One of the first steps after Jeffery Simmons joined the Chicago Bears in a trade on Thursday was choosing a jersey number.

Simmons has since done that, taking No. 99, which is not the No. 98 he wore with the Tennessee Titans. We figured Simmons simply took 99 because Montez Sweat, his former college teammate, already had No. 98 and wasn't willing to give it up.

However, that turned out not to be the case. Sweat actually did offer up his No. 98 to Simmons, but the four-time Pro Bowler decided to decline.

Why Simmons chose 99 over 98

Why did he do that, you ask? Well, Simmons thought it would be good to get a new number amid his fresh start in Chicago.

"I was actually on the plane when I was headed out here yesterday, and I was just thinking, this is something new for me. This is a new beginning. I feel like this is just a new chapter in my life," he said.

"I knew Sweat didn't mind giving me 98, but I also said I didn't want to get the number from him, one," Simmons added. "But two, it was more I wanted something new. I wanted this to be a new chapter, a new reason behind everything I do. I just said it's only right to go with a new number and that was 99. And 98 +1 = 99."

It isn't clear if Sweat had any dollar amount attached to giving up his No. 98 to Simmons, but Simmons definitely could've afford it with his $105 million deal.

Fresh start and a chance to win

It makes total sense for Simmons to want a completely fresh start. Not only is he going to a new team, he is completely flipping the script by going from a rebuilding squad to one that looks like it could compete for a Super Bowl in 2026.

The closest Simmons has come to a Super Bowl was his rookie season, when the Titans made an improbable playoff run to the AFC Championship Game where they fell victim to the eventual Super Bowl champions, the Kansas City Chiefs.

Since then, the Titans put together two more winning seasons in 2020 and 2021, but they failed to win a playoff game in those campaigns.

Since 2022, the Titans have been a mess, with the team posting a 20-55 record in that span. Simmons also played under three head coaches, Mike Vrabel, Brian Callahan and Robert Saleh.

There was also significant turnover at the quarterback position, with the Titans going from Ryan Tannehill, to Will Levis, to Cam Ward, with Ward looking like he won't pan out.

Barring something unforeseen, the Bears should not see that kind of turnover at head coach or quarterback. Both Ben Johnson and Caleb Williams look well entrenched in their roles, and as long as they're doing their thing, the Bears should be in great shape.

Now, Simmons will look to be one of the pieces that puts the Bears over the top to a Super Bowl that has alluded Simmons since 2019, and Chicago since 1985.