- Jeff Jarrett
We’ll start things off with an individual that has been on the bad side of WWE management for a long time: Jeff Jarrett.
A member of the famous “Jarrett” wrestling family, which includes father Jerry Jarrett, Jeff has found himself in the dog house many times. This has come as a result of Jarrett’s frequent changing of sides during the “Monday Night War”, with Jarrett going over to work for WWE’s rival World Championship Wrestling on more than one occasion.
The straw that broke the camel’s back, however, was when Jarrett held up the WWE for $300,000 dollars to work without a contract and to drop the Intercontinental Championship (which he held at the time) to rival Chyna at No Mercy ’99. As anyone in the business could tell you, no one holds up Vince McMahon, and Jarrett’s extortion saw him walking out the doors of the WWE after his match and never returning.