#2 Triple H - 14 Reigns

The only reason why Triple H is not the most coveted World Champion in WWE history is that Vince McMahon found John Cena, who emerged as the biggest superstar in the history of the company during the second half of the 2000s. Otherwise, Triple H would have definitely eclipsed even Ric Flair's record of 16 World Titles long, long ago.
However, it would be unfair to say that Triple H didn't deserve or earn any of his 14 World Titles. His run as the WWE's top heel against The Rock in the early 2000s was easily the best work of his career, and it did earn him a total of five WWE title reigns. However, after the summer of 2002, he became more synonymous with the World Heavyweight Title.
Cody Rhodes' uncle is a WWE Hall of Famer. More details HERE.
In fact, HHH, who had five reigns with the belt, held the title for such a long time between 2002 and 2005 that people started getting irritated with his constant presence. While his ninth and final reign with the WWE Title in 2016 was not very well received, his 210 day run in 2008 on Smackdown was easily the best thing on WWE television and produced some of the best matches he has ever wrestled in his career.