Vote in the Caleb Madness Bracket!

CHICAGO, ILLINOIS - NOVEMBER 23: Caleb Williams #18 of the Chicago Bears celebrates after beating the Pittsburgh Steelers 31-28 at Soldier Field on November 23, 2025 in Chicago, Illinois. (Photo by Justin Casterline/Getty Images) | Getty Images

It's March, and the madness is upon us.

Happy NCAA Tournament for those who celebrate, and we here at Windy City Gridiron have decided to celebrate in our own way.

As Bears fans, we thoroughly enjoyed all the highlights Caleb Williams provided over the past year. We decided to put together a bracket that you, the Bears fans, get to vote on to determine the best Caleb Williams play of the year!

We have picked 16 highlights from Caleb Williams from the season. We will hold the vote on Twitter/X and determine the winner as we work through the NCAA Tournament.

You will be able to cast your votes when the matchups are posted on my account, BillTZimmerman. But make sure you check out Windy City Gridiron throughout the tournament. We will post articles with the appropriate links every day there is voting!

The voting will begin on Monday, March 23rd. We will vote on 2 matchups per day, Monday through Thursday.

The week of March 30th, we will vote on two quarterfinal matchups each on Monday and Tuesday, and each semifinal matchup on Wednesday and Thursday.

The Caleb Madness Championship matchup will take place on Monday, April 6th.

There were so many Caleb Williams highlights to pick from; I am sure there are some that were left on the cutting room floor that you'll disagree with, but this is all for fun, so let's enjoy some great moments from the fantastic 2025 season.

And yes, I seeded these plays, but I am hiding the seeds so it doesn't sway anyone's opinion.

Here is a look at the bracket:

And here's a closer look at each play:

Jahdae Walker Game-Tying Catch vs Packers

This one has already gotten lost a little, thanks to what Caleb did not too long after this one, and some might say, Yeah, it's great, but he was wide open." That's true, he did finish wide open, but if you look at where Walker was when Caleb released the football, you'll realize that he broke open after the throw and was covered by two Packers at the release point. Williams saw it and delivered it, despite being under significant pressure.

CALEB WILLIAMS TD TO JAHDAE WALKER

GBvsCHI on FOX/FOX Onehttps://t.co/HkKw7uXVntpic.twitter.com/BWav3hisrZ

- NFL (@NFL) December 21, 2025

Caleb Threads the needle to OZ vs Packers

I think this is Williams' best throw of the season that nobody ever talks about. Perhaps it was because the Bears eventually lost this game, perhaps it was because it was only 1-yard out, but Williams rolls to his right, and throws a pass that somehow threads a needle right past a Packers defender and into the hands of a diving Olamide Zaccheaus.

Oh my O.Z. #ProBowlVote + @CALEBcsw#ProBowlVote + Olamide Zaccheaus pic.twitter.com/eNbZ8DNWj7

- Chicago Bears (@ChicagoBears) December 7, 2025

Game-Tying Heave to Cole Kmet vs Rams

The only way that could make this play better is if the Bears had ended up winning the game. Everything else about this is absolutely insane. It's so damn improbable. It still defies logic that it happened. Had the Bears won this game, I think this play eclipses The Catch" as the greatest non-Super Bowl play in NFL history.

NO WAY. CALEB WILLIAMS HEAVES IT ON 4TH DOWN.

LARvsCHI on NBC
Stream on @NFLPlus + Peacock pic.twitter.com/JJymsDhen2

- NFL (@NFL) January 19, 2026

Caleb catches a touchdown from DJ Moore.

From Caleb's side of things, this one isn't that exciting. The play is a beautiful design from Ben Johnson, and DJ Moore throws the football where it needs to be. It certainly isn't one of Caleb Williams' flashiest plays of the season, but I mean, he caught a touchdown pass. Are we just going to ignore it? Being Caleb had two receptions; you could have argued for the throwback from Tyson Bagent, but we'll go with the one that ended with six points.

DJ Moore throws a touchdown to Caleb Williams!

CHIvsCIN on CBS/Paramount+https://t.co/HkKw7uXVntpic.twitter.com/SK5g8iSNV9

- NFL (@NFL) November 2, 2025

Caleb Williams TD Run vs New York Giants

I think this was Caleb's best run of the season. Sure, he had crazier missed tackles, but when you watch this play and see the acceleration down the sidelines, considering the moment in the game, fourth quarter, Bears trailing, needing a touchdown to take the lead, Caleb rising to the moment easily puts this one in the top 16.

CALEB WILLIAMS FOR THE LEAD

NYGvsCHI on FOX/FOX Onehttps://t.co/HkKw7uXVntpic.twitter.com/pujzB6At9c

- NFL (@NFL) November 9, 2025

Flea Flicker to Luther Burden vs Cowboys

Watching this play live, you would have thought this play easily would have been one of the top 3 plays of the season, but by the end of the year, it was just part of the insanity that is Caleb Williams. You don't think about it much at this point, but this Bears game was critical to the Bears' turnaround. Who knows what happens if they fall to 0-3? Williams' coralling of the subpar pitch is what makes this one even more special.

