11. Damien Sandow - 13 Years
Damien Sandow has been with WWE since 2002, with the exception of a year out he took in 2009. That's a remarkable amount of time to be under a WWE contract, and it makes him one of the most experienced wrestlers in the company. He was signed in 2002, with a run in OVW following, before some main roster matches on Heat in 2003. It wasn't until 2006 that he got a consistent main roster spot, debuting on Smackdown as Idol Stevens and being managed by Michelle McCool. However, it wasn't long until WWE relegated him back to developmental. He then left for a year in 2009, before returning to developmental in 2010. In 2012, he came back to the main roster as Damien Sandow. Although skilled in the ring and on the mic, he has fallen into irrelevancy and is a rarely used jobber nowadays. That tends to be a theme with these surprising veterans... they are kept around to either do jobs or do nothing.