The build for this match is so on point. Instead of taking his loss to Taker and moving on with his life like all the other victims, Shawn refuses to let it go. In his arrogance he claims that he "wrestled the perfect match, and made one mistake." He knows he can beat the Undertaker. This is so consistent with Shawn's character. Every big feud he had during his comeback - with Hunter, with Jericho, with Cena, with Angle, with Edge, etc. - was based around Shawn's belief of "I am the better man" or "I am better than you" or "You are no Shawn Michaels". Shawn always acts like the best, talks like the best, wrestles like the best. So in this case he believes he's better than someone - Taker - but the only way to prove it is to beat him, so that idea takes hold of him and he becomes obsessed with the rematch. You can see it in the way he's so sure he will win the Rumble, in the way he desperately clings to the ropes before he's eliminated and then throws a tantrum afterwards, in the way he lashes out at Hunter, at officials, until he finally hatches a plan to get Taker to notice him - screw him out of the title at Elimination Chamber.
The downside is that in doing so he's royally pissed off Taker, who asks for the ultimate price for granting his wish: his career. Shawn doesn't even hesitate to put his career on the line, not only because he's so sure he can beat him, but because "if I can't beat you, I have no career." And he truly means it. This is Shawn Hubris at its finest, he is so convinced that he's the greatest, better than anyone on earth, that he believes that if he can't accomplish the most difficult, impossible Everest climb in the history of wrestling - beating Undertaker at Wrestlemania - then he should just pack it in altogether. He's either the greatest of all time, or he's nothing. He's given himself one chance, but it's one that is virtually impossible to pull off.
But he sure as hell is going to try. He starts off by mocking Taker's throat slash. As established in the first match, Shawn is fighting an uphill battle against a guy this big and bad and NEEDS Taker to make mistakes if he's to have a fighting chance. So even moreso than the first match he's going full on antagonist, trying to goad Taker into sloppiness. Problem is, he's pissing Undertaker the fuck off. Taker goes postal and unleashes on him, raining down punches, tossing him around, sending him flying off the Big Boot, nailing Old School all in short ord-oh. Did you see that? He landed kind of funny there. I think it's his knee. He's...is he limping? Oh shit!
I love everything about this, from Taker's subtle selling and trying to cover it up, to Shawn spotting it and acting like he couldn't believe his luck, to King's sad lament for Taker that the last thing you want in a big match is to pick up an injury. Shawn had a plan to goad Taker into making mistakes, but what he got instead was even better - an injury! It's the happiest of accidents for Shawn, this is just what he needed. He goes after the leg, he uses his figure four, he even uses the ankle lock. Taker for his troubles still fights back, and still manages to get his shots in on Shawn in the meantime, but his leg bothers him the whole way, and suddenly this thing is looking like a fair fight. This is the great equalizer.
At one point Shawn knocks Taker off his feet again and Kips Up, and Taker is all "Fuck this shit!" and BAM Chokeslam! His leg must be bothering him because Taker has decided already that it's time to go home, he's had enough of this shit. Soon after they spill outside and Shawn goes for the moonsault, Taker catches him and BAM, Tombstone on the floor! Throwing that shit out already, plus the frantic way Taker throws him back inside to get the cover...I hate to use the word again but Taker is looking kind of...desperate again. He's trying to contend with Shawn wrestling for his life AND having a bad knee at the same time.
And it's not working. He goes for the Last Ride, but Shawn pulls his hair and his stupid fucking knee buckles and he collapses face first. Shawn goes for the elbow and Taker gets his knees up to counter but JESUS FUCK I just let him elbow my stupid fucking knee! He resorts to using Hell's Gate from his back but Shawn rolls him into a pin to counter it (once again, this had never been done before, and is another example of escalation that doesn't involve kicking out of finishers). Soon enough Shawn finds an opening to hit the superkick, but naturally it's not enough. As we've established, Shawn's response to a superkick kickout is MOAR SUPERKICKS, and as he tunes up the band this time Taker knows it's coming and counters with the Last Ride. Again, it's not enough.
Last year Taker reacted to the Last Ride kickout by going up top, taking a risk and making a mistake. This year he's determined to fix that mistake, so instead of doing something out of character he sticks to what he knows - badassery - and tosses Shawn outside and tries to kill him through the announce table. But once again Shawn finds a superkick at just the right moment, and with that opening he sticks to what he knows - high risk moves - and hits the moonsault off the top through the table and THROUGH TAKER'S STUPID FUCKING KNEE.
Whether it was the most pinpointed dive in wrestling history or the most serendipitous botch in wrestling history the result is the same - Shawn nailed that giant moonsault right on Taker's bad leg. King once again was super at this moment going all ashen-voiced and "I swear to God I think his leg's broken." Taker was selling like a demon and at one point was CRAWLING OVER THE BARRICADE TRYING TO GET AWAY. The Undertaker. Fleeing. Shawn is hopped up on the fumes and lurches Taker back into the ring, watching him take an eternity to drag himself up into one last, sad, final super-KICK OUT MOTHER FUCKER.
