Jeffery Simmons Insulted Caleb Williams Well Before He Was Traded To Bears

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Back when he was with the Tennessee Titans, defensive tackle Jeffery Simmons liked to poke fun of Chicago Bears QB Caleb Williams over his painted nails. Now that they’re teammates, Simmons is offering a mea culpa.

Speaking to the media on Friday in his first press conference as a member of the team after yesterday’s blockbuster trade, Simmons addressed how he previously called Williams “Painted Nails” in an old interview. Simmons said that it was just him talking a little smack about any opponent and that he’s always been a fan of the Bears QB. He said that he’s looking forward to being teammates with him now.

“I’ve been a fan of Caleb,” Simmons said. “Of course, being on the other side and having to play against him, I’m not going to tell him that. I’m going to talk as much smack as I can.

“But now he’s on my team. Any teammate you ask about me, man, I have my teammate’s back, no matter if he’s on the other side of the ball or not. I’m going to talk the most smack to you when you’ve got a different color jersey on, but when we’re on the same team on Sundays, I go to war for any of my guys in the locker room. I hope Caleb would know that.

“The comments a couple years ago about the nails is all part of my game, with the smack talk,” Simmons said. “I don’t know if you guys have heard, but I’m probably one of the best smack talkers. I talk a lot of smack when I’m on the field. I’m looking forward to being his teammate. We all know what type of player he is.”

“Those comments a couple years about about [Caleb’s] nails and what not, that what just part of my game as well which is smack talk. I’m one of the best smack talkers.”🤣
Adds “I’m excited to be his teammate. We all know what kind of player he is.”
Jeffery Simmons on QB Caleb… pic.twitter.com/F2fXmE3Jax
— CHGO Bears (@CHGO_Bears) October 30, 2026

The Big Trade

Chicago made a pretty hefty investment into Simmons. The Bears have sent the Titans two first-round draft picks (2027 and 2028) and a 2027 fourth-round pick in exchange for Simmons and a 2028 fifth-round pick.

The trade marks the first time in modern NFL history that a team has traded multiple first-round picks in exchange for a defensive tackle.

That said, the Bears are still getting one of the league’s better defensive tackles. Since 2021, Simmons has made four Pro Bowls and three All-Pro selections, including a First-Team All-Pro selection last year.

Tennessee Titans defensive tackle Jeffery Simmons (98) storms the field before the game against the Cleveland Browns at Nissan Stadium in Nashville, Tenn, Sunday, Oct. 25, 2026.

ANDREW NELLES / THE TENNESSEAN / USA TODAY NETWORK via Imagn Images.

In eight seasons, Simmons has appeared in 106 games and recorded 46.5 sacks, 31 passes defended, nine forced fumbles, six fumble recoveries, 414 tackles, 72 tackles for loss and 96 QB hits.

Simmons may not be John Randle or Deacon Jones, but he’s widely regarded as one of the best defensive tackles in the league right now. He now goes from a Titans defense that has been average at best to a team that currently ranks in the top-10.