aiming to shock the world. This will hinge on teamwork vs. dominance—do the underdogs coordinate enough to upset the odds? The wildcard in all of this is the WWE’s efforts to build Heyman’s duo, and establish Bron Breakker as a leader, and a star for the new generation. Does that swing the booking? I think it might.
- Who Should Win: Roman Reigns & Jey Uso
- Who Will Win: Bron Breakker & Bronson Reed
Given the betting odds, it might actually be worth dropping a few bucks on this one (I won’t). I don’t think Seth Rollins appears here, but might we see a new member? I think we could. As far as my pick of Breakker & Reed, I’ll go a step further: Bron Breakker pins Roman Reigns. It won’t be clean, but it’ll be forever etched in history.
PC Tunney’s pick: “Roman & Jey – I don’t see Roman losing much.”
Randy Orton & Jelly Roll vs. Drew McIntyre & Logan Paul
Odds: Orton & Jelly Roll (−500), McIntyre & Paul (+300)
Randy Orton & Jelly Roll are favored at about an 83% win probability
Jelly Roll’s wrestling debut has added real unpredictability, while Orton’s veteran savvy balances McIntyre’s muscle and Paul’s sheen. Expect social‑media chaos with a strong element of violencem This match plays to spectacle far more than to wrestling acumen.
- Who Should Win: Randy Orton & Jelly Roll
- Who Will Win: Randy Orton & Jelly Roll
Don’t overthink this one. Play it safe, go with the babyface celebrity.
PC Tunney’s pick: Orton & Jelly Roll – RK… Roll
WWE Women’s Championship – Tiffany Stratton (c) vs. Jade Cargill
Odds: Jade Cargill (−600), Tiffany Stratton (+350)
Jade is favored at about an 86% win probability
Cargill has steamrolled challengers on her way to this pinnacle moment, while Stratton has proven she can hang with the elite (get it?). Will Stratton’s athleticism and swagger crack Cargill’s aura—or will Jade’s debutante dominance silence the critics?
- Who Should Win: Tiffany Stratton
- Who Will Win: Tiffany Stratton
I’m probably stupid, but I don’t think we’re done with Tiffany Stratton as WWE Women’s Champion just yet. Maybe Bianca Belair costs Jade, maybe it’s someone else.
Actually, I’m positive I’m wrong.
PC Tunney’s pick: Jade Cargill – Time to see what Jade’s got!
See, even Tunney knows that I’m wrong!
The Judgment Day (Raquel Rodriguez & Roxanne Perez) (c) vs. Charlotte Flair & Alexa Bliss – WWE Women’s Tag Team Championship
Odds: Charlotte Flair & Alexa Bliss (–400), Judgment Day (+400)
Charlotte & Alexa are an 88% favorite to win here
Rodriguez and Perez have held the titles well through their title defenses, but Charlotte and Alexa bring star power, chemistry and a storyline deeply rooted in reluctant alliances. If Flair & Bliss click at the right moment, they could steamroll Judgment Day’s dominance. But if the champions have hidden synergy? This could be their breakout moment.
- Who Should Win: Roxanne Perez & Raquel Rodriguez
- Who Will Win: Charlotte Flair & Alexa Bliss
It makes WAY more sense for Roxanne & Raquel to retain, but the star power and fan-pleasing title change has to be hard for WWE to pass up. That’s okay, The Judgment Day duo can regain the titles in a TV match that leads to the inevitable split for Flair and Bliss.
PC Tunney’s pick: Charlotte & Alexa – I want to see this happen, I really want to lol
I have no clue why!
Sami Zayn vs. Karrion Kross – Singles Match
Odds: Sami Zayn (–250), Karrion Kross (+180)
Zayn is favored with a 71% win percentage.
Zayn’s momentum has been on a roller coaster ride for, well basically his entire WWE career. Fueled by emotional storytelling and that Helluva Kick finishing move he’s perfected over years. Kross is the physical menace—the kind of throwback monster heel who wants to bury Zayn’s momentum once and for all.
- Who Should Win: Sami Zayn
- Who Will Win: Sami Zayn
Based on everything I say, you’d think I wasn’t a Karrion Kross fan…when in actuality I’m a huge fan of the performer. But the character stinks, in my opinion, anyway. He’s a legitimate bad ass, and should be featured as one. Sami Zayn, on the other hand, is beloved by many, and should be headed to a mega push on The Road To WrestleMania 42. And a win here only makes sense.
PC Tunney’s pick: Karrion Kross – “Kross was right.”
WWE SummerSlam 2025 – Night 2 – Sunday, August 3
Street Fight for the Undisputed WWE Championship – John Cena (c) vs. Cody Rhodes
Odds: Cody Rhodes (−300), John Cena (+200)
Cody expected to regain the WWE’s top title at a win probability of 75%
This is the culmination of years: WrestleMania rematch, street fight rules, and Cena’s impending WWE retirement looming. Cody is favored to reclaim the title, but Cena’s legacy and weaponized veteran instincts make this a volatile rematch. But it IS A rematch. Does Cody’s movie role have any impact on the booking? Recent WWE direction tells me no.
- Who Should Win: John Cena
- Who Will Win: Cody Rhodes
Seth Rollins cashing in on John Cena (after he wins) here would be golden, but I’m not betting on it. Instead, go with what we know: LOLCODYWINS.
