If you've spent more than five minutes in a Rip City Reddit thread lately, you know the vibe. It’s a mix of "Trust the Process" and "Wait, do we even own our own picks?" Ever since Joe Cronin sent Damian Lillard to Milwaukee, the spreadsheet for blazers future draft picks has started to look like a tax return from a billionaire's estate. It's messy. It’s confusing.
Honestly, it’s also the only thing keeping the lights on in Portland right now.
Most fans think the Blazers are just sitting on a mountain of Milwaukee assets. That’s true, kinda. But there’s a massive roadblock in Chicago that literally stops the front office from being able to trade their own picks for a star right now. If you want to understand where this team is actually going, you have to look at the protections, the swaps, and that annoying 2021 trade for Larry Nance Jr. that just won't die.
The Chicago Problem (And Why It Paralyzes the Blazers)
Let’s talk about the 2026 first-rounder first.
Basically, the Blazers owe a first-round pick to the Chicago Bulls. This is the "Larry Nance Jr. Debt." Because of the Stepien Rule—which says you can't be without a first-round pick in consecutive years—and the fact that this pick is protected 1-14 through 2028, the Blazers are effectively frozen. They can’t trade any of their own future firsts because no one knows exactly when the Bulls will finally get their pick.
If Portland stays bad (in the lottery), they keep their pick. If they make the playoffs, the pick goes to Chicago, and suddenly the "faucet" opens up for more trades.
It's a weird spot to be in. You want to be good enough to pay your debts, but you also want to be bad enough to land a top-five talent in a loaded 2026 draft class. If the pick doesn’t convey by 2028, it just turns into a second-rounder. But until then, Joe Cronin’s hands are sort of tied behind his back in the trade market.
The Milwaukee Gold Mine: Swaps and 2029
The Dame trade was the ultimate gamble on "future pain."
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Portland is betting that by 2028 and 2030, Giannis might be tired, or the Bucks might be old, or the salary cap might have absolutely nuked their depth. Here is what the cupboard actually looks like:
- 2028 Swap Rights: Portland can swap their pick for Milwaukee’s.
- 2029 Unprotected First: This is the crown jewel. No protections. If the Bucks bottom out, this is a top-three pick.
- 2030 Swap Rights: Another chance to jump the Bucks if they’re struggling.
But wait, there’s a catch.
In the deal for Deni Avdija, the Blazers actually traded the second most favorable of their 2029 picks to the Washington Wizards. Since Portland owns their own 2029, Milwaukee’s 2029, and Boston’s 2029 (from the Jrue Holiday flip), they get to keep the best one and the worst one. Washington gets the middle child.
It’s a galaxy-brain move that ensures Portland still has a potentially elite asset in 2029 while still being able to land a starting-caliber wing like Deni.
The Jrue Holiday Fallout: Boston’s Contribution
When Jrue was rerouted to the Celtics, it wasn't just about getting Robert Williams III and Malcolm Brogdon. It was about the 2029 unprotected first from Boston.
Think about that for a second.
Portland has three different chances to land a superstar in the 2029 draft. They have their own pick, Milwaukee's, and Boston's. Even if the Celtics are still winning 50 games a year by then, that's still another swing at the plate.
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Secondary Assets: The 2028 Magic Pick
Most people forget about the trade with Memphis where Portland sent out Cedric Coward (the 11th pick in '25) and got back Yang Hansen and a 2028 first-rounder via Orlando.
This is a huge deal.
Orlando is a young, ascending team, so that pick might not be a lottery selection, but having an extra first-rounders in 2028—the same year Portland has swap rights with Milwaukee—gives them a massive amount of flexibility. They could have three first-round picks in 2028 if everything breaks right.
Second Round Chaos: 2026 and 2027
The second-round situation is basically a game of Three-card Monte.
In 2026, the Blazers own a Memphis second-rounder (protected 31-42). Their own 2026 second is likely headed to Boston, San Antonio, or Washington depending on a complicated "most favorable" carousel.
By 2027, the Blazers have Atlanta's second and Minnesota's second.
Is a second-rounder going to save the franchise? Probably not. But look at Toumani Camara. He was a second-round "throw-in" in the Lillard deal and he’s turned into one of the best perimeter defenders the team has had in years. These picks matter for filling out the bench when the team eventually gets expensive.
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The Ownership Wildcard
There’s a massive elephant in the room: Tom Dundon.
Reports have been swirling that the Carolina Hurricanes owner could be taking over the Blazers as early as March 2026. If new ownership comes in, does the "patient rebuild" continue? New owners usually want to make a splash.
If the Blazers suddenly decide to trade for a star to pair with Scoot Henderson and Shaedon Sharpe, those blazers future draft picks from Milwaukee and Boston become the primary currency. They are the only way to get a seat at the table for a disgruntled All-Star.
What This Means for the 2026 and 2027 Seasons
The Blazers aren't in a "tank" anymore in the traditional sense. They are in a "debt-clearing" phase.
The goal for the next 18 months is simple: develop the young core so that they are good enough to actually convey that pick to Chicago in 2026 or 2027. Once that pick is gone, Portland regains control of its entire future.
Actionable Strategy for Following the Draft Assets
To stay ahead of the curve on Portland’s rebuild, watch these three specific variables:
- The Bulls' Record vs. The Blazers' Record: If Portland is sitting around the 10th or 11th seed, they are in the "Danger/Opportunity Zone." Making the play-in might actually be better for their long-term trade flexibility than finishing with the 5th worst record.
- Milwaukee’s Health: Every time Giannis or Dame misses a week of games, the value of those 2028 and 2029 picks skyrockets. These are currently the most discussed "non-Blazer" assets in the league.
- The 2029 "Middle" Pick: Keep an eye on the Wizards. Since they own the middle-valued pick of Portland's three 2029 firsts, their fans are actually incentivized to root for one of those teams (Blazers, Bucks, or Celtics) to be mediocre while the other two are either great or terrible.
Portland’s future isn't just about the guys on the floor; it’s about a collection of IOUs scattered across the Eastern Conference. It’s a slow burn, but for a small market team, it's the only way to build a sustainable contender without the luck of a #1 overall pick.
Track the Milwaukee Bucks' standings weekly. Their decline is directly correlated to the Blazers' ceiling. If the Bucks age out rapidly, Portland holds the most valuable "rebuild kit" in the NBA. Combine that with the eventual resolution of the Chicago debt, and the Blazers will have the ammunition to either draft a new dynasty or trade for the final piece of the puzzle.