The final 19.8 seconds of regulation between the Bulls and Raptors was a chaotic masterpiece

A very exciting if not exactly polished game of basketball was played in Chicago on Friday between the hometown Bulls and the visiting Toronto Raptors. At various points in the game, both teams managed to overcome deficits of at least 17 points. The Bulls did so in the final five minutes of regulation and snuck away with a 104-103 overtime victory on an Alex Caruso 3-pointer with 2.1 seconds to go.

If you’re looking for the positive elements of that thriller, most highlight packages will offer them. We’re going to take things in a different direction and zoom in on the particularly chaotic sequence that sent the game to overtime. The final 19.8 seconds of regulation saw the Raptors choke away several opportunities to win the game only for the Bulls to blow multiple opportunities of their own to steal this thing in regulation. If you’re here for high-quality basketball played between two contenders, you’ve come to the wrong place. To those who remain, join me as we venture through the most bizarre 20-second sequence of this young NBA season.

Our story begins as so many late-game disasters do — with a frantic inbounds pass. Leading by three at 91-88, the Raptors just needed to get the ball in bounds and get fouled. Make a couple of free throws and they’re walking away with the victory. But with no clear pass available to Pascal Siakam, Scottie Barnes runs into the backcourt to give him an outlet. And this is where things get funky, because for the life of me, I have no idea how Barnes loses this ball.

Alex Caruso definitely makes an aggressive play for the ball, and Torrey Craig is looming in the background, but if you pause at the 18.9-second mark, you can clearly see Barnes has firm control of the ball with Caruso on the ground. Yet when he makes the move to pass the ball to Dennis Schroder, the ball just sort of slips away from him. Chicago comes up with it. DeMar DeRozan makes a layup and gets fouled in the process. DeRozan is an 84% free throw shooter for his career. Surely, he’s about to tie the game, right? Not so fast my friend.

What follows DeRozan’s miss is a somewhat chaotic sequence in itself. Caruso rebounds and gives DeRozan a chance to take the lead with another layup, but he misses and Chris Boucher grabs the rebound. Suddenly the officials whistle the play dead. They call goaltending on Barnes to give Chicago the one-point lead, and then immediately signal for a review. In the end, that goaltending call wound up hurting the Bulls. Not only was it overturned and possession awarded to the Raptors, but because the play was whistled dead, the Bulls wouldn’t have a chance to force a turnover or jump ball against Boucher, who is on the ground fighting for possession with Zach LaVine.

What a relief for the Raptors, you’re probably thinking. They escape the possible three-point play from DeRozan that they never should have allowed and the possible putback generated by their own poor rebounding. Surely they’ll make the most of this gift from the basketball gods? I’m sorry, Toronto readers. This is not that kind of story.

Siakam does his job on the next inbounds play. He is fouled quickly and makes both free throws to restore Toronto’s three-point lead. This is where Toronto’s dominant perimeter defense should come into play to finish off the victory. Instead, we circle back to Boucher, who may not have read the scouting report closely enough before this one, because he falls for DeRozan’s favorite trick. Raptors fans could only look on in horror as DeRozan pump fakes Boucher into the air only to lean in and draw a three-shot foul.

DeRozan has already missed one game-tying free-throw, but folks, I promised you a chaotic masterpiece and I’m going to deliver a chaotic masterpiece, because after making his first two attempts and pulling the Bulls back to within a single point, one of the NBA’s premier free throw merchants misses again, front-rimming what should have been his game-tying bucket. He knew it, too, because as soon as he released the ball, he immediately bolted in for the rebound. He got it, but he clearly left early.

The refs whistle him. Toronto ball with 3.5 seconds left. Man, what an escape for the Raptors. Just pass the ball to a man in a black jersey that is within the white lines and you might be able to run the clock out without even needing to draw a foul. By now you’ve probably realized that isn’t what’s about to happen.

Siakam shoves Caruso to the floor and gets whistled for the offensive foul. The Bulls have life! After blowing two chances to tie the game at the line, they’ll have one winner-take-all shot with 3.5 seconds left in the game. But this is still the vaunted Toronto defense we’re talking about here. One stop in under four seconds? That’s doable. Just as long as they don’t commit another … oh boy.

That’s right loyal reader, the Bulls bit on another DeRozan fake. This time, it’s a desperate Barnes flying in from the top rope to whack DeRozan and give the Bulls a chance to win it. DeRozan is human. He might miss one big free-throw. Even two is realistic. But no six-time All-Star that is widely regarded as one of the most clutch players in the NBA is going to miss three game-changing free throws in under 13 seconds. That would never happen. Except it did.

So let’s recap. In 20 seconds, we witnessed two of the worst turnovers the Raptors will commit all season, a potentially game-changing whistle and review, and three separate missed game-winning free throws from one of the best free throw shooters in the NBA. I defy you to find a more bizarre, mistake-riddled sequence of professional basketball in recent memory. Both teams served the other victory on a silver platter. Both teams rejected the generous offer and decided to play it out the hard way.

Eventually, someone had to win the game. Caruso did so on this 3-pointer.


— Chicago Bulls (@chicagobulls) October 28, 2023
The Bulls earned their first victory of the year and sidestepped the glorious possibility of two players-only meetings in two games. But that’s not how we’ll remember this game. We’ll remember it for the performance art piece that was the final 20 seconds, perhaps the sloppiest end of a basketball game we’ll see all season.

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