The Portland Trail Blazers are expected to be aggressive in improving their roster this offseason. They are without a single draft pick in what’s being called a “very deep” 2026 NBA Draft, and are also one of 23 teams that have access to both the full Mid-Level Exception (MLE), and the Bi-Annual Exception (BAE). That means Portland will have no advantage in free agency. Therefore, many feel the trade market is where the Blazers will make their big offseason splash.
Portland has never been connected
to as many high level trade rumors for its entire 56-year existence than they are currently. They own three years of control of the Milwaukee Bucks’ first round draft picks between 2028-2030. It’s widely expected that Milwaukee’s franchise icon, Giannis Antetokounmpo, will be traded this summer. The Blazers could factor heavily into that trade if Milwaukee is interested in regaining control of their draft future.
But what if the fabled Giannis deal doesn’t work out, at least not directly? There’s a second-best target the Blazers have been connected to: Boston Celtics wing Jaylen Brown.
What Can Brown Do For You?
An All-NBA player, Brown has been coveted by many Portland fans. A trade that once felt like a pipe dream may now have a realistic chance of happening. Holding young players and Milwaukee’s picks, the Blazers have the asset gravitas to have a seat at the big boy trade table for perhaps the first time ever.
Brown (29), is a NBA Champion, Finals MVP, and 5x All-Star who’s coming off his best individual season. He finished 6th in the league’s MVP vote, and averaged career highs with:
28.7 points
6.9 rebounds
5.1 assists
22.0 player efficiency rating
6.9 win shares
The Celtics were the number two seed in the Eastern Conference Playoffs, and were upset by the seventh-seeded Philadelphia 76ers 4-3 in the first round. Boston led the series 3-1 before collapsing for the first time in their rich history when holding a 3-1 lead. Losing in this fashion has sparked discussion that perhaps Boston has peaked with the “Jays”, Jayson Tatum and Jaylen Brown, as the foundation.
The two Celtics won their first title together only 2 seasons ago. Both are in their prime. Tatum missed most of this season recovering from a torn Achilles tendon, so the two of them had very little time to reestablish chemistry prior to the playoff flameout. Meanwhile, Brown’s career-best season led an overachieving Celtics squad in Tatum’s absence.
Celtics Searching for Rim Scoring
Usually, there would be no reason to break up Tatum and Brown, but team president Brad Stevens said this in his postseason press conference with NBC Sports Boston:
One of the things that we’ve got to figure out is how to have more of an impact at the rim, and I think we do need to add to our team to do that. I think the biggest thing is, can we generate looks at the rim?” Stevens said. “Yeah, everybody wants to do that, and every one of us would prefer a dunk over a 3. Every single one of us. Those are hard to get, and we struggle to generate them.
It’s an interesting quote for a couple reasons. The Celtics have ranked dead last in field goal attempts within 5 feet the past two seasons. Only 22% of their shots come in that range, but their scoring percentage in that zone is excellent at 69%. That’s second-best in the NBA. They just don’t have the players to create more opportunities.
Brown and Tatum only take 16-17% of their shots at the rim. In a league that cares about scoring mainly from the three-point arc (where the Celtics rank 4th) or at the rim (where they rank 28th) they need to seriously address their points in the paint.
Enter Antetokounmpo, who is one of the best players to ever be on the trading block. He represents the biggest cure for what ails the Celtics. Nobody takes more shots at the rim per game (11.8) or converts as many (8.9) at a higher percentage (75.7%). Boston has annual championship expectations, facing serious competition at the top in the Eastern Conference. After nine seasons with the Tatum and Brown core, it might be time for them to shake things up and make a big move.
The idea of pairing Antetokounmpo with Jayson Tatum is a sound one. When healthy, they are unquestionably two of the top ten players on the planet. One likes to attack the rim, and the other is a crafty shot creator all over the floor. Surround them with shooters and that is a tough offense to stop.
Reports suggest Giannis wants to both stay in the East and play on a contender. For the trade to work, it would require including one of Brown or Tatum in order to match salaries. Derrick White is Boston’s only other large tradable salary at $30 million, and he would likely need to remain as the third option in their attack.
What Does Milwaukee Want?
With Brown being the player on the move in this scenario, would the Bucks want to keep him, and would he want to go to Milwaukee?
Since the Bucks don’t control their draft future for the next 4 seasons, it makes some sense for them to stay competitive. Rebuilding or tanking only helps the New Orleans Pelicans and Trail Blazers who have that control over their draft picks.
It’s possible Milwaukee would try to make it work with Brown, Myles Turner, Bobby Portis, and Ryan Rollins. Brown did just lead a ragtag bunch of players to the second seed in the East. That team would be thin, though, with limited avenues to build further.
A Potential Blockbuster
Deni Avdija has experienced a meteoric rise to All-Stardom while playing on the league’s greatest value contract for two more seasons. With Avdija in place, adding a superstar makes sense in Portland. If they can’t trade for Antetokounmpo outright, then Jaylen Brown represents the next best potential star they could hope to land.
To make this three-way trade a possibility, Portland would send Jerami Grant and Shaedon Sharpe to Milwaukee for salary matching. (This would also open up the massive usage rate Brown requires.) Cronin would likely have to give back full control of the Bucks’ picks from 2028-2030. Kris Murray or Yang Hansen, plus a couple second-round picks could also go out in the deal. Boston would also likely have to send one or two first round picks to the Bucks. Milwaukee then regains flexibility to lean into a rebuild and start the work of offloading their veterans for future assets.
Brown’s Fit in Portland
The first order of business would be developing the chemistry between Brown and Avdija.
Both are unselfish, high-level, two-way stars. Establishing a cohesive offense would be a priority. The Blazers wouldn’t prosper with the “my turn, your turn” situation we sometimes see when stars are tossed together. Reuniting with Jrue Holiday might help smooth that process as he’s familiar with Jaylen’s and Deni’s playstyles. Holiday is the consummate chameleon for successfully navigating between two stars.
Brown is an average three-point shooter for his career, sitting at 35.8% on about 6 attempts per game. He ranked sixth in free throw attempts this season and shot a career high (79.5%), against a career 74% average. He and Avdija would put a huge strain on opposing defenses in this regard.
With Avdija attacking the rim, Brown could become a midrange assassin. That would leave Portland’s other players doing the heavy lifting from downtown. The return of Damian Lillard makes for a potentially explosive offense with his deep shooting gravity. If Dame remains an elite deep threat, teams will have to pick their poison with Brown and Avdija licking their chops to slice and dice while Lillard shoots outside.
Defensively, Brown is a massive upgrade over both Sharpe and Grant. He’s received All-NBA Defensive team votes each of the past 7 seasons. Portland would have the luxury of rotating between a defensive-oriented lineup with Holiday at point guard or an offensive one with Lillard.
It would be too early to forecast if this would make the Blazers good enough to get past the likes of the San Antonio Spurs, Oklahoma City Thunder, or even the Minnesota Timberwolves. However, any playoffs team adding both Jaylen Brown and Damian Lillard to it should rise in the conference.
Good Idea for the Future?
If this trade were to happen, Jaylen Brown is locked up for 3 more seasons on a max deal, which sees him through his age 32 season.
Portland has never been in position to trade for a superstar in their prime. Will Tom Dundon want to be this aggressive in his first offseason as owner? What becomes of the Blazers’ ceiling with this trade? Is Brown worth giving up Shaedon Sharpe, plus three potential solid lottery picks courtesy of the Milwaukee Bucks? Or should the Blazers stay on course with developing their young talent and sit on those draft picks for a future opportunity?
Weigh in with your comments!
