12. No Lengthy Title Reign In His First Six Years With WWF
The Undertaker was one of the biggest stars of WWF's Cartoon Era and subsequent New Generation push. Yet he only held the WWF Championship for six days in his first six and a half years with the company. He defeated Hulk Hogan for the title at Survivor Series 1991 and then jobbed it back the next week. He wasn't champion again for over half a decade. That was absolutely a missed opportunity on WWE and Vince McMahon's part. The title was wasted on guys like Diesel for a whole year in 1995, a big man act that had nowhere near the skill of Mark Calaway's big man style. There were also runs for Yokozuna and Sycho Sid with the belt, both big man workers who weren't as skilled in the ring as The Undertaker. Even Bret Hart's lengthy runs were lacking a certain spark. WWF business was tumbling in the 1992 to 1997 period, yet McMahon never thought to put the belt on The Undertaker for a second time until March 97 when Shawn Michaels couldn't compete at WrestleMania 13 due to injury.