Charlie Cummings gives insight into his favorite Josh Giddey player prop bet for Wednesday’s Trail Blazers vs. Bulls matchup.

After a rocking 5-0 start, the Chicago Bulls have come back to earth. Josh Giddey’s injury has contributed to this regression, but now their top creator is back in action. Tonight’s game against an injury-riddled Portland Trail Blazers team is a chance for Giddey and the Bulls to get back on track.

The Bulls are 4.5-point road favorites on DraftKings Sportsbook. They’re priced at -175 on the Moneyline, while the Blazers are +145 underdogs. The total for this game is set at 242.5 points. Let’s get into my favorite Josh Giddey prop bet for this Bulls vs. Blazers showdown.

Best Josh Giddey Player Prop for Bulls vs. Trail Blazers

Portland comes into this game with three of its best perimeter defenders already ruled out. Matisse Thybulle and Blake Wesley won’t be present for this game. Jrue Holiday didn’t play last night and has been ruled out with a calf injury. That leaves Toumani Camara with the job of containing Giddey.

Usually, that’s a big plus for the Blazers. The emergent Camara was an All-Defense selection last year and has excellent tools for perimeter containment. But, so far, he’s struggling to follow up last season’s dominance. Giddey’s perimeter creation is trending up, and there are more pressure points the Bulls can use now that Coby White is healthy again.

COBY WHITE GETS THE TIE-UP.
COBY WHITE WINS THE TAP.
COBY WHITE TIES THE GAME.

In his season debut… Coby White absolutely takes over to force double-overtime 🤯 pic.twitter.com/eNhTyJLD8X

— NBA (@NBA) November 17, 2025

Usually, containing Giddey and White on the perimeter would be no problem for Portland. But as the injuries continue to mount, the Blazers are going to need to make some tough choices.

The best they can hope for is to take away Giddey’s playmaking and force him to beat them as a scorer. I expect Giddey to oblige on the drive and get up a handful of threes. It’s not the best strategy for Portland, but it might be the only one they’ve got.

Best Josh Giddey Prop Bet: 21+ Points Scored (-102)