Legendary Linebacker Mike Singletary Boldly Predicts Chicago Bears Will End Playoff Drought and Shock the NFL This Season

Chicago Bears legend Mike Singletary is never one to mince words. Known throughout his Hall of Fame career for a steely-eyed intensity, bone-rattling tackles, and a fierce devotion to discipline, Singletary has always been brutally honest—on the field and off. So when the former linebacker, who helped define the famed ’85 Bears defense, offers a bold prediction about the current team’s playoff future, it commands attention across the NFL.

In a recent appearance on The Herd with Colin Cowherd, Singletary delivered a passionate, unexpected, and optimistic forecast for the 2025 season: The Chicago Bears will make the playoffs. No hedging. No vague language. Just a firm belief that the team he once captained as a player is ready to break through.

“I see a team that’s hungry. I see talent, leadership, and a quarterback who’s about to turn the corner,” Singletary said. “If they stay healthy and play smart football, this is a playoff team. Period.”

For a franchise that has only made the postseason twice in the last 13 seasons, such words carry weight—especially from a voice like Singletary’s. The 11-time Pro Bowler and former NFL Coach of the Year finalist is still regarded as the heart and soul of one of the greatest defenses in league history. His read on Chicago’s roster, especially its defensive makeup, carries credibility that few analysts can match.

Singletary’s optimism centers on the evolution of quarterback Caleb Williams—the 2024 No. 1 overall pick—who is entering his rookie campaign with monumental expectations. For most observers, projecting playoff success for a rookie quarterback is a leap. But Singletary doesn’t see Williams as most rookies.

“Caleb Williams isn’t your average rookie,” Singletary said. “He’s a guy with ‘it.’ I’ve watched his tape from USC, and he plays like a veteran. He can extend plays, he can make all the throws, and most importantly—he believes. The kid’s got that leadership presence you can’t coach.”

Williams, who enters his first NFL season amid significant hype, has impressed early in training camp, earning praise for both his playmaking and his command of the huddle. After enduring a carousel of signal-callers in recent years—from Mitch Trubisky to Justin Fields—the Bears believe they finally have their franchise quarterback.

But as Singletary sees it, Williams doesn’t have to carry the team alone. Instead, it’s the overall roster upgrades and culture shift within Halas Hall that have him confident. Chicago was aggressive in the offseason, adding veteran pieces like wide receiver Keenan Allen, defensive end Montez Sweat (via trade and extension), and linebacker Tremaine Edmunds, while also drafting Rome Odunze—a physical wideout from Washington—to support Williams in the passing game.

“When I look at this Bears defense, I see speed. I see youth. I see potential becoming production,” Singletary noted. “It reminds me a little of when our defense started clicking. You need dogs on that side of the ball—and I see a few dawgs in this group.”

He singled out second-year cornerback Tyrique Stevenson and linebacker T.J. Edwards as “tone-setters” on defense and praised head coach Matt Eberflus for bringing a renewed focus to discipline and fundamentals. “I like what Eberflus is doing. He’s old-school in the right ways,” Singletary said. “That defense is going to be top-10 by the end of the season.”

The Bears’ defensive unit showed flashes of excellence late last season, especially after the arrival of Montez Sweat, whose presence transformed the pass rush and created opportunities for the secondary. In the final eight games of the 2024 season, Chicago posted one of the league’s best scoring defenses—an overlooked stat considering their 7-10 finish.

Singletary believes that improvement was no fluke.

“When you see a defense gel late in the year, that’s what you build on,” he explained. “They’ve got a foundation now. The difference this season is they’ve got a quarterback who can make teams pay when they try to stack the box or blitz.”

Still, making the playoffs in the NFC won’t be easy. The division is loaded. The Detroit Lions are coming off back-to-back playoff runs and have one of the league’s most complete rosters. The Green Bay Packers, now with Jordan Love emerging as a true franchise quarterback, are surging again. The Minnesota Vikings are retooling but remain competitive.

But Singletary doesn’t flinch when asked whether the Bears can hold their own.

“I know what good football looks like, and I know when a team is about to surprise some people,” he said. “The Bears will be in that wildcard mix, and don’t be shocked if they push for the division.”

Singletary’s comments echo a growing sentiment among NFL insiders that the Bears are one of the league’s most intriguing “sleeper” teams in 2025. NFL Network’s Peter Schrager listed them as a “team to watch,” and ESPN’s Dan Orlovsky said in a recent segment that “if Caleb Williams plays even average, the Bears win nine games.”

Singletary believes nine wins may not be the ceiling.

“You win the games you’re supposed to win, then steal two or three more with turnovers and smart football,” he said. “That gets you to 10 or 11. That gets you in the dance.”

It’s a sentiment that has fired up Bears fans—long-starved for postseason success since their last playoff win back in January 2011. Soldier Field has seen plenty of heartbreak in recent years, from heartbreaking collapses to questionable coaching decisions, and a conveyor belt of quarterbacks who failed to meet expectations.

Now, with Williams, Allen, D.J. Moore, Cole Kmet, and a young offensive line anchored by Darnell Wright, the Bears finally have what appears to be a sustainable offensive nucleus.

Defensively, the identity is starting to resemble the hard-hitting, opportunistic style that defined Chicago during its glory days. Jaquan Brisker brings physicality in the secondary, while Andrew Billings anchors the line in the trenches.

“I used to talk about playing with pride—every down, every quarter,” Singletary recalled. “This team is starting to look like they understand that mindset. That’s how you change a franchise.”

As the preseason nears, the Bears remain one of the league’s biggest question marks—but also one of its most intriguing stories. Their schedule offers both challenges and opportunities. Opening the season with a marquee matchup against the Packers in Week 1, Chicago will have a chance to immediately assert its presence in the NFC North.

“It’s about making a statement,” Singletary said. “You beat Green Bay in Week 1? That’s a mental shift. It’s a shot across the bow.”

Beyond the wins and losses, Singletary’s passion for the franchise still burns bright. While he’s been away from coaching since a stint in the Alliance of American Football, he continues to serve as a mentor and speaker, often discussing leadership, accountability, and faith.

And in his heart, Chicago remains home.

“I’ll always bleed navy and orange,” he said. “I want to see this team rise again. I believe this is the year they take that step. It’s time.”

As the NFL prepares for another rollercoaster season, few predictions will resonate more than this one from Mike Singletary. With a career forged in toughness and truth, his forecast of playoff football returning to the Windy City doesn’t feel like a hot take—it feels like a call to arms.

Only time will tell if his vision proves prophetic. But if the 2025 Chicago Bears do make the playoffs, you can bet the first person smiling will be No. 50—eyes wide, passion blazing, and vindicated by belief.