The Undertaker’s 10 Biggest Regrets In His WWE Career

1. Staying Around The Business Too Long

Ultimately, The Undertaker never envisioned wrestling into his late forties. By the year 2001, he was already a very rich man, and already in physical pain from over a decade on the road. He was certain that he’d be retired by the end of the 2000’s decade.

Regretfully, WWE business took a big nosedive in 2004, meaning that the WWE needed him more than ever as the years went on. He was a true star and unfortunately no new stars were coming through. The advancement of the streak had compounded the fact that WWE relied upon him, with the streak being one of the key selling points in WWE’s year.

Just like Shawn Michaels before him, The Undertaker ended up unable to say “no” to Vince McMahon. He felt compelled to the company and kept working beyond his envisioned retirement date.

Looking back, Calaway will acknowledge he stayed around the business too long. He should have ideally retired alongside Shawn Michaels in 2010 – everything after that was just WWE trying to milk the cash-cow.

On the other hand, the billed “end of an era” match with Triple H in 2012 was surely a fitting retirement. Instead, the WWE got Taker back for more, and he now has the dismay of possibly retiring with the Lesnar stinker as his last bow.

Most importantly, The Undertaker will regret not having had more of a family life. He retired from the full time road many years back, but the physical toil of his WWE career could be haunting him for years to come.