Oh damn that's right! I forgot again! Taker is a BADASS ZOMBIE COWBOY DEADMAN and won't go down even if you break all the legs in his God damn body. Fuck you! Taker is so fucked at this point though, you should see the struggle it takes him to get up from here. He's grabbing the ropes to pull himself but like he can't even put his feet on the floor so he's doing this weird horizontal pull that goes nowhere, it's so pathetic and brilliant. But he finally gets up and Shawn, in his infinitely creative wisdom, goes for another superkick (!) but Taker manages to counter with a Chokeslam.
Taker can still barely move but you get the feeling he's just blocked Shawn's last big punch. What else can Shawn really do? He certainly can't seem to think of anything other than more superkicks. Shawn is Shawn, he does things HIS way and it has always worked out for him. He's always been "the better man", always been the best. And now finally, after all of these years, all the opponents, all the matches, he has finally, surely, definitely come up against someone he just can't beat. Someone whom he's not better than. This is where he falls. And since he's either the best, or he's nothing, when he falls his career falls with him. This is it. This is the end. Taker picks him up and ends him with the Tombston-OH HE KICKED OUT.
Oh man, I am so forgetful today! This guy is Shawn Michaels motherfuckers! The Heartbreak Kid, the Showstoppa, the Main Event, the Icon. If he's going down, he's going down with the absolute fight of your fucking life. At WM25 Taker was shocked beyond belief that he kicked out of the Tombstone. Here he is just fucking MAD. He is angry that this fucker has the balls, has the fucking gumption to disrespect the Tombstone once again. If he has to kill him to put him down, then he's going to kill this asshole. He drops the straps once again and...looks down on this poor, pathetic, quivering mess of an...old man. And the anger leaves him. "Stay down!" Just stay down man, you don't have to kill yourself over this. You can be the second best ever, it's OK. Shawn sees the pity in Taker and takes SO MUCH fucking offense. He's Shawn Michaels damn it, he'll never lay down as long as he lives. He WANTS to be killed! So boom, throat slash, BITCHSLAP, and Taker's rage returns with a fucking vengeance and he KILLS HIM WITH THE JUMPING TOMBSTONE OF FUCKING DEATH.
I like the symmetry of starting with the throat slash and pissing off Taker, and then ending with it. That was Shawn's play, and by God he was going to see it through. The finish with Taker having to put Shawn down for good also hearkens back to WM24 when Shawn put Flair down. It's almost like a cycle now, and its importance becomes increasingly apparent as we get into the Hunter matches. Even though it's not a Streak match, Shawn vs Flair was kind of the precursor to these matches. And afterwards we get Taker showing another rare glimpse of humanity, holding his hand out for Shawn to shake as a show of mutual respect. The kind of respect Taker shows to someone who pushed him far beyond his limits, more than anyone else had ever before. Taker might not even realise it yet, but the lengths he had to go to to defeat Shawn would have a lasting effect on him. In some ways, this was the beginning of the end.
This match is as good an example as any of the kind of bone-headed hubris that Shawn wrestled with. I don't think he's ever been more obstinate than in this match. He had one way and only one way of doing things: Being Shawn Michaels. He didn't need to change his game after WM25 because he was CONVINCED that he'd wrestled it perfectly and it was only the moonsault counter that did him in. He was convinced, as he ever was, that he just needed to Be Shawn Michaels as well as he could and he'd win, because he's better than Taker, better than anybody. And he even lucked into the luckiest of fortunes - Taker injures his knee! So he goes to work on that as well as doing all of the Shawn things. He hits superkicks, and when they don't work he tries more superkicks. He goes for big moonsaults to the floor. It's all very...Shawn-y. The one new thing he tried - the Ankle Lock - was only due to Taker's leg injury and Shawn having to come up with ways to work it over. In a funny way it's like the only thing he could think of was that Mania a few years ago...he had to tap to the Ankle Lock, so it must be good! Offensively he was so very...unimaginitive. It's like the hubris had taken over and rendered him incapable of doing anything other than what he always does.
And ultimately it was his undoing. His offensive predictability at key moments allowed Taker to make his counters and recover from the injury that would otherwise have hampered him a lot worse. He saw the Kip Up coming and immediately hit a Chokeslam. He saw the moonsault coming and caught it. He saw the elbow coming and got his knees up. He saw the superkick coming and hit the Last Ride. Even at his most vulnerable, after he endured the table bump and a superkick and couldn't move, Shawn did the one thing he could have guessed was coming - tuned up the band AGAIN - and Taker was able to avoid it one more time, leading to the finish.
Honestly the worst thing about this match is Matt Striker shitting himself all over it. I am not even close to being able to decide which of the Streak matches I like the most or least, but I think this one is probably the least pleasant to sit through simply on account of rolling my eyes every five seconds at the shit coming out of Striker's mouth. It's a shame he had to taint Shawn Michaels' retirement match like that. But whatever. I just watched the greatest wrestler ever go out on top of the world. Fuck all y'all.