PC Tunney’s pick: Seth Rollins – Another heist of epic proportions!!!
Hell yeah, Tunney. Hell yeah.
Intercontinental Championship – AJ Styles vs. Dominik Mysterio (c)
Odds: Dominik (−200), Styles (+150)
Mysterio expected to retain at 67%
Styles brings experience, speed and flash, but Dominik has equally mastered psychological warfare and home‑field advantage. Expect a tactical back‑and‑forth, with Dominik banking on interference and lineage to stay gold.
- Who Should Win: AJ Styles
- Who Will Win: Dominik Mysterio
I love the idea of Dominik Mysterio winning the AAA Mega Championship at TripleMania, and carrying that belt both in Mexico and on WWE Monday Night Raw. And I think that does happen. So why does he need the Intercontinental Championship if that’s the direction?
He doesn’t. But WWE likely wants to see him draped in gold, and having him hold both accomplishes just that.
PC Tunney’s pick: Dominik Mysterio – Looking forward to this match most. These two should steal night two.
Triple Threat Match for the Women’s World Championship – Naomi (c) vs. Rhea Ripley vs. Iyo Sky
Odds: Naomi (−1500), Rhea Ripley (+400), Iyo Sky (+750)
Naomi is a ….94% favorite to win? Seems crazy!
Naomi’s cash‑in and reign have been meteoric, but Sky and Ripley are hungry competitors who revitalized the division. This triple threat has finishers flying every which way—can Naomi dodge chaos and retain against the charging challengers? Or Ripley simply too popular to keep the title off of?
- Who Should Win: Naomi
- Who Will Win: Rhea Ripley
In an ideal world, this match closes Night 1. Of course, that ain’t happening, as it sits on the card for Night 2. It makes ZERO sense to take the belt off of Naomi so fast, but I think we are going to start seeing LOLRHEAWINS become a thing very soon.
PC Tunney’s pick: Naomi – Why cash in just to lose so soon?
Steel Cage Match for the United States Championship – Solo Sikoa (c) vs. Jacob Fatu
Odds: Solo Sikoa (−140), Jacob Fatu (+100)
Solo Sikoa sits as a 58.3% favorite to retain, the closest match odds of the weekend.
This grudge match in a cage is about revenge, incarceration-style brutality, and salvaging legacy. Fatu’s unpredictability (and recent arrest angle) ups the danger—so does Solo’s Bloodline backing and cunning brutality. The steel cage isn’t only meant to keep people out, it’s meant to be a weapon.
Which is good, because you know it ain’t keeping people out.
- Who Should Win: Soli Sikoa
- Who Will Win: Solo Sikoa
Jakob Fatu is meant for more than this program, and as we march into 2026, he will likely be headed down that road. But first, we need to see Solo and his MFTs victorious in a steel cage? Why? So they can ready San Diego, and the world, for the next chapter if Bloodline War Games!
PC Tunney’s pick: Solo Sikoa – Jacob should be moving on to bigger title scenes sooner than later.
Women’s Intercontinental Championship – Becky Lynch (c) vs. Lyra Valkyria
Odds: Lyra Valkyria (−200), Becky Lynch (+150)
Valkyria favored to regain the title with a 66.7% edge
Becky is the veteran queen, Valkyria is the rising star hungry to dethrone her. Their recent matches have been technical showcases—this time divisional prestige, animosity and payback are dialing things even higher.
- Who Should Win: Becky Lynch
- Who Will Win: Lyra Valkyria
I am really torn on this one–at least on the “Who Will Win?” side. Personally, I don’t see the star power in Lyra that others do. Her promos still aren’t there, and let’s be honest. Is she all that much better than released stars like Dakota Kai and Shayna Baszler?
PC Tunney’s pick: Lyra Valkyria – Because Bayley.
TLC (Tables, Ladders, & Chairs) for the WWE Tag Team Championships – Wyatt Sicks (c) vs. Andrade & Rey Fenix vs. Fraxiom vs. DIY vs. Street Profits vs. Motor City Machine Guns
Odds: Andrade & Rey Fenix (+130 favorite, ~43.5%), Wyatt Sicks (+150), Fraxiom (+250), DIY (+500), Street Profits (+700), MCMG (+1000)
Andrade & Fenix are (surprisingly) at 43% favorite to win here.
This six‑team TLC match is WWE admitting a mistake by spotlighting its tag division now. Expect insanity—and the champions have to survive a flurry of stunts if they want to protect the belts at the elite level.
- Who Should Win: The Wyatt Sicks
- Who Will Win: The Wyatt Sicks
There really is no reason to move the tag titles here… instead this is all about spectacle. This match likely opens up Night 2, and it will deliver. But I see no reason why Joe Gacy & Dexter Lumis won’t retain.
PC Tunney’s pick: Street Profits – This match should be a highlight of the weekend.
Final Thoughts for WWE SummerSlam 2025
SummerSlam 2025 is shaping up as a historic two-night WWE spectacle where legacy meets fresh blood, celebrity meets spectacle, and titles are on the line in every direction. The odds give us a blueprint of what the bookies believe—but wrestling is scripted to take us on a roller coaster ride of surprises. Let’s sit back and enjoy the ride!
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