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Chicago Bulls vs. Portland Trail Blazers prediction, pick on Wednesday 11/19/25

Chicago Bulls vs. Portland Trail Blazers prediction, pick on Wednesday 11/19/25

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By: Bryan Armetta

November is a time of uncertainty across the NBA. Hot starts and cold streaks abound, making it difficult to determine whether clubs are ‘for real’ or not. No two teams exemplify this better than the Bulls and Trail Blazers. Chicago, following a 5-0 start, has dropped six of their last eight games. Portland, despite off-court drama and a brutal early schedule, has stayed afloat at 6-8.

Which of these squads has the edge entering tonight’s inter-conference showdown? Below is my prediction and pick for Wednesday’s game between the Chicago Bulls and the Portland Trail Blazers.

The Bulls are 2.5-point favorites (-115) over the Trail Blazers on DraftKings Sportsbook. Portland is favored at -142 on the moneyline. The total is set at 244.5 points.

Bulls vs. Trail Blazers prediction, preview

In a league full of enigmas, Chicago stands out. Is this the group that took the NBA by storm, or the one that’s gone 2-6 over its last eight appearances? The true answer likely lies somewhere in between. It’s easy to see why most fans and analysts would dismiss the team as a contender. For years, the Bulls have been an Eastern Conference play-in staple, finishing with a winning percentage just under .500. Still, this squad has managed to win games thanks to its depth. Seven different players are averaging double-digit points this season.

One name that could give Chicago a spark is Coby White. A calf injury has kept the guard out of commission for nearly a month. However, he posted 27 points and eight assists over 30 minutes during his season debut on Sunday vs. the Jazz. The Bulls have been carried by the all-around play of Josh Giddey. Through 11 games, the Aussie is averaging 21.8 points, 10.3 rebounds and 9.4 assists. A date with the up-tempo Blazers should lead to another stat-stuffing performance for the 23-year-old.

Granted, Portland has shown massive improvement when it comes to guarding the perimeter. Opponents are only knocking down 12.0 three-pointers per game, the fifth-lowest mark in basketball. However, offseason acquisition Jrue Holiday (calf) might miss his second straight game. In addition, forward Jerami Grant is battling an illness. Losing either player would be a serious blow to the Trail Blazers, on the second leg of a back-to-back.

As previously alluded to, Portland plays at the NBA’s third-quickest pace on offense (102.8). That’s led to plenty of scoring from Deni Avdija and Shaedon Sharpe. Together, the two have combined for 48.1 points per game; that’s over 1/3rd of the team’s total output. However, the Blazers are the anti-Bulls; only six players are averaging more than 6.0 points per game. Rebounding has been a bit of an issue recently as well. That could play into the hands of Chicago center Nikola Vucevic, a double-double machine.

Bulls vs. Trail Blazers pick, best bet

On paper, Portland has a more talented roster compared to Chicago. However, the visitors deserve to be favored tonight due to their depth. On a back-to-back, with Grant and Holiday potentially out, the Blazers are short-handed. In comparison, their opponents will have fresher legs all game. A deeper Bulls squad should eke out a West Coast win on Wednesday.

Best Bet: Bulls -2.5 (-115)

Bryan Armetta is a New York-based writer that has spent over eight years in sports media. Working for DraftKings since 2024, he currently serves as a writer, editor and analyst for all things sports and pop culture. Bryan specializes in MLB, NBA, NFL, college sports and entertainment content. Prior to his time at DKN, he worked for MLB Network, NHL Network and SiriusXM Sports.
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.