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Chicago Bulls vs. Toronto Raptors prediction, pick for Wednesday 10/21/26

Chicago Bulls vs. Toronto Raptors prediction, pick for Wednesday 10/21/26

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By: Charlie Cummings

It’s time to get into full swing for the season’s first full NBA slate. The Chicago Bulls, fresh off an offseason makeover, will travel to Toronto for an important reunion. Kawhi Leonard will play in a Raptors jersey for the first time since winning Game 6 of the 2019 Finals. Now championship expectations are back in town, and a matchup with these Bulls is a good place to start. We’ve got debuts all over to enjoy, so let’s get into this matchup.

The Raptors enter as 9.5-point home favorites with -425 moneyline odds on DraftKings Sportsbook. The Bulls are +330 underdogs, with the game total set at 236.5 points.

Bulls vs. Raptors Preview

Last season felt like a band-aid being ripped off for Chicago. After three straight seasons in the play-in tournament, Chicago punted on much of its roster, trading Nikola Vucevic and Coby White to reset. The lottery rewarded them with the fourth overall pick in this past draft, and they snagged talented big man Caleb Wilson from UNC. With a true blue-chip prospect under their belt, new head executive Bryson Graham felt comfortable making some improvements.

Norm Powell was the biggest addition of them all. Last season, in his lone campaign with the Miami Heat, Powell became the fourth-oldest first-time All-Star at 32. He remains one of the league’s best high-volume three-point shooters and was brought in as an off-ball complement to Josh Giddey. They also acquired Nic Claxton in a salary dump, and if he’s healthy and motivated, they got a starting center for free. With the addition of Buddy Hield to boot, Chicago added a lot of veterans to lift up their young core.

Josh Giddey has been the centerpiece of their youth movement so far, but before long, it will be the Caleb Wilson and Matas Buzelis show. After a strong rookie campaign, Buzelis had an excellent sophomore season, solidifying his status as a franchise cornerstone. Wilson, an elite defensive prospect, lit up Summer League with his scoring and looks like a two-way impact player from day one. Those two will be an exciting forward tandem. They also have fellow rookie Dailyn Swain, Noa Essengue, and Leonard Miller competing for minutes; if one or two of them pop, head coach Tiago Splitter won’t have a shortage of productive, athletic wings.

The Toronto Raptors are what the Bulls hope they could be in a few years. Last season, Toronto’s energetic defense and functional size pushed them from the lottery into the playoffs, and they nearly upset the Cleveland Cavaliers in the first round. Scottie Barnes has come into his own as a two-way star, and they got excellent production from RJ Barrett and Collin Murray-Boyles to lead a deep, talented team.

They wasted no time capitalizing on this success. Brandon Ingram, who wasn’t quite what they’d hoped he would be, was the sacrificial lamb in a trade for Kawhi Leonard. Fresh off another elite season, Leonard steps into the top-scoring role on a team deep with offensive talent. The team already has an exceptional defense, so Kawhi can contribute defensively in spurts and lock it down the stretch. It’s tough to imagine a lineup with more two-way appeal than Immanuel Quickley, Barrett, Leonard, Barnes, and CMB.

This matchup centers on Chicago’s offense versus Toronto’s defense. The Bulls will want to get out and run, shoot a ton of threes, and get their opponents on the back foot. Toronto excels at setting the defensive tone, but it’s easier said than done against a team trying to move at a million miles per hour. If they can keep things under wraps, the Raptors will find plenty of space against a jumbled Bulls defense.

Now that we know these two teams a bit better, who will take home the win?

Bulls vs. Raptors Pick, Best Bet

I feel confident in the Raptors as a season-long bet, but teams making big changes don’t always hit the ground running. It may take only a few games for them to find cohesion, but that’s an edge for the Bulls you can’t ignore. I’ll roll the dice on Chicago pulling off a road upset.

Best Bet: Chicago Bulls Moneyline (+330)

Charlie Cummings is a Bay Area-born writer living in Denver. A basketball junkie, he specializes in NBA and WNBA content, but also dabbles in soccer, baseball, football and hockey. You can find him on Twitter @klaytheist11 where he’s posting through it on a daily basis.
Disclaimer

I am a promoter at DraftKings and am also an avid fan and user and may sometimes play on my personal account in the games that I offer advice on. Although I have expressed my personal view on the games and strategies above, they do not necessarily reflect the view(s) of DraftKings and do not constitute a representation that any particular strategy will guarantee success. All customers should use their own skills and judgment in building lineups. I may also deploy different players and strategies than what I recommend above. I am not an employee of DraftKings and do not have access to any non-public information.