December 14 was the 14th anniversary of Jeff Hardy winning his first and only WWE Championship. In route to becoming champion, Hardy was rumored to win the Money in the Bank ladder match at WrestleMania 24.

On the latest episode of The Extreme Life of Matt Hardy, it focuses on the road to the WWE Championship for Jeff. On the March 3 episode of RAW, Jeff is a guest on Chris Jericho‘s “Highlight Reel” when Jericho attacked him from behind. Shortly thereafter, Jeff dropped the Intercontinental Championship to Jericho. This was due to a failed drug test and 60-day suspension as it was his second violation.

Matt confirmed the rumor that his brother was scheduled to win the ladder match and they had decided to make him champion. Freddie Prinze, Jr. was part of creative at this time and had been tasked with making Jeff the WWE Champion.

“I know Freddie Prinze had been given this edict to get Jeff ready for the championship. This was around the time too that he had started to paint his face again. I think they started to lean into some stuff that was very Jeff Hardy-ish.”

“Jeff was in Mexico on an international tour and its at some point there he ended up taking something, some sort of pill or substance — I don’t know if it was for his back or whatever it was — but he ended up getting popped in a drug test. One of the things I remember from the story is that Michael Hayes called him at home and was like, ‘what is going on here? I can’t believe you did all this. Vince is going to call you in a few minutes, so be ready to answer the phone.’ Vince called and was like, ‘what the fuck have you done?’ I guess they taiked it through and Jeff said they spoke for a while and they seemed to be kosher. Jeff just apologized and regretted taking it.”

Matt also discussed the “Nashville incident” where Jeff was removed from a plane by police. The brothers and Shane Helms had been celebrating someone’s birthday the night before and stayed up too late. The next day, Jeff managed to get either liquor or beer and was “buzzed.”

Matt tried to get his brother to eat and Jeff smashed the sausage biscuit into the ground while laughing. Matt & Helms told him to “be cool.” Jeff talked to everyone that was boarding and someone with the airline realized he might be drunk. They asked him to leave and he said no, he’d just sleep on the flight. He was the escorted off the plane by police. This incident upset some of the locker room and Jeff lost some support.

Jeff eventually beat Edge and the WWE Champion Triple H at Armageddon, even though Triple H didn’t think Jeff was reliable enough to be champion. Matt says seeing his brother become WWE Champion was one of the highlights of his career.