Rich Weighs In on the Bears’ Blockbuster Trade for Titans All-Pro DT Jeffery Simmons

On Wednesday's show, Rich and the crew ran through who should sell at the deadline. Tennessee wasn't even on the list. Then the Titans sold Jeffery Simmons to the Chicago Bears, and Rich came in with one conclusion: in Chicago, now is now.

"Not in my wildest dreams did I think the Titans would sell Jeffery Simmons," Rich said, "until the Bears said, 'How about two ones and a four?'"

The Titans sent back a fifth-round pick in the deal, which Rich could not let go. He imagined Ryan Poles wondering where that fifth came from, then compared it to buying a house, when the deal is basically done and you start wondering whether to ask for the outdoor furniture. The crew had the answer: "100% need the washer and dryer."

What it says about Tennessee

Rich offered all due respect to Titans fans before delivering the verdict. "It means that we're done here," he said. Robert Saleh essentially made Simmons available for a certain price, and the fact that somebody hit it "just goes to show you that the Titans are retooling."

Why the Bears pushed in now

The bigger message is in Chicago. "What this means is Ryan Poles and the Chicago Bears feel like now is the moment," Rich said. "Now we go for it."

He sketched what Simmons does for a defense that is coalescing, especially once Sweat comes back: a force in the middle saying "not today" to Jahmyr Gibbs, Josh Jacobs, Christian McCaffrey, Kyren Williams, Blake Corum, Kenneth Walker or any back on the schedule. "And any quarterback that thinks that they're not going to get Jeffery Simmons stopping a run on the way to the quarterback, they're sadly mistaken," Rich said. "He's that good."

The timing matters too. Making the move now instead of next week means Simmons can clear his physical, send "a jolt through the building," and potentially play Monday night in Seattle. That puts him across from the Seahawks' own newest addition, Quenton Nelson, most of the time. "So the Bears are like, 'Okay, we see your Quenton Nelson and we'll raise your Jeffery Simmons,'" Rich said.

Rich walked through the rest of the road: Bucky Irving and a downhill run game the next week, a bye, two games against Detroit, a week 15 trip to Buffalo with James Cook and Josh Allen, and a closing game at Minnesota that could be for the division. He noted Minnesota handed Chicago its first loss of the season, the game where Caleb Williams hurt his hamstring.

Caleb Williams is ready

Part of why this is the moment, Rich argued, is that the quarterback is officially ready. "Our own two eyes see it," he said, so the head coach, the general manager and the locker room see it too.

He contrasted it with a year ago, when the Bears were digging out of an 0-2 start after Williams was fed Ben Johnson's entire system "through a fire hose." Then he played Johnson from Wednesday. "No one's more critical of him than himself at this point," Johnson said, crediting Williams for taking care of the football, a higher completion percentage and some of his more accurate run-after-catch throws. "He loves that criticism. He loves to take that and he chews on it," Johnson said. "He's just matured a lot in that regard, taking a game plan, downloading it, and being able to bring it to life on a fairly quick basis."

"We were all wondering when is now going to finally arrive," Rich said. Williams, for his part, hailed the trade on Instagram with a simple "Good morning world."

Painted Nails meets his new teammate

There's some history. Simmons has been on the show once, the day after Rich's birthday in the 2024 offseason, and Rich pointed out then that the Titans would be the first team to face Williams, the heralded first overall pick out of USC. The show replayed what Simmons said about facing "Painted Nails" in week one. "I can't wait to say that to him," Simmons said back then. "It's going to be one of them games."

"Now all the hype's around Jeffery Simmons joining Painted Nails," Rich said. "They're going to paint the town maybe together, right?"

For any Bears fan wincing at two first-rounders and a fourth, Rich had a simple answer. "If you are going down Michigan Avenue with a trophy, okay? If you're doing that, you will not think about that for one second," he said. "Now has arrived in Chicago."

A Monday night test in Seattle

Rich has said all offseason that Bears at Seahawks should have opened the regular season. He called it the would-be NFC Championship Game if the divisional round against the Rams had gone differently, and a better opener than the Super Bowl 60 reheat, which he said didn't light many fires. Now he's glad it waited.

Seattle is coming off a win over Kansas City where, Rich said, "the defending champs have re-entered the chat," and then added Nelson. Chicago is coming off its own win a week earlier, the defense has been balling out, Williams has looked the part since returning from injury, and now the Bears add Simmons. "Put it all to the test," Rich said. "Oh, baby. What a great way to start week eight."