Jeff was on WWE television as a jobber at the age of 16 and he had his first televised match against Razor Ramon. Before this, him and his brother Matt had their own local federations called the TWF (Trampoline Wrestling Federation) and OMEGA (Organization Of Modern Extreme Grappling Arts). OMEGA was shut down when the brothers signed with WWE in 1998.
- "The Charismatic Enigma"
- "The Rainbow-Haired Warrior"
- "The Legend Thriller"
- Extreme Twist of Fate
- Swanton Bomb
- Twist of Fate
- Whisper in the Wind
- Diving Clothesline
- Driving Leg Drop
- Double Knee Facebreaker
- Sitout Jawbreaker
- Horizontal Baseball Slide
- WCW Tag Team (1 time)
- WWF Light Heavyweight (1 time)
- WWF Hardcore (3 times)
- WWF/WWE Intercontinental (4 times)
- WWF/WWE World Tag Team (6 times)
- WWE European (1 time)
- WWE Champion (1 time)
- World Heavyweight Champion (2 time)
- Ninth WWE Grand Slam Champion
- Eighth WWE Triple Crown Champion
- TNA World Heavyweight Champion (2 time)
Jeff finally captured the WWE title at Armageddon 2008 defeating the defending champion Edge & Triple H in a triple threat match. After 10 straight years of climbing to the top of the mountain, the charismatic enigma finally captures the most prized entity in the industry, becoming the top dog, headlining the WWE.
At WWE Extreme Rules, Jeff also captured the World Heavyweight title by defeating Edge in a Ladder Match. His title reign would be short lived by CM Punk who would cash in the money in the bank briefcase after the match, making Jeff having the shortest World Heavyweight title reign in the history of the WWE. At Night of Champions Jeff become a 2-time world champion by defeating CM Punk. At WWE Summerslam Jeff competed in a TLC (Tables, Ladders and Chairs) match with CM Punk and lost. Later that week at Smackdown Jeff would face Punk in a cage match for the World Heavyweight Championship but the loser of the match would be forced to leave the WWE. Jeff lost the match so Jeff then left and announced his retirement. In reality Jeff was retiring to rest many injuries he had such as a neck injury, two herniated disc and suffering from restless leg syndrome.
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