Tony Romo had himself quite the offseason, netting a 10-year, $180 million contract to remain with CBS as an analyst. Even though he doesn't like talking about the specifics of his new contract, he recalled a shocking conversation he had with Jerry Jones and Bill Parcells when he was with the Dallas Cowboys. Romo was interviewed on In Depth with Grant Bensinger and Pro Football Talk provided the transcription:

“Jerry Jones and Bill Parcells sit me down right before a preseason game … They’re like, ‘We need you to sign this deal for $500,000.’ I’m making the league minimum, $250,000 or so. I told them, ‘The only way you’ll play me is if you have something invested in me that makes you want to see if I’m worth it.’ I told them $2 million. ‘For that, I feel like you’ll want to put me in a game to see.’ Believe me, I didn’t want to do it. It was as nerve-wracking a situation as I’ve ever been in.”

Back in 2006, Romo was entering his fourth season with the Cowboys. The no-name quarterback began his career with Dallas as an undrafted free agent in 2003. Despite not throwing a pass in his first three seasons, Romo was able to successfully negotiate a $2 million signing bonus in 2006.

The Eastern Illinois product would proceed to start in 10 games in 2006. Over those 10 starts, he threw for 2,903 yards, 19 touchdowns and 13 interceptions. Now, after a successful 14-year career with the Cowboys, Romo is considered as one of the best commentators in football.

After his contract expired at CBS following the 2019 season, Romo was expected to be pursued by multiple networks. But before any networks could offer him a contract, CBS enticed him with the largest contract in sports analyst history. It's safe to say that Romo's negotiating tactics in 2006 helped him complete his latest deal with CBS.