Risky Trade Idea Solves Trail Blazers’ Crowded Backcourt Problem

The Portland Trail Blazers definitely have one of the NBA’s deepest backcourts, and that same depth might force them to make a difficult decision. Sports writer Jeremy Brenner recently proposed a blockbuster trade idea that would solve one of the Portland Trail Blazers’ biggest roster issues as they head into the 2026-27 season.

That trade would send Scoot Henderson, Shaedon Sharpe and Yang Hansen to the Milwaukee Bucks in exchange for former All-Star guard Tyler Herro and Caris LeVert.

Portland Trail Blazers Receive: Tyler Herro, Caris LeVert

Milwaukee Bucks Receive: Scoot Henderson, Shaedon Sharpe, Yang Hansen

The Trail Blazers created a backcourt logjam earlier this offseason by acquiring Ja Morant to join franchise icon Damian Lillard. That left Henderson, the No. 1 overall pick in the 2023 NBA Draft, without a clear path to becoming Portland’s starting point guard. Along with Henderson, the Blazers also have veteran Jrue Holiday.

That creates a massive logjam at the point guard position.

With Henderson entering the final year of his rookie contract before becoming a restricted free agent in 2027, this could be an ideal time for Portland to cash in on the talented young guard.

This Is A Very Risky Deal For The Blazers

For the Blazers, this deal would bring back an established scorer along with veteran wing Caris LeVert.

Herro is coming off another productive season, averaging 20.5 points, 4.8 rebounds, and 4.1 assists while shooting 48.0% from the field and 37.8% from three-point range. The former Miami Heat guard was traded to the Milwaukee Bucks earlier this offseason as part of the blockbuster Giannis Antetokounmpo trade and is entering the final year of his contract, where he will earn $33 million before hitting unrestricted free agency.

LeVert also adds depth on the wing. He averaged 7.4 points, 1.9 rebounds, and 2.7 assists while shooting 41.7% from the field and 33.3% from beyond the arc with the Detroit Pistons last season.

Like Herro, he was also acquired by the Milwaukee Bucks this summer as part of a six-team, 11-player deal. He is playing on an expiring contract worth about $14.8 million.

Herro is obviously the biggest attraction for the Blazers. The 26-year-old has established himself as one of the league’s better offensive guards, and he could eventually succeed Lillard as the starting shooting guard once the veteran reaches the end of his career. Herro’s off-ball scoring ability would also fit alongside Morant, giving the Blazers another perimeter threat without disrupting the offensive balance.

The Bucks Will Gladly Accept This Deal

The Bucks would be very happy with this trade because they would get two of the most promising young players.

Scoot Henderson averaged 14.2 points, 2.7 rebounds, and 3.7 assists while shooting 41.8% from the field and 35.2% from three-point range last season. Despite inconsistent production, the 22-year-old still has high upside, and that is one of the reasons the Blazers have kept him out of potential trade talks.

But Sharpe’s inclusion is what makes this deal hurt more for the Blazers.

The athletic wing had a breakout season, averaging 20.8 points, 4.3 rebounds, and 2.6 assists while shooting 45.2% from the field. His new four-year, $90 million extension starts next season, and Sharpe will make about $20 million in the 2026-27 season.

The Blazers would also have to part with young Yang Hansen, who averaged 2.2 points and 1.5 rebounds in his rookie season. He is still on his four-year, $21.3 million rookie contract and will make about $4.6 million next season.

The Blazers Have To Be Careful Before Committing To Such A Deal

This proposal would no doubt clear the Blazers’ crowded backcourt and provide more certainty around the rotation.

But for the Blazers, this trade might seem very complicated. Herro is a far more proven player today, but he is on an expiring contract. Unless the Blazers are confident they can sign him to a long-term extension, giving up Henderson, Sharpe and Hansen could be a very big gamble.

From the Bucks’ perspective, it is easy to see why this trade makes sense. After moving on from Antetokounmpo, the Bucks are shifting toward a younger core and a rebuild.

Henderson could develop into the point guard of the future, and Sharpe has a chance to become a primary scoring option. Hansen would also receive much more consistent playing time in Milwaukee than he has had in Portland so far.

Whether the Blazers think that a crowded backcourt is such a big issue that they need to trade three young talents remains to be seen. And that decision will certainly divide the front office and the fan base.