• JOSH PAIN: 6 REIGNS (2x Heavyweight, 3x Extreme, 1x North American)

Being the only man to have held three different singles titles in the DWO, Josh Pain has also had a longer career here than most men on this list but with quantity comes quality as "the Anti-Hero" has been sure to make each of his reigns as champion memorable. BIGGEST VICTORY: After seemingly falling out of the title picture, Pain (then known as The Prophet Joshua) competed twice in one night at Crossroads 2009 to capture his first Heavyweight Championship in a match against Chad Thomas and champion Joe Quesada, who had just won the belt the month before.

  • HOBO HANK: 3 REIGNS (1x Heavyweight, 1x Extreme, 1x Tag Team)

Another seasoned veteran long before making an impact in Destiny Wrestling, it only took Hobo Hank just over a year before his first championship victory and he has been nearly impossible to stop since, having been only one of two men to simultaneously hold two belts back in 2010. BIGGEST VICTORY: Being Extreme and Tag Team Champion at the same time is a huge feat but nothing can even compete with Hobo's victory against Joe Quesada at Day of Destiny VI that took place inside the confines of a cage, securing the veteran's very-first Heavyweight Championship anywhere.

  • THUNDER: 2 REIGNS (2x Tag Team Champion)

For Thunder, it only took him two runs as a champion for him to break the 365 day mark, and he owes a little bit of his success to his longtime buddy Mosh Pit Mike who, when teamed together, dominated the tag team division in Destiny Wrestling for nearly two years strong. BIGGEST VICTORY: After Hobo Hank single-handedly won the Tag Team Titles in April, everybody was curious as to who he'd name as his partner and at Kayfabeulous 2010, Thunder was revealed as his pick...but it didn't last long as he turned on his longtime friend and became a co-champion with Pain Inc.

  • MOSH PIT MIKE: 3 REIGNS (1x Extreme, 2x Tag Team)

Mosh Pit Mike has held numerous championships all over the southwest but his expertise in the tag team scene is what really cemented his spot right behind Josh Pain as his last Tag Team Championship run holds the record for the longest single title reign in DWO History with 539 days. BIGGEST VICTORY: As part of Pain Inc. with Thee WidowMaker, Mosh had already won tag team gold in every promotion he ever competed for but at Day of Destiny IV, him and his partner in crime further cemented their tag team legacy by becoming the first DWO Tag Team Champions.

  • JOE QUESADA: 3 REIGNS (2x Heavyweight, 1x North American)

Being the man with the least amount of experience on this list doesn't mean anything to Joe Quesada as he has been turning heads left and right since debuting in 2008...and it's come with some title victories as well as he is one of only two men that have been able to win the Heavyweight Title twice. BIGGEST VICTORY: 2010 was the year that Quesada stopped the nice guy routine and at Day of Destiny V, his master plan finally came to fruition as he was shockingly given an immediate title match for Josh Pain's newly-won Heavyweight Title after just winning it from Chad Thomas.

  • JOHNNY K: 3 REIGNS (3x Extreme Champion)

Johnny K is the one guy here who has gone the longest amount of time since his last championship win but lucky for him, his dominance of the Extreme Division back in the early years of the DWO was enough to make him the final member (for now) of this illustrious club. BIGGEST VICTORY: During the first few years of Destiny Wrestling, Johnny was always trading the Extreme Title back-and-forth with Josh Pain but he finally got the upper-hand of his longtime rival at SuperKlash '08 when he won the war and captured the strap for a then-record of three-times.