Last season, the Trail Blazers had major success with their two-way contract spots. Sidy Cissoko and Caleb Love broke through as important contributors in the midst of injuries, helping the team stay competitive and eventually reach the playoffs. Cissoko earned a conversion for his efforts, the ultimate prize for a two-way guy, and will be on a standard deal competing for a backup spot moving forward.
What about 2026-27? Can Portland make more magic happen with their fringe players next season? Here are all three of their current two-way contract players ranked by how likely they are to surprise people and become rotation pieces in some capacity:
No. 3: Chris Youngblood
Youngblood has a shot to get his number called next year because his one NBA skill is one that the Blazers are desperately trying to improve: three-point shooting. The 6’4” wing is rock-solid off the catch and on the move, making him an effective spacer who wouldn’t step on the toes of Deni Avdija, Ja Morant, and Damian Lillard.
The ceiling with Youngblood is pretty low because he doesn’t do much else besides shoot it. Unfortunately, his floor is also low. He played 174 minutes across 32 games for the Thunder as a rookie, and in that time, he made little to no impact. He wasn’t locked in from deep, going just 31.4% from beyond the arc, which made him virtually invisible out there.
Youngblood’s shooting pedigree could get his foot in the door, but the odds of him rising the ranks and becoming something solidified are slim.
No. 2: Jayson Kent
Kent is a total wildcard here. His journey to joining the Blazers’ roster was an inspiring one— he went undrafted out of Texas in 2025 and carved his place with the Rip City Remix through local tryouts. Now, he’s in the NBA, and the question is, can he stick?
As an athlete, Kent is clearly NBA-caliber. He can get up for exciting slams and guard his yard defensively. His chances in the league will hinge on how he develops his offensive game. In college, he was a 29.4% three-point shooter across five years. But, as a rookie in the G League, he shot 39.5% on respectable volume.
If the jumper is for real, Kent could sneak his way onto the floor for Portland. After all, their backup forward spots are almost completely up for grabs. But, if he can’t find a way to consistently score, he’s going to be fighting a serious uphill battle.
No. 1: John Tonje
Tonje is one of the top candidates for a two-way contract breakout in the entire association. As an individual player, he’s more polished and refined than most of his peers. His role as a 3&D wing is definite, and he has the talent to excel within it.
Considering his strengths as a shooter and overall off-ball guy, Portland is a fantastic situation for him. He’s exactly the type of small forward they need. If the 2025 second-round pick can prove he can hang on an NBA court, it could become tough for Micah Nori to keep him off it.
Overall, this is an intriguing crop of two-way players for the Blazers. If they invest in these guys, they could become a better team.
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