WrestleMania XXXII The Undertaker v Shane McMahon

The Undertaker has WWE in his veins. He’s been a fixture in the company through thick and thin, destroying opponents and earning respect from the locker room for 25 years and counting. At WrestleMania, though, he’ll stand inside Hell in a Cell across the ring from someone born into WWE royalty and eyeing control over its flagship program Raw: Shane McMahon, the grandson of WWE’s founding father and son of WWE’s current Chairman.

Shane-O-Mac started his career in the WWE warehouse at age 15, fulfilling merchandise orders. In the 25 years that followed, Shane led several departments behind the scenes and rose to the position of Executive Vice President of Global Media, while also becoming a major player on WWE TV. But in 2010, he decided to leave WWE and create his own path, pursuing other business ventures in China, far from the shadow his father Mr. McMahon cast.

On the Feb. 22 Raw, though, Shane unexpectedly returned to WWE to interrupt his sister Stephanie McMahon from becoming the first recipient of the Vincent J. McMahon Legacy of Excellence Award. After Mr. McMahon lauded Stephanie for having a “good-hearted soul,” Shane cut off her acceptance speech, irreverently dancing to the ring in a suit and a pair of Air Jordan 1s — a testament to his laid-back, yet corporate, demeanor.