#1 Ted DiBiase - 26 Years and 1 Month

Amazingly, the Million Dollar Man Ted DiBiase never held the WWE Championship, despite having all the tools. While he had an unfortunate lack of singles Championships in his WWE career, he did manage to become a three-time WWE Tag Team Champion as apart of Money Inc., with IRS.
Money Inc. would trade WWE Tag Team Championship victores with Rick and Scott Steiner in 1993, where they won them for the final time on the 16 of June, and lost them for the final time to the Steiners just three days later at a live event. This would be the last time DiBiase would hold gold in WWE, that is at least for another 26 years.
With the longest gap in between WWE Championship reigns, after just over 26 years, DiBiasie would win the WWE 24/7 Championship in July, 2019. DiBiasie had appeared on the RAW Reunion special and purchased the Championship from fellow Hall of Famer and runner up of this list, Alundra Blayze. DiBiasie would lose the title to Drake Maverick later that night after being pinned in his limousine.
In between this historic title gap, Ted DiBiase did briefly hold the PWF Tag Team Championships with Stan Hansen in 1993.
Becky Lynch has been challenged HERE.