The Portland Trail Blazers have spent much of the 2025-26 season coping with injuries to key players. That’s a sad development for the franchise as a whole, but an opportunity for all the “next men up” on Portland’s roster. No players have embodied that spirit more than Caleb Love and Sidy Cissoko, Portland’s most prominent two-way contract recipients this season.
Appreciating the contributions of both men, one of our Blazer’s Edge Readers is asking a question about their potential. We’ll tackle that
in today’s Blazer’s Edge Mailbag.
Dave,
Sidy Cissoko or Caleb Love? Which of them do you keep and why? The Blazers are going to have to make this decision pretty soon since they’re 2-ways right? I’m curious about which one you like best.
Niles
I mean, both? And neither.
But before we get into that, if you like what we do here, can you please head over to this website the Blazers have set up and donate a couple (or a few) tickets so kids in need in the Portland area can see the Blazers play the Hornets this March? We need something uplifting to unite us in these times. This can be one of those things. People who work in underserved communities are writing and asking if they can take their students to our Blazer’s Edge Night event. We want to tell them yes, but donations are a little behind. Can you help us out? Read all about the event here.
Now back to the question. You’re making me choose between Love and Cissoko? That’s difficult, but apt.
As you mention, there could be some mildly interesting action coming up. By rule, NBA two-way contract players can only play in 50 games for their parent clubs each season unless the franchise converts them to a regular contract. The Blazers could do that with either or both, making them regular roster members, but Portland is already carrying a full slate of players. Cissoko has played 36 games so far this year, Love 33. If nothing changes, they’ll only be available for 35-40% of the remaining schedule.
Portland has options.
One would be to live with those restrictions, hoping that injury returns would lessen the need for their two-way players. Getting Scoot Henderson and Jerami Grant healthy would sure help.
Straight up waiving someone to convert a two-way player would be tricky, but doable. The margin is razor-thin; the Blazers will be eyeing the luxury tax line which they currently abut (or for those under 20, agyatt). Basically they have room to waive one player making minimum and convert one two-way player without going over the threshold. They can’t convert both players without getting penalized financially.
Another option would be to make trades, freeing up a roster spot for one or both. Or Portland could convert one or both and include them in a trade.
So yeah, there’s a possibility that your theoretical choice becomes a live option.
As for my personal choice, I like each of them for different reasons.
Cissoko is the more polished player, the better two-way guy (in the court-play sense, not the contract sense). His body is sturdy and he’s got good court awareness. Of the two, he’s the basketball aficionado choice.
Love is the offensive daredevil, the guy who will pull out games for you with his firepower. He’s got rare confidence and shot-separation ability. With the style he plays, you’d think he was a lottery pick instead of a non-drafted late signee. You can’t teach that. He’s the “out of your seat” fan guy.
If we were talking cars, Love would be the shiny chassis and engine, Cissoko the transmission and differential and all the underpinnings that make the vehicle run. In that sense, they’re both valuable, theoretically necessary.
But why are they necessary? Again, it’s because of injuries. For the 2025-26 Trail Blazers they’ve been indispensable. Does that put them on par with all other NBA players? Would they be playing similar roles on the Houston Rockets, Phoenix Suns, or San Antonio Spurs?
The answer to that question is clearly no. That’s not a slight to either player. Their accomplishments so far are exciting and admirable, but that’s also accounting for curve-grading them as relative unknowns on a franchise deeply in need of warm bodies and able to give them minutes without consequence.
On an absolute scale, we’d have to consider more factors. Love shoots 33% from the three-point arc on average, somewhere around 37% over time at his zenith. And he’s shooting under 40% from the field. Cissoko is 13th on the team in per-possession scoring, 15th in rebounding, 10th in assists, and 4th in fouls. He also shoots under 40%. None of those numbers are good, let alone special.
I love the way Love and Cissoko have stepped up this season and filled minutes. I can also find players like Love and Cissoko on pretty much every team in the league. Their contributions are a testament to their personal hard work and growth. Those contributions also show that everybody who plays basketball anywhere near an NBA level is very, very good at this sport and, given the chance, can do something with that ball. Can they do it better than all the other people at the pinnacle of the game? That’s the real question in an ultra-competitive league. We’ve seen nice flashes from both players. We haven’t seen that question answered conclusively, or maybe at all.
The answer to your hypothetical is that I’d like to keep both players on the basis of their dedication, skills, and what they’ve meant to the team this year. It’s more than could be expected. But they’re doing all that in fractured lineups on a team winning 46% of their games. Those things are related. And as long as that remains true, the choice between them probably doesn’t matter much.
If you made me choose just one of them right now, I think I’d go with Love. Cissoko’s base is broader but Love’s ceiling is higher. Both have room to blossom, but chances are neither one of them will end up as a significant contributor long-term. If I’m going to take a risk, it’s on the guy who has a (at least small) chance to become my team’s first- or second-leading scorer rather than a guy who’s going to be steady as my 7th-9th man, simply because I can find nice utility players plenty of places. But if you’re asking who I want to put in the lineup tomorrow, I’d favor Cissoko because the Blazers need someone to hold the line and support the cause while their more accomplished players try to win the game.
Either way, I suspect that the Blazers are going to look to make a trade over the next three weeks that solves this problem partially. If they can’t pull that off, look for them to convert one of their two-way players and live with the contract limitations of the other. Which one they choose depends on their priorities, but given the makeup of their roster—and admitting that I know nothing of the way they’re thinking behind closed doors—I’d expect them to keep Cissoko on the main floor and let Love develop in the G League.
Thanks for the question! You can always send yours to blazersub@gmail.com and we’ll try to answer as many as possible. And don’t forget to get tickets so some Portland-area kids can have a fantastic spring!
