5 times WWE superstars had to be convinced to extend their contract

#4. Randy Orton - How The Viper teased a move to get a better offer from WWE

Randy Orton at TLC

Randy Orton's WWE contract was originally set to expire in the summer of 2020, and while he knew he was going to get a renewal, he decided to have a little fun to his benefit.

In late 2019, Randy Orton posted a picture on Instagram teasing interest in a move to AEW:

Speaking on Wrestling Observer Radio, Dave Meltzer stated that Randy Orton was deservedly playing both sides in hope of getting one last major contract:

"Maybe his contract’s up and he’s playing the game. And he should. I mean, he’s fixing to able to get a lot and lot of money if his contract’s up. And what is he, 38 years old? 39? So this is the time. This is the time to get that last big contract. He’s probably one of those guys who will want to work a minimal schedule and WWE is giving him a minimal schedule, he’s not out there killing himself."

Randy Orton eventually re-signed with WWE for five years after officials were quick to convince him when he teased interest in AEW. In November 2019, Randy Orton revealed that he signed a 5-year contract with WWE:

The 3 most dangerous letters in sports entertainment- #RKOjust re-signed with the 3 most dominant letters in sports entertainment- #WWE Looking forward to pi$$ing off the #WWEUNIVERSE for at least 5 more years #WWEBACKSTAGE @FS1 @WWE

— Randy Orton (@RandyOrton) November 6, 2019

Triple H commented on it as well, stating that he was glad to put the rumors to rest:

"I'm glad to put the rumors to rest. For almost two decades, Randy Orton has been a cornerstone of WWE...and Randy Orton will remain a cornerstone of WWE for a long time!"

Randy Orton never had any intention of leaving. He knew that at the time, WWE was offering big contracts to those who were thinking about making the jump to AEW. He simply played his cards right, but he knew that WWE would have to "convince" him to re-sign.