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Caleb Madness Bracket: Vote on the day 4 matchups

· Yahoo Sports

CINCINNATI, OHIO - NOVEMBER 02: Colston Loveland #84 of the Chicago Bears scores a touchdown during the fourth quarter against the Cincinnati Bengals in the game at Paycor Stadium on November 02, 2025 in Cincinnati, Ohio. (Photo by Dylan Buell/Getty Images) | Getty Images

We have reached the final day of first-round matchups in the Caleb Madness bracket, where you, the Bears fans, vote on Caleb’s best play of 2025. So far, we know that the Elite 8 matchups will feature Jahdae Walker’s game-tying catch against Green Bay and the Cole Kmet TD heave against the Rams. We will see the Luther Burden flea flicker against the DJ Moore “The Catch II” against the Browns. Our third matchup will be DJ Moore’s go-ahead score against the Packers in the Wild Card game against another DJ Moore play, the epic game-winning catch against Green Bay in overtime.

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Let’s see what two plays advance today to round out the Elite 8.

Caleb’s Houdini escape vs LA Rams VS Colson Loveland game winner vs Bengals

This is another one where I think the voting could get interesting. We are voting on Caleb’s best play. The Loveland play was a phenomenally timed throw, but a lot of the magic happened afterwards, thanks to Loveland. The Caleb escape and run, which resulted in a big first down, was all Caleb from start to finish. Let’s look at the four plays.

Houdini escape, first down run vs Rams

We needed a couple of Caleb’s escapability plays in this tournament. This one also makes the list because of the importance of the game and the play. With the Bears trailing by 7 in the fourth quarter, Caleb escapes pressure, somehow works his way through about 4 defenders, and takes off for a 26-yard gain and pushes the ball into Rams territory. Maybe not his greatest escape, but arguably the most important in a big moment.

Colston Loveland Game Winner vs Bengals

I felt this throw needed to be recognized because of the precise moment he released the ball. It’s not his most athletic throw of the season, but it’s the timing of the throw. Williams hits Loveland in a sea of Bengals, where if he throws it a tick earlier or a tick later, the result would have been an incomplete pass or an interception. When you consider the pressure with less than 30 seconds to go, Williams needed to deliver a strike, and he did just that.

To vote on this matchup, you can do so here:

Let’s look at our next matchup:

Caleb Williams rushing TD vs Vikings

The opening game of the season may not have finished the way anyone would have wanted, but the Bears’ first touchdown of the season was just foreshadowing of what was to come. Williams flashed his pocket presence and mobility, dancing in the pocket, showed his speed as he sprinted outside and down the sideline, and showed his power as he broke a tackle and crossed the goal line.

Rome Odunze jumpman throw on 4th down vs Packers, Wild Card Weekend

Don’t worry, we didn’t forget this one. If this ball falls incomplete, the Bears’ season is over. But Williams on 4th down, giving us a glimpse of the Air Jordan logo and dropping this one into Rome Odunze’s lap as 4 Green Bay Packers surround him was one of the best throws in the history of the league, and yet, somehow, he tops it one week later.

And to vote on the final first-round matchup, you can do so here:

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