The Portland Trail Blazers weren’t expected to be anything more than a rebuilding project this season, but thanks to some emerging young talent and scrappy play, they’re firmly in the mix for the 2025 Play-In Tournament.
Following Wednesday’s upset win over the Memphis Grizzlies, Portland sits 2.0 games back from both the Dallas Mavericks and Phoenix Suns for the final play-in spot.
Of course, all the hard work that put Portland in this position has also reduced its chance of landing a top pick in June’s draft. That’s the “price” you pay for not giving in to expectations.
But here’s a question: What if the basketball gods reward Rip City’s refusal to tank in a bigger way than with a play-in berth? What if the ping-pong balls say screw the Washington Wizards and give Portland the No. 1 pick in the 2025 NBA Draft anyway (assuming they don’t make the playoffs)?
The winner of this year’s lottery, whoever it is, will draft Duke star Cooper Flagg, the highly touted forward who’s also the headliner of the 2025 NCAA Tournament. But as history has shown, the lottery offers no certainties. Just ask the Detroit Pistons, who slipped out of the top spot the past two seasons. Or conversely, the Atlanta Hawks, who landed the No. 1 pick in 2024 despite owning just the league’s 10th-worst record and 3 percent odds for the top selection.
Anything can happen, so let’s get wild for a second. Let’s imagine what it would look like if Flagg landed in Portland. And let’s look at what this top prospect really brings to the table.
Flagg’s Pro Comparisons and NBA Outlook
Cooper Flagg is the kind of prospect scouts dream about. At 6’9” with elite defensive instincts and a versatile offensive game, he has drawn comparisons to some elite two-way wings.
A common Pro Comp is Andrei Kirilenko. It’s an easy comparison to make when Flagg impacts the game in every facet—scoring, passing, rebounding, shot-blocking, and perimeter defense.
Flagg, though, likely has a higher superstar ceiling and a more complete offensive game than Kirilenko. That’s why some have also seen shades of Jayson Tatum in Flagg’s future.
Flagg’s biggest strengths are his defensive versatility and high basketball IQ. He should be able to guard multiple positions at the NBA level (and play multiple positions), protect the rim, and help anchor any defense. And it should be noted that his motor is never in question.
Offensively, Flagg has a developing three-point shot, a smooth handle for his size, and great court vision, making him easy to project as a point-forward whether he starts at the 3 or the 4.
As you see in the video above, he can also turn defense into offense with the best of them and in highlight fashion.
Overall, it’s difficult to picture a roster Flagg wouldn’t fit in with on Day 1.
Any Red Flags?
Flagg’s biggest question mark will be strength and physicality. That’s typical for most entering the league, and it’ll be true for Flagg, who won’t turn 19 until two months into his NBA career.
However, when Flagg debuts in the NBA, it won’t be the first time we’ve seen him size up against NBA talent. It was during 2024 pre-Olympics gym runs when a then-17-year-old Flagg had NBA Twitter buzzing after his scrimmage with Team USA.
I haven’t read a single scout’s take that says we need to worry about Flagg’s long-term physicality.
Fit With the Trail Blazers
One thing to get out of the way: There is no debate here about Team Fit vs. Most Talented. If you have the No. 1 pick, you take Flagg, and you don’t think twice about roster overlap.
Flagg’s presence would immediately give the Blazers a dynamic defensive piece to pair with their promising young core. Jerami Grant’s future is uncertain with the team (not to mention Robert Williams, Matisse Thybulle, and more), and essentially swapping Grant out of the starting lineup for Flagg is a no-brainer.
Toumani Camara and Deni Avdija are important parts of the equation, though. Do you make Camara, your blossoming two-way stud, a long-term sixth man? If not, does Flagg start at 3 in favor of Avdija?
Barring roster moves beyond a Grant departure, positional overlap might exist. But the good news would be that a Deni-Toumani-Cooper trio would have the versatility to eventually, if not immediately, mitigate any redundancy.
How Good Would the Blazers Be With Flagg?
With the current version of the Trail Blazers knocking on the Play-In Tournament door at least one year ahead of schedule, betting on Portland to make the playoffs in Year 1 with Flagg wouldn’t be ridiculous.
Of course, you wouldn’t be air-dropping Flagg onto this exact roster. Most players are under contract through at least next season. But I also have a feeling general manager Joe Cronin would find a way to create a market for his assets if he landed a building block in Flagg, e pedi g the final stage of the rebuild.
Short-term, adding Flagg to any similar version of this roster would be a win. If you thought the Blazers were fun and had that dog in them this season, you’d be in for a treat next year.
Long-term, it’d be the type of move that lets you finally breathe easy thinking about the future.
Either way, building a roster around Flagg and whoever else the team thought worked with him would be the ultimate ein both now and looking ahead.
Would it bring a championship to Portland? There’s no way to say. But I have a feeling everyone in Rip City would be willing to find out.
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