Trail Blazers Won't Have to Try to Get Into Cooper Flagg Sweepstakes

The Trail Blazers need “the guy.”

Scoot Henderson’s uneven rookie season and Shaedon Sharpe’s second year being cut short by injury were two reminders that the Blazers’ rebuild still doesn’t have its foundational star, its Anthony Edwards or Shai Gilgeous-Alexander that they can definitively say they’re building around.

One of those guys—Cooper Flagg—is at the top of the 2025 draft class. People who know a lot more about this stuff than I do say there are at least a few more who could also be that good.

It’s the opposite of this year’s draft, both in talent and in stakes. When the Blazers fell back three spots in the lottery, from the fourth-worst record in the league to the No. 7 overall pick, the top decision-makers were unworried. Evaluations of the 2024 draft class were so all over the place that they thought there was a good chance they’d still be able to get who they wanted.

It ended up playing out just like that: while Joe Cronin has not directly confirmed it, I have a strong suspicion Donovan Clingan was the highest-ranked player on the Blazers’ draft board from the start, and he fell to them at the seventh pick.

Next year, more than most years, it would be helpful if Portland was one of the bottom three teams in the standings, which comes with a 14 percent chance of landing Flagg at No. 1 overall.

The good news: this team won’t have to do anything extra to be right there.

If the goal is ping-pong balls, the basketball gods (or, more accurately, the league’s schedule-makers) did the Blazers a solid.

According to Positive Residual, Portland has the NBA’s toughest strength of schedule for the upcoming season. A closer look reveals just how brutal it truly is.

For one thing, 27 of their first 29 games come against Western Conference teams, at a time when the west is more competitive than it’s ever been. The Blazers are the only one of the 15 teams going into the season with a path already charted for the bottom. Utah will probably join them in the end, but they extended Lauri Markkanen earlier this month rather than trading him, so they’ll at least begin the season trying to compete before pulling the plug. Everyone else—including last year’s lottery teams like San Antonio, Houston and Memphis—wants back in the postseason.

The Blazers also have five of their 13 back-to-backs in the first month of the season, with 16 of their first 18 games being part of three-games-in-four-nights stretches, all against that Western Conference gauntlet.

In other words, you don’t have to worry about them accidentally winning too many games in the early part of their season, when they’re at their healthiest and hungriest. They can play as hard as they want, and everyone can be healthy and available, and Chauncey Billups can play everyone their full allotment of rotation minutes without any phantom injuries, and they’re still going to lose a lot because they’ll be playing a team with more talent just about every night, and doing it without a lot of rest.

They’ll be lucky to get to double-digit wins before the calendar turns to 2025.

By then, the field of competition for this game of “Capture the Flagg” will be clearer. You can write Brooklyn and Washington down in Sharpie right now. Detroit, Chicago and Toronto could get in the mix, but like Utah, they’re going to try to be respectable before leaning into the tank. By the time we get to March and April, the five-rookie starting lineup Portland trotted out last spring could be the norm for all of these teams. That’s how good team front-office personnel think Flagg is, and how good a few of the consolation prizes might be.

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I’m far from a gambling expert—never placed a bet in my life—but after seeing the schedule, the Blazers’ over/under being set by most sportsbooks at 21.5 wins for this season makes a lot of sense. They’ll be better than they were last year, with better health, the arrival of Clingan and Deni Avdija and expected improvement from Henderson and Sharpe. But their competition will also be better and their road will be tougher.

Maybe Cronin will have a fire-sale at the trade deadline. Maybe he won’t. Jerami Grant feels like a prime candidate for a playoff team to talk themselves into as this year’s P.J. Washington midseason impact trade. Depending on how Henderson develops, maybe the Blazers look at moving Anfernee Simons.

Trading one or both of their two best players at the deadline wouldn’t hurt the season objective of getting as high of lottery odds as possible. But if there’s one thing the Cronin-Billups era of the Blazers has proven over the past three seasons, it’s that if they need to lose a lot of games, they can find a way to do it, no matter who is or isn’t in the lineup.

This year, the goal for the season is clearer than it’s ever been. The Blazers’ schedule and the bloodbath at the top of the Western Conference mean their path to get there is clearer than it’s ever been, too.