WWE's The Last Ride paints a very detailed and intriguing picture of the Undertaker, aka Mark Calaway, in the twilight of his career. He's still searching for his swan song, "chasing that dragon," as his peers put it, which has led to many regrets such as the botch-filled brawl against Roman Reigns and the awful Crown Jewel fight with DX.
However, it has led to some epic redemption moments against the likes of John Cena, as the Dead Man tries to find the perfect high note to go out on -- a pursuit which has even made him jealous of the retired Shawn Michaels. In the fourth episode, "The Beast Within," we actually get more insight into why he's reluctant to retire -- and it's a secret not too many of his colleagues know about.
Initially, it does seem like he's motivated partly by an undying loyalty to Vince McMahon -- the big boss who admittedly can't let 'Taker rest in peace and wants to keep him in the WrestleMania showcase. However, when the Dead Man was omitted from the Show of Shows last year, we see him squirming as he watches others in the spotlight. As he sits in the control room, young guys greet him and the oldster even calls himself the "godfather," indicating his time is passing.
Edge speculates that his reluctance to retire may come from pride and ego, while Batista contends it's like that partner you can't let go of. But Triple H reveals that the real reason it's so hard for the Undertaker to retire is because he sees the business as his child. As someone who was there since the '80s, building up the industry and watching it evolve from wrestling into sports entertainment, he has just as much stake in the industry as McMahon. It's why he kept the sanctity of his character and didn't do marketing spots in the past -- to protect his baby.
He helped nurtured and raise WWE, which is why he always pays meticulous attention to detail backstage when he's not performing. It's also why he was angry he couldn't have a say in things like the Montreal Screwjob as he doesn't want anyone or anything messing with his kid. No wonder he beats himself up so much when he has a bad match or looks out of touch. He demands perfection, not just of himself, but of each and every event he's part of.
As good as 'Mania can get, it'll always be imperfect to the Dead Man without his participation in it. It's why Triple H believes he's addicted to it -- like any parent who always wants a say in their child's life, 'Taker needs wrestling to need him. That is why he's all too ready to answer McMahon's summons, because parents usually jump at the chance when their kids need them, even when they're in college or married. Simply put, Undertaker just isn't ready to see the business head off to university without him as he doesn't think he's imparted all the lessons he has to teach yet.
Triple H confesses that seeing Undertaker struggling to let go of his baby is hard, but they all go through it. Some, like him and Edge, are still going through it, while others like Batista have successfully transitioned into being part-timers who only get their fix every so often. But, they know they're not parents to the WWE in the same sense that 'Taker is, and it's why he's entitled to make the call to go out on his terms.
He thinks the business has a lot to accomplish, which is why he wants to groom the new generation like Reigns and leave it in good hands with epic matches against the likes of A.J. Styles. To Undertaker, class is still in session and he wants to pass on every ounce of knowledge to the kid that he and the McMahon family 'sired.' Before he'll be ready to leave, he'll need to know that his baby, the WWE, will be left in good hands with people he trusts.