BEARS FLEA FLICKER TD

DALvsCHI on FOX/FOX Onehttps://t.co/HkKw7uXVntpic.twitter.com/tMeMMgsWEy

- NFL (@NFL) September 21, 2025

DJ MooreOne-Handed Catch vs Ravens

This is the throw that I think was really impressive and gets lost in the story of the year. Perhaps it's because they lost this game, perhaps it's because DJ Moore didn't get out of bounds at the end of the play, but Williams spins with two guys in his face and fires this incredible ball across the field, and Moore makes an incredible one-handed catch.

This escape act and throw from Caleb Williams gets lost with all his other highlights this year. pic.twitter.com/krIrEqJBPD

- Bill Zimmerman (@BillTZimmerman) January 23, 2026

DJ Moore The Catch II" vs Browns

Caleb Williams' throw in this one mimicked arguably the most legendary throw and catch in NFL history, Joe Montana to Dwight Clark, The Catch." Moore snags the ball in the back corner of the end zone as the ball is just out of reach of a Browns defender.

I put together a side by side of The Catch (Montana to Clark, 1/10/82) and Caleb to DJ from Sunday (12/14/25). #DaBears#Bears#BearDown@CALEBcsw@idjmoorepic.twitter.com/YDIvWdoucg

- Ryan Droste (@ryandroste) December 16, 2025

Game Winner to DJ Moore in OT vs Packers

We certainly thought this was going to be the throw of the year, but at the time, we didn't know what Caleb Williams had in store for us in the playoffs. Tom Brady called this his favorite throw of the year, a brilliant throw to Moore in the perfect spot that tops off an incredible come-from-behind victory against the Bears' rivals in overtime.

CALEB WILLIAMS TO DJ MOORE

BEARS WIN pic.twitter.com/3ShtuowNYm

- NFL (@NFL) December 21, 2025

Caleb escapes Brian Burns' sack, runs for 1st

There are so many Houdini acts from that year, you need one to represent what Caleb did in the pocket. Caleb does an incredible job escaping the grasp of Brian Burns, one of the best edges in the NFL, scampers towards the sideline, avoids a tackle from Kayvon Thibedoux, and runs for the first down.

If you want to enjoy a compilation of Caleb avoiding sacks, you should check out this video here.

Brian Burns (6'5", 250) is tied for the #NFL lead with 11 sacks, but #Bears QB Caleb Williams shook off his sack attempt on this play, then ran through the tackle from Kayvon Thibodeaux (6'5", 258) for a 5-yard gain on 3rd and 4. pic.twitter.com/SMDpxNKYJU

- Lester A. Wiltfong Jr. (@wiltfongjr) November 11, 2025

Cole Kmet ices game vs Eagles

It's funny how effortlessly Williams rolls to his left and still manages these throws. The Bears were frauds" in everyone's minds until this game. The Bears went into Philadelphia and dominated the defending Super Bowl champions. This throw puts the game away as Williams rolls left and lofts a fadeaway, soft catchable ball that only can fall into the hands of Cole Kmet.

CALEB TO KMET. WHAT A THROW.

CHIvsPHI FREE on Prime Video
Also streaming on @NFLPluspic.twitter.com/fcyQ9JLQCj

- NFL (@NFL) November 28, 2025

DJ Moore Go Ahead TD vs Packers, Wild Card

This was set up beautifully by Ben Johnson, who used a bunch set all game and set up the Packers DBs to bite at the line of scrimmage and released DJ behind them. Caleb has a nice pump fake to freeze the defender, and DJ breaks wide open. This isn't one of Caleb's flashier players, but it's a solid throw and, you know, leads to the Bears beating the Packers in the playoffs.

Bears after halftime vs. Packers

Wild Card: 28 points
Week 16: 22 points
Week 14: 18 pointspic.twitter.com/nDIHceRTsY

- Underdog NFL (@UnderdogNFL) January 11, 2026

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.

Caleb "Houdini" Williams

: NBC pic.twitter.com/TqAtQQzDp4

- Chicago Bears (@ChicagoBears) January 19, 2026

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.

COLSTON LOVELAND 58 YARDS! WOW! pic.twitter.com/JRZOV8ih3J

- NFL (@NFL) November 2, 2025

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.

CALEB WILLIAMS TAKES IT IN HIMSELF

Watch Vikings-Bears on ABC, ESPN and the ESPN App https://t.co/CgLyUok6D9pic.twitter.com/k6n9L5vWD9

- ESPN (@espn) September 9, 2025

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.

Caleb Williams really made this throw on 4th and 8 pic.twitter.com/lVKFf5p6yH

- NFL (@NFL) January 11, 2026