At Wrestlemania 32 this weekend, Shane McMahon will return to the ring for a match against the event's most iconic figure—the Undertaker. It won't just be any match, but a one-on-one encounter inside Hell in a Cell, a 20-foot high steel structure the Undertaker made famous when he hurled Mick Foley from the top of it in 1998. At stake for McMahon in this bout? An opportunity to control the WWE's flagship program, Monday Night Raw. For the Undertaker, a loss means that his storied career will finally come to an end.
When Shane walks the aisle on Sunday, we'll have the answer to the most important question in all of this—which sneakers will he wrestle in? Since making his in-ring debut in 1999, Shane-O-Mac has been a surprisingly dedicated sneakerhead, competing in some of the greatest pairs Nike and Jordan Brand have to offer. He didn't miss a beat when he recently returned to Raw after a six-year absence, doing so in the always-appropriate Air Jordan 1. That move, presumably, landed him a spot on Jordan Brand's seeding list.
Before we find out what Shane has lined up for 'Mania, here's a look at his greatest sneaker moments inside the squared circle.
31. Nike SB Dunk High "Papa Bear"
Event: Monday Night Raw
Date: 05/14/07
Before Jonathan Coachman became an ESPN anchor, he was the interviewer fans loved to hate in the WWE. On this episode of Raw, he was sacrificed by the McMahons and thrown into a match with the physically imposing Bobby Lashley. He lost, and he lost badly. Shane accompanied "Coach" to the ring in "Papa Bear" Dunks, perhaps his most surprising wear to date.
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28. Air Jordan 1 Retro High "Bulls"
Event: Monday Night Raw
Date: 02/22/16
After a six-year hiatus from the company, Shane returned to Raw to address his father and sister's business practices as the "authority" of the show. The CEO's son said that he was promised a position of power prior to his absence and was back to claim what he believes is his in an effort to "save" the WWE. After some back-and-forth, Vince agreed to give Shane control of Monday Night Raw, but under one condition—that he defeats the Undertaker in Hell in a Cell at Wrestlemania 32.
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25. Air Jordan 3 Retro "Cement"
Event: Backlash
Date: 04/24/09
Opponent: Legacy (with Triple H & Batista)
In an unusual match, WWE Champion Triple H defended his title against Randy Orton as part of a six-man tag match. Shane sided with his brother-in-law, but wasn't successful in helping him retain the belt.
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22. Air Jordan 2 Retro "Wing It"
Event: Monday Night Raw
Date: 03/07/16
Now aware of his Wrestlemania fate, Shane returned to Raw for a microphone showdown with his father. The segment ended with Vince sending security to the ring to escort Shane out of the building, but as always, they didn't quite do their job.
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19. Air Jordan 1 Retro High "Shattered Backboard"
Event: Monday Night Raw
Date: 03/14/16
As one would expect, the first face-to-face confrontation between Shane and the Undertaker as Wrestlemania opponents didn't end so well for the Boy Wonder. The lasting image from this show will be his "Shattered Backboard" Air Jordan 1s taking flight as he was on the receiving end of a chokeslam.
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16. Air Jordan 3 Retro "Fire Red"
Event: Backlash
Date: 04/28/07
Opponent: Bobby Lashley (with Vince McMahon & Umaga)
The McMahons have never been interested in fairness, so to get the ECW World Championship away from Bobby Lashley on this pay-per-view event, they stacked the odds against him with a team of Vince McMahon, Shane McMahon and "The Samoan Bulldozer" Umaga. Fresh off a head shaving at Wrestlemania 23, a durag-clad Vince pinned Lashley for the title.
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13. Air Jordan 3 Retro "True Blue"
Event: Monday Night Raw
Date: 04/24/06
Opponent: Shawn Michaels
When Degeneration-X reunited in 2006, they were natural adversaries of the authority. On his night, Shane went one-on-one with arguably the WWE's greatest in-ring competitor, Shawn "HBK" Michaels. The image of him delivering his signature elbow to Michaels in "True Blue" Air Jordan 3s has been passed around sneakerhead circles for years.
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10. fragment design x Air Jordan 1 Retro
Event: Monday Night Raw
Date: 03/29/16
Looking to send a message before Wrestlemania 32, Shane woke up Brooklyn's Barclays Center when he viciously attacked the Deadman to open Raw. In vintage Shane style, he put the Undertaker through the announce table with an elbow off of the top turnbuckle.
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7. Air Jordan 3 Retro "Black Cement"
Event: Monday Night Raw
Date: 10/29/01
Opponent: Vince McMahon
Vince and Shane McMahon have squared off against each other in many matches over the years, none more violent than their famous streetfight on Raw. Shane, representing the newly acquired WCW, was on the verge of losing this match before an all-out brawl ensued.
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4. Nike Air Trainer SC High
Events: SummerSlam / King of the Ring
Date: 08/26/00 / 06/23/01
Opponent: Steve Blackman / Kurt Angle
Shane McMahon isn't and has never been a novelty act. The guy puts on actual great matches, none better than his King of the Ring bout against Olympic gold medalist Kurt Angle in 2001. Earning the respect of fans worldwide, Shane was dropped head-first on concrete, suplexed through a glass panel and Angle Slammed from a wooden plank on the top turnbuckle in a losing effort.
A year earlier, the defining moment of Shane's career took place in a match against "The Lethal Weapon" Steve Blackman at SummerSlam. Shane, the defending Hardcore Champion, took on the martial arts expert in a brawl that predictably spilled outside the ring. Attempting to put some distance between himself and Blackman, Shane climbed a 50-foot steel structure that was part of the stage. However, Blackman met him at the top and repeatedly struck him with a kendo stick until he fell to the ground. Blackman climbed about halfway down, jumped off the structure and hit Shane with an elbow to become the new Hardcore Champion.
Both of these moments took place while Shane was wearing a simple black and white Nike Air Trainer SC High. Bo knew a lot of things, but he didn't know hardcore wrestling.